70 Essential Things to Do in Chicago (By a Local)

👉 Jump to: Best Things | Sites & Attractions | Museums & Culture | Outdoor Attractions | Food & Drink | Cool & Unusual | Hidden Gems | Entertainment & Nightlife | Hotel Finder Tool | Podcast | Get Printable Version

After just one trip to the Windy City, I found myself packing up and moving here. Almost five years later, I haven’t looked back. One of the reasons? There are truly endless things to do in Chicago.

Chicago has world-class restaurants, vibrant arts and culture, access to beautiful Lake Michigan, fantastic areas to stay, and it’s one of the best sports towns in America (and this is just for starters). At the end of the day, there’s something for everyone.

In this list, I share with you all the iconic attractions you can’t miss, plus some of my favorite local spots and activities that I always recommend to my friends and family. No matter your reason for visiting, you’re in for a treat – Chicago has it all.

Affiliate Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. See our Advertising Policy for further explanation. Thank you!

70 Best Things to Do in Chicago

Explore Chicago’s Neighborhoods

Experience the heart and soul of Chicago in its many diverse and unique neighborhoods.

📍 19 Best Chicago Neighborhoods

You may have heard that Chicago is a city of neighborhoods. It can be tempting to spend all your time sightseeing in Chicago’s downtown Loop if you’re a first-timer. But my #1 recommendation is this: Explore the neighborhoods. Because this is where the heart and soul of the city lies.  

Head to Lincoln Park for a family-friendly residential feel. There are tons of beautiful homes to stroll by and good shopping along Halsted and Armitage. Plus, Lincoln Park (the actual park) and the zoo are close by. 

The areas of Wicker Park, Bucktown, West Town, and Logan Square are popular with younger, artsier crowds. These neighborhoods are home to cool vintage shops, cafes, restaurants, and music venues.

Chinatown, Pilsen, and Ukrainian Village are just a few neighborhoods with rich, cultural roots. You’ll find delicious eateries, unique local shops, and more. 

Gold Coast and Old Town Triangle are great for admiring beautiful architecture. Plus, the lake is close. Go to Hyde Park if you love history and culture, and walk around the University of Chicago’s beautiful campus or stop by the Museum of Science and Industry. 

These neighborhoods are just for starters. See my guide to Chicago neighborhoods to explore deeper.

Millennium Park

See Chicago’s famous “Bean” and go sightseeing in the downtown Loop.

📍 Google Maps | Phone: (312) 650-8298 | Millennium Park Website | Hours: 6 am – 11 pm daily | Entrance: Free

Millennium Park is one of Chicago’s most iconic places (if not its most iconic place). It’s situated in the heart of downtown Chicago, also known as “the Loop.” Here, you can see Cloud Gate, or, as it’s better known, “The Bean.”

Millennium Park has a lot more to offer besides a picture with the Bean, though. All year round, you can walk the park, enjoy public art, and witness images at Crown Fountain – an interactive video sculpture. 

In the summer, enjoy outdoor concerts and Chicago festivals. Favorites include the Chicago Blues Festival and Millennium Park Summer Music Series, which take place at Jay Pritzker Pavilion. In the winter, you can go ice skating just below the Bean or at the nearby Maggie Daley ice skating ribbon.

Cloud Gate (“The Bean”)

Chicago’s most iconic landmark—a mirror-like art sculpture that locals call “The Bean.”

📍 Google Maps | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Cloud Gate, more commonly referred to as “The Bean,” is Chicago’s most identifiable landmark. This giant structure is located in Millennium Park. The Bean is best known for its shiny mirror-like surface, which was inspired by liquid mercury and designed to reflect images of the Chicago skyline above.

The Bean is a fun experience and a must-do on any Chicago itinerary if you’re a first-time visitor. I recommend stopping by for a quick picture in the morning or early evening for fewer crowds.

🖨️ Get a free, printable version of my 5-day Chicago itinerary here!

The Art Institute of Chicago

Enjoy a world-class collection of art in downtown Chicago.

📍 Google Maps | Phone: (312) 443-3600 | Art Institute Website | Hours: 11 am – 5 pm Wed, Fri-Mon, 11 am – 8 pm Thu, Closed Tue | Entrance: $32 for adults, $26 for seniors and students, Free for children (discounts available for Illinois & Chicago residents)

The Art Institute of Chicago is located in the Loop just south of Millennium Park. This world-class museum features thousands of artworks from around the world, spanning centuries and styles. Think of artists like Van Gogh, Monet, and Picasso, just to name a few. 

Plan to spend at least a few hours wandering the Art Institute. The historic building has four levels in total, with numerous wings and exhibitions to explore. Some of my favorite exhibits are the Impressionism collection and the Thorne Miniature Rooms.

Note that because of its size, young children and seniors may become tired. Tickets can be purchased online and in advance, but they may also be purchased on-site. If you’re a big art enthusiast, you may consider purchasing an exclusive guided skip-the-line tour to make the most of your visit.

👉 Pro Tip: I’ve found that one of the best ways to see and navigate a museum of this size is to start on the top floor and work your way down.  

Wrigley Field

Attend a baseball game at one of America’s most famous ballparks.

📍 Google Maps | Phone: (800) 843-2827 | Wrigley Field Website | Hours: On game days, gates open 2 hours before the first pitch | Tickets: Ranging from $14 – $119 

Chicagoans take their sports seriously, and this obviously includes Wrigley Field – home of the Chicago Cubs. This famous stadium is the second oldest Major League baseball field in America. It was built in 1914 and is located in the North Side neighborhood of Wrigleyville.

Throughout its history, the ballpark has witnessed so many historic moments, from Babe Ruth “calling his shot” in 1932, to “reversing the curse” in 2016. Not to mention, the Cubs have won three World Series titles and longstanding traditions are a key part of the experience.

The stadium itself has brick walls covered in ivy, as well as a beloved red marquee on display out front. As an ode to the beginnings of baseball, the scoreboard is manually operated.

Order some snacks or Chicago-style hot dogs if that’s your style. Although, to avoid some craziness, plan on getting lunch and drinks before your game.

🚗 How to Get There: Parking can be a nightmare so a better option is to use the CTA Red Line or rideshare options for transportation. Just note that the train will most likely be packed and rideshares can get pricey around game time.

Take an Architecture Cruise

Journey through Chicago’s history and architecture and enjoy amazing downtown views.

📍 Google Maps | Phone: (312) 222-9328 | Shoreline Sightseeing Website | Hours: departure times vary | Entrance: $40.95 adults, $26.95 children | 👉 Chicago Architecture River Cruise

An architecture cruise is a must for first-time visitors and even local residents. This tour shows off the city’s beauty and tells the story of Chicago’s history. It’s suitable for all ages and interests.

Tours last about an hour and you can expect to sit back and relax while an enthusiastic guide narrates Chicago’s story of the past and present. You’ll pass iconic buildings while floating down the Chicago River and be able to snap pictures from the comfort of your seat.

You’ll leave with a better understanding of the city, its history, architecture, and so much more. If you don’t know where to start planning, this is a great activity to kick off your trip.

Lakefront Trail

Run, walk, or bike along beautiful Lake Michigan on this 18-mile urban trail.

📍 Google Maps | Phone: (312) 742-7529 | Lakefront Trail Website | Hours: Open 24 hours a day | Entrance: Free | 👉 Chicago Ultimate City Bike Tour

Lake Michigan is arguably my favorite part of living in Chicago. And enjoying Lake Michigan also means taking advantage of our amazing Lakefront Trail. This paved path runs for 18 miles along the city and shoreline, providing incredible views. The trail is free to everyone and perfect for walking, running, and biking.

In the summer, you can easily access Chicago’s beaches via the Lakefront Trail. In the winter, part of the lake freezes over and creates icy waves along the shore. Even if you get busy sightseeing during your visit, set aside time for the Lakefront Trail. Trust me!

Chicago Riverwalk

Take a leisurely stroll through the heart of Chicago.

📍 Google Maps | Phone: (877) 300-6746 | Chicago Riverwalk Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Chicago Riverwalk is a 1.25-mile urban trail that lines the Chicago River on the northern side of the Loop. This pedestrian path is one of my favorite ways to sightsee downtown. It’s free, open year-round, and lined with restaurants, bars, cafes, shops, and more. 

This is a great place to take a scenic, leisurely stroll, or sit down somewhere for a picnic or quick rest. You can access the Riverwalk via multiple entry points off of E Wacker Drive. Just head down to the river and find the signs marked “Chicago Riverwalk.”

👉 Did You Know? Every year for St. Patrick’s Day, the Chicago River is dyed green!

Chicago Sites & Attractions

Navy Pier

Enjoy a day of views, attractions, and fun for the whole family.

📍 Google Maps | Phone: (312) 595-7437 | Navy Pier Website | Hours: Varies by season | Entrance: Free (entry fees for attractions and rides may vary) | 👉 Fireworks Kayak Tour

Navy Pier extends out into Lake Michigan and offers activities and restaurants for the whole family to enjoy. It’s a great spot for snapping pictures of the lake and Chicago skyline.

Some of the popular activities and attractions at the pier include: Cruise tours, the Centennial Ferris Wheel, the Chicago Children’s Museum, Chicago Shakespeare Theater, and Navy Pier Beer Garden. You can also enjoy two nearby parks. Polk Bros Park hosts free events and programs and Milton Lee Olive Park provides beautiful skyline views. 

Navy Pier offers seasonal attractions such as fireworks in the summer and Light Up The Lake in the winter (an indoor light garden). For more, check out my full guide to visiting Navy Pier.

Magnificent Mile

Shop your heart out and take in the sights.

📍 Google Maps | Phone: (312) 642-3570 | Magnificent Mile Website | Hours: Open daily, shop hours may vary | Entrance: Free

If you’re looking to do some luxury shopping and hit up those big-name stores, then pay a visit to the Magnificent Mile. This mile-long stretch is located on North Michigan Avenue, packed with shops, restaurants, luxury hotels, and more. 

Although a bit touristy, it’s worth visiting for anyone with an itch to shop. Not to mention, it’s close to the lakefront and only a short walk to the Chicago River for some sightseeing before or after.

While you browse the Magnificent Mile, be sure to take in some of the historic buildings along the way like the Chicago Water Tower, Tribune Tower, and Wrigley Building.

Now, If shopping isn’t your thing but you don’t want to miss out, check out this Magnificent Mile Walking Tour to experience the avenue from a historical point of view.

Lincoln Park Zoo

Come face to face with wildlife.

📍 Google Maps | Phone: (312) 742-2000 | Lincoln Park Zoo Website | Hours: 8 am – 5 pm Mon-Fri, 8 am – 7 pm Sat-Sun | Entrance: Free 

Get up close and personal with animals at Lincoln Park Zoo. Entry is totally free and the zoo is located in the heart of Lincoln Park. Almost 200 species of animals from around the world can be found here — bears, crocodiles, hippos, and everything in between. 

Most habitats are designed for visitors to observe the animals in their own environment, but a few interactive opportunities are available, too. The zoo is fairly easy to navigate, so if you plan on seeing all the exhibits, plan on spending around two hours here. 

👉 Pro Tip: Although the zoo is free, parking can range from $20-$35. If you want to avoid this cost, I recommend taking public transportation to the nearest train or bus stop. Or, if your accommodations are nearby, walk here.

Willis Tower Skydeck

Take in sweeping views of the Windy City.

📍 Google Maps | Phone: (312) 875-9447 | Skydeck Website | Hours: Varies by season | Entrance: $32 adults, $22 children, Free for ages 3 and under | 👉 Skydeck ticket

For breathtaking views of Chicago, head to Willis Tower in the Loop. Formerly known as Sears Tower, this 108-story building is the tallest building in all of Chicago and the second tallest building in North America.

The Willis Tower Skydeck and Ledge is located on the 103rd floor and is a family-friendly way to take in the city below. Upon entrance, you’ll weave through educational displays and exhibits designed to give you a taste of Chicago’s history. This is all leading up to the main Skydeck itself where you’ll see the city through floor-to-ceiling windows. 

If you’re not afraid of heights, step out on the Ledge. This 4.3 feet glass box extends out over the city for views in every which way – on a clear day you might be able to see four states!

👉 Pro Tip? Definitely take the weather into account when visiting Willis Tower. For the best views, visit on a clear day.

360 Chicago Observation Deck

Take a tilt over Chicago.

📍 Google Maps | Phone: (888) 875-8439 | 360 Chicago Website | Hours: 9 am – 11 pm daily | Entrance: $44 – $58 for ages 12+, $34 – $38 for ages 3 – 11 | 👉 360 CHICAGO ticket

Looking to take in the Chicago skyline from a new perspective? At the 360 Chicago Observation Deck, you can do just that. 

From the 94th floor of 875 N Michigan Avenue (formerly John Hancock Center), you’ll be met with 360-degree views of the city, lake, and surrounding areas. Because of the building’s location, you’ll have especially close views of the Magnificent Mile and Lake Shore Drive. 

For an extra wow factor, take a ride on Tilt. This attraction will tilt you more than 1000 feet over the Magnificent Mile on Michigan Avenue. If you have a fear of heights, then this might not be the experience for you. But for most visitors, regardless of age, this is a unique and thrilling experience.

👉 Pro Tip: Similar to Willis Tower, I recommend visiting the John Hancock Center on a clear day. You’ll get the most out of your money and witness the best views. 

Shedd Aquarium

Experience what’s under the surface.

📍 Google Maps | Phone: (312) 939-2438 | Shedd Aquarium Website | Hours: 9 am – 5 pm Mon, Thu-Fri, 9 am – 9 pm Tue, 9 am – 10 pm Wed, 9 am – 6 pm Sat, 11 am – 6 pm Sun | Entrance: $20 – $40 for ages 12+, $15 – $30 for ages 3 – 11, Free for ages 3 and under 

In addition to the Lincoln Park Zoo, Chicago has its own state-of-the-art aquarium. The family-friendly facility is located right on the water along Chicago Harbor. This 5-million-gallon aquarium houses aquatic life from around the world including animals native to the Great Lakes.

There is a wide variety of exhibits to explore like the Abbott Oceanarium, Wild Reef, Caribbean Reef, and more. Children can even enjoy interactive experiences where they can touch Stingrays, Sea Stars, and Sturgeons. There are also dolphin shows throughout the day, every half-hour.

Shedd Aquarium is located next to the Field Museum and Adler Planetarium, in case you want to plan a whole day around these attractions.

Adler Planetarium

Travel through space and time.

📍 Google Maps | Phone: (312) 922-7827 | Adler Planetarium Website | Hours: 9 am – 4 pm Thu-Tue, 4 pm – 10 pm Wed | Entrance: $25 – $40 for adults, $13 – $28 for ages 3 – 11 

Did you know that Adler Planetarium was the first planetarium in America?

Here, take in the universe and learn all about astronomy. This museum and historical landmark is located on Northerly Island at the base of Chicago Harbor. It’s right next to the Field Museum and Shedd Aquarium.

Adler Planetarium is family-friendly and an interactive experience for everyone. Theater programs are shown every day and educational events happen throughout the year. Popular exhibits include Astronomy in Culture, Chicago’s Night Sky, Our Solar System, and more.  

ART on THE MART

Watch this iconic architectural attraction light up with color and movement.

📍 Google Maps | Phone: (800) 677-6278 | ART on THE MART Website | Hours: Varies by season | Entrance: Free 

ART on THE MART is the largest digital art projection in the world. It runs every night between April and December. Art collections rotate throughout the year, so there’s always a new light show to see. 

I recommend making a whole evening out of ART on THE MART. Grab dinner along the river beforehand, and then find a spot to sit or stand on the Chicago Riverwalk across from the iconic building. Then, watch as thousands of light projections cast colorful, moving artworks on the facade of THE MART. It’s a truly unique experience!

Crown Fountain

A digital and interactive art display in Millennium Park.

📍 Google Maps | Phone: (312) 742-1168 | Website | Hours: 6 am – 11 pm daily | Entrance: Free 

Crown Fountain is a digital art display on two 50-foot-tall towers. These towers are located in Millennium Park and are best known for displaying the “Faces of Chicago.” 

These locals’ faces are meant to be a modern take on gargoyles. Similarly, water flows out of the “mouths” of the diverse faces displayed. Crown Fountain was designed by Spanish artist, Jaume Plensa. It’s a unique landmark and a nice spot to cool off during the summer.

Chicago Museums & Cultural Attractions

👉 Bookmark our full list of the 20 best museums in Chicago!

Museum of Science and Industry

One of the largest science museums in the world (seriously… it’s massive).

📍 Google Maps | Phone: (773) 684-1414 | Website | Hours: 9:30 am – 4 pm daily | Entrance: $25.95 adults, $14.95 for ages 3-11 | 👉 Discounted Admission with Chicago CityPASS

The Museum of Science and Industry (MSI) is one of Chicago’s best museums. It’s located in Jackson Park on Chicago’s South Side and is one of the largest science museums in the world. 

Visitors of all ages will enjoy MSI. There are endless interactive exhibits about science, innovation, and engineering feats from around the globe and throughout history. Even if you don’t think these things sound interesting, give this museum a try. I’m more of an art and history person myself, but I still love MSI. 

The Coal Mine, U-505 Submarine, and the Mirror Maze are popular permanent exhibits. But there are exciting new temporary exhibits each year. Be sure to block out an entire morning or afternoon to visit MSI. The museum is huge and you’ll want 2-4 hours.

Museum of Contemporary Art

Engage with contemporary art exhibits designed to make you think.

📍 Google Maps | Phone: (312) 280-2660 | Museum of Contemporary Art Website | Hours: 10 am – 9 pm Tue, 10 am – 5 pm Wed – Sun, Closed Mon | Entrance: $22 for adults, $14 for students, teachers, and seniors, Free for ages 18 and under

Unlike the Art Institute of Chicago, the Museum of Contemporary Art (MCA) features constantly rotating exhibitions by contemporary artists of today. I’ve been to MCA countless times, and enjoy different and thought-provoking exhibits on every visit.

This museum is family-friendly, but students and adults may especially appreciate the more nuanced, and often heavier, subject matter. Still, there is artwork for everyone to enjoy. The museum also offers live performances, events, and programs for the community. Expect to spend around an hour to two hours here. 

Field Museum

Immerse yourself in some natural history.

📍 Google Maps | Phone: (312) 922-9410 | Field Museum Website | Hours: 9 am – 5 pm daily | Entrance: $21 – $30 for adults, $14 – $23 for children ages 3 – 11, Free for ages 2 and under | 👉 Field Museum admission

The Field Museum is located just south of Grant Park near the Shedd Aquarium, Adler Planetarium, and Soldier Field. This massive museum is home to almost 40 million specimens and artifacts such as T-Rexes, meteorites, animal biology, and more.

This museum is especially family-friendly and aimed at immersing children in science and discovery. 3D movies are shown for the whole family to learn from so plan to spend an entire morning or afternoon here. 

A visit to the Field Museum is a great way to experience natural wonders and history all in one afternoon.

Chicago Children’s Museum

Let your kids play, learn, and explore to their hearts’ content.

📍 Google Maps | Phone: (312) 527-1000 | Chicago Children’s Museum Website | Hours: 10 am – 5 pm daily | Entrance: $21 resident, $25 non-resident

At the Chicago Children’s Museum, children of all ages can enjoy a space to play and learn. This museum at Navy Pier comprises more than a dozen exhibits that cater to different interests and experiences.

For some math, science, and discovery, exhibits like Tinkering Lab, Skyline, and Dinosaur Expedition will allow children to tinker, build mini-skyscrapers, and even dig for dinosaur bones. At the Art Studio, children can let their imaginations soar with painting, drawing, and pottery-inspired workshops. 

Additionally, children can learn practical life skills and take the lead at exhibits like Kids Town and Michael’s Museum. And for just plain fun, there are tons of areas for your little ones to climb, play, explore, and learn. 

Chicago History Museum

Uncover Chicago’s history at this museum near Lincoln Park.

📍 Google Maps | Phone: (312) 642-4600 | Chicago History Museum Website | Hours: 9:30 am – 4:30 pm Tue – Sat, 12 – 5 pm Sun, Closed Mon | Entrance: $19 for adults, $17 for students and seniors, Free for ages 18 and under (Illinois residents) 

The Chicago History Museum is located right near the lake in the southeastern corner of Lincoln Park. One of Chicago’s oldest cultural institutions, a visit here will walk you through the city’s historic past to learn about what makes Chicago, well, Chicago. 

Exhibits explore topics like freedom, democracy, and the history of Abraham Lincoln. A film is available to learn about the city’s growth and events like the Great Chicago Fire of 1871. There’s even an exhibit for uncovering the city through the five senses.

Overall, this is the perfect museum for first-time visitors and residents alike, since it offers a better understanding of the city.

National Museum of Mexican Art

Appreciate Mexican art and culture at this free Pilsen museum.

📍 Google Maps | Phone: (312) 738-1503 | Museum of Mexican Art Website | Hours: 10 am – 5 pm Tue – Sun, Closed Mon | Entrance: Free

The National Museum of Mexican Art located in the Pilsen neighborhood is home to one of the largest collections of Mexican art in the country. This museum, which first opened in 1987, features both permanent and rotating art exhibitions, as well as cultural performances, films, and programs. 

Although the museum may be especially appreciated by members of the Mexican community, it is open to those of all ages and backgrounds. Visiting is a great way to learn, support, and appreciate Mexico’s rich history and vibrant artwork.

Chicago Cultural Center

Learn about a historical landmark and attend free public events.

📍 Google Maps | Phone: (312) 744-5000 | Chicago Cultural Center Website | Hours: 10 am – 5 pm daily | Entrance: Free

The Chicago Cultural Center is one of Chicago’s (and the nation’s) most comprehensive cultural centers. Built in 1897, this historic Chicago landmark serves as a cultural destination for the public.

The building itself has two beautiful stained-glass domes and intricate architectural details throughout, making it an absolute marvel. The building’s south dome is actually the largest stained-glass Tiffany dome in the world! If you’re interested in history, arts, and culture, then this is a good stop to make.

The center’s main focus is bringing free events for everyone to enjoy. This includes art performances and exhibitions, lectures, and cultural events. Guided tours are also available. 

Free guided tours are offered on Thursdays and Fridays at 1:15 pm. If you want to go more in-depth, though, consider this architectural interiors tour that includes the Cultural Center. It has over a thousand 5-star reviews!

The Rookery Building

This 19th-century building in the Loop is one of Chicago’s most important landmarks. 

📍 Google Maps | Phone: (312) 553-6100 | Website | Hours: 6 am – 6 pm Mon – Fri, 8 am – 2 pm Sat, Closed Sun | 🎫 Tour: $12-$17

The Rookery Building is one of Chicago’s coolest buildings. It’s a stellar example of the city’s architectural boom that followed the Great Chicago Fire of 1871. The Rookery Building is considered by many to be an “architectural masterpiece.” 

The building itself was designed by Daniel Burnham and John Root. However, Chicago architect Frank Lloyd Wright had his hand in redesigning the lobby in 1905. 

You don’t have to be a lover of architecture and design to appreciate how beautiful the Rookery Building is. The spiral Oriel Staircase is the highlight for most people. It’s stunning. The Light Court lobby is beautiful, too. 

DuSable Museum of African American History

Visit this compelling museum about African American history in Chicago and beyond. 

📍 Google Maps | Phone: (773) 947-0600 | Website | Hours: 10 am – 5 pm Tue – Sun, Closed Mon | Entrance: free

The DuSable Museum of African American History is located in Washington Park on Chicago’s South Side. This museum is one of the oldest African American museums in America.

Here, you’ll learn about African American history in Chicago and beyond. The exhibits contain historic artifacts and artwork, along with thought-provoking media presentations. 

For example, the DuSable Museum previously held a virtual reality exhibit on Martin Luther King Jr.’s “I Have A Dream” speech from 1963. Other exhibits have ranged from fashion objects to stories of the African diaspora. 

The DuSable Museum of African American History is right next to the University of Chicago’s campus. Check out the museum while you explore the university area. 

Richard H. Driehaus Museum

Wander through the ornate rooms within this Gilded Age mansion and museum near the Magnificent Mile.

📍 Google Maps | Phone: (312) 482-8933 | Website | Hours: 11 am – 7 pm Wed, 11 am – 5 pm Thu-Sun, Closed Mon & Tue | Entrance: $20 adults, $15 seniors, $10 students, free for ages 12 and under

Richard H. Driehaus Museum is a small mansion museum in downtown Chicago, just a couple of blocks away from the Magnificent Mile. This historic Chicago building was built in 1883. It was home to Samuel and Matilda Nickerson, a wealthy and influential Chicago couple. 

The Gilded Age mansion is best known for its marble detailing and ornate design. Everything is exquisite, from the stained glass windows and dome to the intricate woodworking details. A $5 guided tour is the best way to experience this historic gem.

International Museum of Surgical Science

Explore the history of surgery through informative exhibits, art, and artifacts in this Gold Coast museum (but it’s not for the squeamish!).

📍 Google Maps | Phone: (312) 642-6502 | Website | Hours: 9:30 am – 5 pm Mon-Fri, 10 am – 5 pm Sat & Sun | Entrance: $25, adults 

Let me be upfront – I don’t like this museum. But not because it’s a bad one! It’s just not for those who are squeamish, which includes myself. That being said, people who have an interest in surgery, medicine, and science will love this museum. 

I took my mom (who isn’t squeamish like me) and she was fascinated by the historic artifacts and exhibits. The 19th Century Apothecary, Hall of Immortals, and iron lung are highlights. But you’ll also find things like a jar of gallstones (gross but attention-grabbing for sure!)

The museum itself is housed in a historic mansion along the lakefront in Gold Coast. Fun fact: it was built to resemble a chateau on the grounds of Versailles in France. The architecture is certainly impressive. [source]

University of Chicago

Chicago’s premier university in Hyde Park has a beautiful campus filled with Gothic architecture.

📍 Google Maps | Phone: (773) 702-1234 | Website | Entrance: Free 

The University of Chicago (UC) is the Windy’s City’s premier private university. It’s located on Chicago’s South Side in Hyde Park. You don’t have to be a student to visit or appreciate the beautiful campus. It’s filled with Gothic-style architecture and other unique buildings worth checking out. 

Highlights include Bond Chapel, Rockefeller Memorial Chapel, and Cobb Lecture Hall. The Joe and Rika Mansueto Library is a cool, modern building where scenes from the 2014 movie Divergent were filmed. Other highlights include the Frederick C. Robie House and Smart Museum of Art.

Frederick C. Robie House

This iconic Prairie-style home in Hyde Park was designed by famed Chicago architect Frank Lloyd Wright.

📍 Google Maps | Phone: (312) 994-4000 | Website | Hours: 9:30 am – 4 pm Thu – Mon, Closed Tue & Wed | 🎫 Tour: $20-$75 | 👉 Robie House Admission

Frederick C. Robie House is an iconic landmark in terms of Chicago architecture and design. It was designed by famed Chicago architect Frank Lloyd Wright and is best known for showcasing his Midwestern Prairie style. 

The Robie House, as locals call it, was built in 1910. Today, it’s a museum where you can witness this Prairie-style architecture up close. Tours show off the exterior and interior, including its unique woodwork. 

Fans of architecture and design will especially appreciate the home. It’s also located on the University of Chicago’s campus, so be sure to wander around for more unique architectural sights.

Frank Lloyd Wright Home & Studio

This historic Prairie-style home and studio in Oak Park was designed by famous Chicago architect Frank Lloyd Wright. 

📍 Google Maps | Phone: (312) 994-4000 | Website | Hours: 10 am – 4 pm daily | Entrance: $20-$75 | 👉 Frank Lloyd Wright Home & Studio Tour Ticket

The Frank Lloyd Wright Home & Studio is exactly what it sounds like: the home and studio of prominent Chicago architect, Frank Lloyd Wright. Fans of architecture and design will especially appreciate this spot. 

You need to book a tour to visit. Tours are about an hour long and are led by knowledgeable guides. This is a great opportunity to learn more about Frank Lloyd Wright and his iconic Prairie-style architecture and design. The home’s unique interior details like the woodwork and use of natural light are what make this place so cool. 

This museum is located a bit outside the city in Oak Park. It’s a good place for a mini-day trip. You can reach this museum by car, but you can also take the train via the Green Line to Oak Park. 

Ernest Hemingway’s Birthplace Museum

Visit the birthplace and childhood home of famous American author Ernest Hemingway.

📍 Google Maps | Phone: (708) 445-3071 | Website | Hours: 1 pm – 5 pm Thu-Fri & Sun, 10 am – 5 pm Sat, Closed Mon-Wed | Entrance: $20 adults, free under 10 | 👉 Public Tour-Adult Admission Ticket

The Ernest Hemingway Birthplace Museum is the birthplace and childhood home of famed American author Ernest Hemingway. Literature and history lovers will especially love this place.

Ernest Hemingway was known for being an adventure-seeking world traveler, but his life started just outside of Chicago in Oak Park. This home and birthplace museum showcases Hemingway’s life and career. You can walk through the Victorian-style house to feel what life was like for young Hemingway and see some artifacts as well. 

The Ernest Hemingway Birthplace Museum is just a stone’s throw from the Frank Lloyd Wright Home & Studio in Oak Park. Combine both of these museums into one visit.

👉 Want to Explore Beyond Chicago? See my guide to the best day trips from Chicago.

Outdoor Attractions in Chicago

Grant Park

Visit one of Chicago’s biggest cultural hubs.

📍 Google Maps | Phone: (312) 742-3918 | Grant Park Website | Hours: 6 am – 11 pm daily | Entrance: Free 

Known as downtown Chicago’s “front lawn,” Grant Park is a cultural hub that spans over 300 acres. In many ways, it’s the central, go-to place for a nature escape downtown as it’s also home to Millennium Park and Maggie Daley Park. 

This vast green space is more than just a park, though. Some of the city’s top attractions all converge in this one place.

Besides Cloud Gate and everything within Millennium and Maggie Daley Parks, the Art Institute of Chicago, Lakefront Trail, and Buckingham Fountain can all be found here.

And throughout the year, Grant Park hosts a plethora of Chicago festivals including Taste of Chicago, SummerDance, and most notably, Lollapalooza.

North Avenue Beach

Spend an afternoon on the shores of Lake Michigan.

📍 Google Maps | Phone: (312) 742-5121 | North Avenue Beach Website | Hours: 11 am – 7 pm daily | Entrance: Free 

Planning on visiting in the summer? I highly recommend carving out some beach time along Lake Michigan. Specifically, head to North Avenue Beach. 

Though it can get crowded on hot days, this Chicago beach is close to downtown and falls along the Lakefront Trail. Volleyball courts and water sports rentals are available here.

North Avenue Beach also features incredible views of the city and lake. Walk out on the concrete pier to take in the picturesque skyline and bright blue water.

Bloomingdale Trail “The 606”

Take a walk along Chicago’s urban greenway.

📍 Google Maps | Phone: (312) 742-4622 | 606 Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Bloomingdale Trail, better known as “The 606,” is a 2.7 mile-long walking trail that extends west from Ridgeway Ave, and then east to Ashland Ave.

This trail, which was transformed from an old rail line, offers a refreshing outdoor escape and is perfect for runners, bikers, and anyone who wants to enjoy a nice stroll. 

There are 12 entry points to reach the trail from. Depending on where you stay in Chicago, the easiest way to reach the 606 is by taking the Blue Line to the Damen or Western stops. From either of these train stops, you can easily access the trail.

If you’re looking to get a little exercise in while still enjoying the city, head to the 606!

Maggie Daley Park

A family-friendly park in downtown Chicago, home to several recreational activities. 

📍 Google Maps | Phone: (312) 742-3918 | Website | Hours: 6 am – 9 pm daily | Entrance: Free 

Visiting Maggie Daley Park is great if you are visiting Chicago with kids. This park is located in the northeastern corner of Grant Park and contains numerous recreational areas. 

There’s a playground or “play garden,” a climbing wall, a mini golf course, tennis courts, sidewalks for biking and scootering, ice skating rinks in the winter, and picnic areas. There’s also a fieldhouse, cafe, and Cancer Survivors’ Garden. 

Simply put, Maggie Daley Park is one of the best places in Chicago to let your kids play and explore freely.

Lincoln Park Conservatory

A vibrant and blooming greenhouse in Lincoln Park that’s free to visit.

📍 Google Maps | Phone: (773) 883-7275 | Website | Hours: 10 am – 4:30 pm Wed – Sun, Closed Mon & Tue | Entrance: Free (online reservations required)

Lincoln Park Conservatory is a free greenhouse in Lincoln Park. It can be explored in about an hour, and it’s a great place to visit if you’re looking for a change of scenery and some peace within the city (it’s also perfect for warming up if you visit in the winter). 

The greenhouse contains different garden houses. This includes the Orchid House, Fern Room, a room for special exhibits, and the Palm House — my favorite. Be sure to reserve tickets to the Lincoln Park Conservatory online ahead of time.

Alfred Caldwell Lily Pool

A hidden lily pool in Lincoln Park that’s inspired by the Midwestern prairie. 

📍 Google Maps | Phone: (773) 883-7275 | Website | Entrance: Free

Alfred Caldwell Lily Pool is often overlooked in Lincoln Park. This lily pool and pavilion provide a small, but serene escape from the noise of the city. It was designed by landscape architect Alfred Caldwell and meant to look like a Midwestern prairie. 

It’s free to visit Alfred Caldwell Lily Pool. Come here to sit, relax, and enjoy a restful moment, or even bring a book. I recommend visiting the lily pool in conjunction with the Lincoln Park Conservatory and Lincoln Park Zoo. All three are totally free!

Jackson Park

Find some peace and tranquility in nature at this enormous park, located within the Hyde Park neighborhood.

📍 Google Maps | Entrance: Free 

Before or after you visit the popular Museum of Science and Industry, take a stroll around Jackson Park. This gigantic green space in Hyde Park is home to beautifully landscaped areas, recreation fields and facilities, beaches, a dog park, and more. I especially recommend the Japanese Garden in the center of the park, right behind MSI. 

Garfield Park Conservatory

Experience a natural oasis just outside the city.

📍 Google Maps | Phone: (773) 638-1766 | Garfield Park Conservatory Website | Hours: 10 am – 8 pm Wed, 10 am – 5 pm Thu – Sun, Closed Mon & Tue | Entrance: Free (online reservations required)

Garfield Park Conservatory in Garfield Park is located about halfway between downtown Chicago and Oak Park. This conservatory, which is one of the largest in the country, is a beautiful place to witness nature and plants from around the world. In total, the conservatory has 2 acres of greenhouse space and 10 acres of garden.

Plan on spending one to three hours wandering this nature oasis. Popular garden collections include the Palm House, Desert House, and Fern House. The conservatory also offers exhibit and installation events, and educational programs. 

Overall, the Garfield Park Conservatory is the perfect nature escape from Chicago. 

Oz Park

A serene, yet playful neighborhood park that’s great for picnicking, play, and exploring Lincoln Park.

📍 Google Maps | Phone: (312) 742-7898 | Website | Hours: 6 am – 11 pm daily | Entrance: Free

Oz Park is a recreational park set in the heart of the Lincoln Park neighborhood. Its Wizard of Oz theme makes it fun for families, but it’s good for anyone who wants to relax or enjoy some recreation. 

Mostly locals frequent the park, but its open green spaces, benches, and walking paths make it a nice change of pace for locals and visitors alike. There are also tennis/pickleball courts and baseball and soccer fields on-site. I love coming here in the summer to play tennis or volleyball with friends.

Food & Drink in Chicago

Lou Malnati’s Pizzeria

Pizza the Chicagoan way.

📍 Google Maps | Phone: (312) 828-9800 | Lou Malnati’s Website | Hours: Vary by location

Deep-dish pizza is a distinctly Chicagoan food. This style of pizza is sometimes referred to as “Chicago-style pizza” and is made with a thick crust, and stacked with layers of sauce, cheese, and toppings. The layers are even placed on the dough backward, with cheese placed first and sauce topped off last. 

If you’re looking to taste a classic deep dish, then head to Lou Malnati’s. They have multiple locations and are one of the oldest deep-dish pizzerias in Chicago. Their pizzas are known for their made-from-scratch, flaky, buttery crusts, and fresh ingredients. The restaurants are casual and family-friendly.

👉 Pro Tip: Deep dish pizza can take a while to bake, so plan for a little extra time. 

Time Out Market

Options for everyone to enjoy.

📍 Google Maps | Phone: (312) 637-3888 | Time Out Market Website | Hours: 10 am – 10 pm Mon – Sat, 10 am – 9 pm Sun

Time Out Market is a food hall located in the Fulton Market District in West Loop. Here, some of Chicago’s best restaurants, bars, and bakeries have vendor stalls all under one roof. You’ll find a wide array of cuisines!

If you’re traveling in a group, this is a great option to satisfy different taste buds. Everyone can order something unique but still enjoy a meal together. 

No reservations are needed, but depending on what time you eat here, you may have to scour around for some seats. I recommend having someone from your group secure a spot and then taking turns to order.

If you’re interested, the upstairs level of the building serves as an event space with a steady lineup of guests and programs.

Starbucks Reserve Roastery

Enjoy specialty drinks and food at the largest Starbucks in the world.

📍 Google Maps | Phone: (312) 283-7100 | Hours: 6:30 am – 8 pm Mon – Thu, 8 am – 9:30 pm Fri – Sun 

The Starbucks Reserve Roastery in Chicago is the largest Starbucks in the world! It’s located on Michigan Avenue along the Magnificent Mile. 

There are five floors to this Starbucks Reserve. You’ll find a gift shop, a coffee bean scooping station, a bakery & cafe, an experimental coffee bar, a cocktail bar, and a rooftop terrace. 

I recommend trying something different, like the pastries, savory dishes, or cocktails. Just be prepared to potentially wait in a long line, as visiting this Starbucks Reserve is a bit touristy.

Cindy’s Rooftop

This trendy rooftop bar that overlooks Grant Park offers sprawling city views. 

📍 Google Maps | Phone: (312) 792-3502 | Website | Hours: 11 am – 11 pm Mon – Thu, 11 am – 12 am Fri, 10 am – 12 am Sat, 10 am – 11 pm Sun 

Cindy’s Rooftop is an awesome Chicago bar for its rooftop views alone. It’s located on the 13th floor of the Chicago Athletic Association, which is a beautiful boutique hotel in the Loop. The bar directly overlooks Grant Park, giving you stunning views of the park, downtown Chicago, and Lake Michigan. 

You can order craft cocktails, classic drinks, and food at Cindy’s. The offerings are good, but just know that they’re pricey. This place always books up, so be sure to make reservations in advance, if possible. Although, they do accept walk-ins. Overall, Cindy’s is an amazing spot for a date night or a special occasion.

Qing Xiang Yuan Dumplings

The best dumpling spot in Chicago (in my opinion, at least).

📍 Google Maps | Phone: (312) 799-1118 | Website | Hours: 11:30 am – 9 pm daily 

I’m a sucker for good dumplings. And in my opinion, no place in Chicago does it as good as Qing Xiang Yuan Dumplings (QXY) in Chinatown. I’ve eaten here countless times and each visit, the dumplings are fresh and freaking delicious. 

They don’t take reservations and there’s usually a bit of a wait, but trust me, it’s worth it. I recommend putting your name down and wandering around Chinatown while you wait. Once you’re in, order ones with different fillings to share with your group. I love the pan-fried pork and chive dumplings. Yum!

The Violet Hour

This speakeasy-type bar with unique and creative cocktails is nestled in the heart of Wicker Park.

📍 Google Maps | Phone: (773) 252-1500 | Website | Hours: 5 pm – 1 am daily 

The Violet Hour is one of Chicago’s best speakeasy bars. It’s located in the heart of Wicker Park and is “hidden” behind a mural wall. 

The Violet Hour has a moody and intimate atmosphere, which makes it a great spot for a date night or catching up with close friends. The menu has an awesome selection of craft cocktails with unique flavor combinations. Be sure to check out the seasonal menu, too. 

The drinks at Violet Hour are always tasty and the bartenders are knowledgeable and friendly. You can grab some small bites here as well.

Cool & Unusual

Kayak the Chicago River

Paddle down the Chicago River and take in the city from a new perspective.

📍 Google Maps | Phone: (312) 965-0035 | Urban Kayaks Website | Hours: departure times vary | Entrance: $60 single kayak, $120 tandem kayak | 👉 Book a Chicago River Kayak Tour

If you plan on visiting during the warmer months, try something a little different: kayak down the Chicago River! This is a fun activity for visitors of all ages and a unique way to experience the downtown scene. 

This Chicago River kayak tour is particularly popular. You get a history tour while you paddle along the urban landscape. Tours typically last about two hours and are beginner-friendly. 

Rent a Boat

Enjoy a leisurely boat ride at your own pace down the Chicago River.

📍 Google Maps | Phone: (312) 644-6411 | Website | Hours: 12 pm – 6 pm daily | Cost: Varies

It’s no secret that you can boat along Chicago’s waterways. But to go a little more off the beaten path, rent a boat through Chicago Boat Company. 

My friends and I rented a donut boat during the summer. The branch of the Chicago River we floated down was calmer, which was a nice change of pace from the city’s bustle. We brought our own drinks and snacks while my friend steered our boat. I highly recommend this if you’re looking for something unique during the warmer months!

You can book a Rockwell donut boat like I did through Chicago Boat Company. But if you’re visiting during the winter, you can still participate by renting something like a hot tub boat.

Candle Making Class at Edgewater Candles

Craft your own one-of-a-kind (and non-toxic) candle at this cozy and adorable local shop on Chicago’s north side.

📍 Google Maps | Website | Hours: 11 am – 6 pm daily | Cost: $60 per person (class, shop is free to enter) | 👉 Book a Candle Making Class

It’s a refreshing thing to talk to people who are truly passionate about what they do, and that’s exactly the vibe I got when I took a candle making class at Edgewater Candles. The owner, Mark, is fun, knowledgeable, and super passionate about all things candles! This makes taking a class engaging but also really informative. 

Candle making classes are done in small groups and last about two hours long. You can pick up to four scents to mix, and you walk away with two 6-oz candles. For my candles, I mixed chamomile-calamansi, palo santo, and aspen-fern, which turned out wonderfully!

Whether you’re a local or simply visiting Chicago, this is an awesome activity to try. Not to mention, a custom candle is a pretty cool souvenir to take home.

Restoration Hardware Chicago

Treat yourself to a fancy meal, then browse three floors of beautiful furniture showrooms.

📍 Google Maps | Phone: (312) 475-9116 | Website | Hours: 10 am – 8 pm Mon-Thu, 10 am – 9 pm Fri & Sat, 10 am – 7 pm Sun 

Check out Restoration Hardware Chicago (RH) if you’re a local who wants to wow visitors, or you’re a visitor yourself looking for something unique. This isn’t just a furniture showroom. RH is also home to the 3 Arts Club Cafe which is set in a beautiful atrium (see photo above). It’s the perfect spot to enjoy a little luxury and an activity all in one. 

Be sure to make a reservation at the cafe. After your meal, take your wine or coffee with you as you peruse the three floors of swanky showrooms. 

McDonald’s Global Headquarters

A McDonald’s in the West Loop that serves up menu items from around the world.

📍 Google Maps | Phone: (312) 291-9224 | Website | Hours: 5 am – 10 pm daily 

I know it seems odd to list McDonald’s among Chicago’s top attractions, but hear me out. “Global McDonald’s,” as most people call it, has a bonus international menu. This “Global Favorites” menu includes McDonald’s items from around the world. 

The menu isn’t extensive, but it’s a fun way to try something different. For example, you can try sweet potato fries from the Netherlands or an ebi filet-O from Japan. Find this McDonald’s global headquarters restaurant in the West Loop neighborhood.

Snakes & Lattes

This game cafe in Logan Square makes for the perfect winter or rainy day activity with friends.

📍 Google Maps | Phone: (872) 310-3999 | Website | Hours: 5 pm – 10 pm Mon-Thu, 5 pm – 11 pm Fri, 12 pm – 11 pm Sat, 12 pm – 9 pm Sun | Entrance: $7 adults

Whether you catch a rainy day or you’re visiting during the winter, there’s a good chance you’ll need an indoor activity to escape the elements. Plus, you can only visit so many museums before your feet get tired and you need to recharge. When that happens, make a reservation at Snakes & Lattes in Logan Square. 

This game cafe is the perfect spot to recharge while still having some fun. Plus, they serve food and drinks, so you’ll be covered in that department, too. My friends and I love to come here on rainy days when there’s nothing else to do. And with endless games available, you’re sure to stay entertained.

AIRE Ancient Baths Chicago

Find a little zen in bustling Chicago at this intimate, luxury spa that offers bath treatments and massages. 

📍 Google Maps | Phone: (312) 312-9610 | Website | Hours: 8 am – 11 pm daily | Cost: $200+

AIRE Ancient Baths is a luxurious spa in Chicago’s River West area. This spa isn’t your ordinary one. Instead, it’s housed in a restored factory and designed to feel like an ancient traditional bathhouse. 

This spa is luxurious and best known for its many pools, which include thermal baths and pools of different temperatures. You can also book massages and spa experiences for couples. Just note that the prices match the luxurious services. Booking a spa experience at AIRE is ideal for special occasions.

Renegade Craft Fair

This fun, colorful craft fair comes to Chicago multiple times a year. It’s the perfect place to shop the city’s creative makers all in one place.

📍 Location Varies | Website | Entrance: $5 suggested donation 

The Renegade Craft Fair is a weekend-long craft festival that comes to Chicago about four times a year. Dozens of local makers have booths selling everything from jewelry and pottery to skincare. It’s the perfect place to shop for unique goodies while also checking out a new area, since each festival takes place in a different neighborhood of Chicago. 

This is one of my all-time favorite events in Chicago. I almost always walk away with some cool new trinket or a unique gift for a loved one. Some examples: pasta-shaped ornaments, hand-drawn illustrations, perfume rollerballs, and so much more.

If this sounds like your vibe, be sure to check the festival dates. You might just catch one during your visit to the Windy City!

Chicago River Brunch Cruise

Brunch along the Chicago River and enjoy bottomless mimosas as the cityscape passes by.

📍 Google Maps | Website | Tickets: from $100+ adults | 👉 Premier Chicago River Brunch Cruise

A Chicago River brunch cruise floats you through the heart of the city while you enjoy a 3-course brunch and bottomless mimosas. Brunch lasts a couple of hours. 

The best part of a Chicago brunch cruise is the ambiance. The city skyline towers above guests and you’ll take in beautiful views with occasional narration of the iconic landmarks. It’s a great idea for a brunch date with your significant other, or celebrating a special occasion with loved ones. 

Hidden Gems

Myopic Books

One of Chicago’s largest used bookstores in the heart of Wicker Park.

📍 Google Maps | Phone: (773) 862-4882 | Website | Hours: 12 pm – 8 pm daily | Entrance: Free

Myopic Books is one of Chicago’s largest used bookstores. It’s located in the heart of Wicker Park and is the perfect place to wander if you’re a book lover. 

You’ll find three floors packed with floor-to-ceiling shelves of used books. Genres range from coffee table art books to classic novels and everything in between. 

The cozy but buzzing ambiance is what makes Myopic such a cool bookstore to visit. It’s a great spot to come with friends, alone, or even on a date. Each time my parents are in town, they always want to visit Myopic Books.

Dorian’s

Beyond the walls of this tiny record shop lies a cozy speakeasy and music venue.

📍 Google Maps | Phone: (773) 687-9824 | Website | Hours: 6 pm – 1 am Tue-Sun, Closed Mon | Entrance: $10+ cover

Dorian’s is an intimate speakeasy-like bar and music venue tucked in the heart of Wicker Park. Come here for a cozy date night or to listen to some talented musicians play. The venue is small, so arrive early if you plan on coming for the live music. The drink menu has plenty of tasty, unique options and the vibes are moody in the best way.

Poetry Foundation

A peaceful library and cultural center in River North that’s solely dedicated to poetry.

📍 Google Maps | Phone: (312) 787-7070 | Website | Hours: 11 am – 5 pm Wed-Sat, Closed Sun – Tue | Entrance: Free 

The Poetry Foundation is a poetry library and cultural center in River North. This hidden gem is for anyone who loves poetry, books, or anything literary. The best part? It’s totally free to visit. 

The library at the Poetry Foundation contains over 30,000 volumes of poetry and the shelves are packed from the floor to the ceiling. The atmosphere is serene and quiet, so it’s the perfect place to read or write. I think this is one of the coolest hidden spots in downtown Chicago.

Milton Lee Olive Park

An easily accessible downtown park that offers picture perfect skyline views.

📍 Google Maps | Phone: (312) 744-6635 | Website | Hours: 7 am – 8 pm daily | Entrance: Free 

Milton Lee Olive Park isn’t necessarily a “hidden gem” to locals. But, if you’re visiting Chicago for the first time, this is a fantastic spot to capture that perfect skyline shot. 

The small park is located adjacent to Navy Pier and can be easily accessed via the Lakefront Trail. It has plenty of grassy patches to lay out on for a picnic or simply to soak up a little sun. 

But the absolute best part of the park? The view. Here, you’ll enjoy beautiful, unobstructed skyline views along the lakeshore.

Promontory Point

Relax and picnic at this small and scenic Lake Michigan outcrop near Hyde Park.

📍 Google Maps | Phone: (773) 256-0159 | Website | Hours: 6 am – 11 pm daily | Entrance: Free 

Promontory Point is a small park well-loved by locals who know about it. This outcrop of green space is located near Hyde Park on Chicago’s South Side. 

The park juts out onto Lake Michigan and provides beautiful distant views of the Chicago skyline. There are bonfire pits for barbecuing and plenty of grass to spread out and enjoy a picnic with friends or family. Maybe set up a hammock or take a peaceful stroll by the water, since it connects with the Lakefront Trail.

Winter Garden at Harold Washington Library Center

A quiet winter “garden” and sitting area on the top floor of a massive downtown library.

📍 Google Maps | Phone: (312) 747-4300 | Website | Hours: 9 am – 8 pm Mon – Thu, 9 am – 5 pm Fri & Sat, 1 pm -5 pm Sun

Chicago’s Harold Washington Library Center is one of the largest public libraries in the world. The building itself takes up an entire city block! It’s hard to miss with its unique Postmodern architecture. The brick structure is capped with a green-hued steel cornice. Intricate sculptures appear on each corner, featuring owls that represent wisdom. 

The Winter Garden appears on the 9th floor. Its atmosphere is quiet and peaceful, so it’s perfect for reading a book or doing a little work on a rainy day. There’s also a small museum you can walk through, which is all about the history and legacy of Chicago’s first African-American mayor, Harold Washington.

Graceland Cemetery

Many notable Chicagoans are buried at this large, historic, and beautiful cemetery in Uptown Chicago. 

📍 Google Maps | Phone: (773) 525-1105 | Website | Hours: 8 am – 6 pm Mon – Fri, 9 am – 4 pm Sat & Sun | Entrance: Free 

Graceland Cemetery isn’t on most Chicago tourists’ lists, but it’s a unique and peaceful place. This large cemetery is located on Chicago’s North Side in the Uptown neighborhood. 

So much Chicago history lives on here, despite it being a place for those who have passed on. Prominent Chicagoans from government, sports, architecture, philanthropy, and so many other areas of life are buried here. 

The cemetery’s landscape and architecturally unique monuments and mausoleums are another thing that makes Graceland Cemetery beautiful. Stop in the Graceland Cemetery office to grab a map and take a self-guided tour.

The Honeycomb Pavilion

A striking sculptural pavilion in Lincoln Park, perfect for snapping photos.

📍 Google Maps | Entrance: Free

To Chicago locals, The Honeycomb is by no means a hidden gem; it’s just a fixture of Lincoln Park. However, if you’re new to the city, make a stop while you’re out exploring the park. It’s a great photo op that’s just off the South Pond boardwalk, right by the Lincoln Park Zoo.

Note that this is a popular spot for photoshoots, engagements, and even weddings. So, be mindful if there’s a private or special event taking place.

Chicago Entertainment & Nightlife

The Second City

Laugh your heart out at one of Chicago’s best comedy clubs.

📍 Google Maps | Phone: (312) 337-3992 | Second City Website | Hours: Showtimes vary | Entrance: $25+ 

Second City Comedy Club in Old Town has a long history and influence that’s made waves throughout the comedy world. Famous comedians like Joan Rivers, Bill Murray, Mike Meyers, Tina Fey, Amy Poehler, and so many others have performed and debuted here.   

If you’re someone who enjoys live shows (or frankly, just having a good time), snag a ticket to Second City. Shows can range from sketches and improv to stand-up and open mic nights. Your experience is sure to be memorable. After all, they say laughter is the best medicine.  

Note that the Second City has an age requirement. Only those 13+ will be admitted, although ages 13-17 will need adult accompaniment. Additionally, the club serves food & drinks. 

👉 Pro Tip: Bring a jacket with you! I don’t know why, but every time I’ve been to a show here, the room is always chilly.

United Center

Watch Chicago basketball, hockey, and more.

📍 Google Maps | Phone: (312) 455-4500 | United Center Website | Hours: Game and show times may vary, doors open 90 minutes prior to games | Entrance: Each event may vary 

On the Near West Side of Chicago is the city’s other famous sports venue: United Center. 

This indoor arena is home to the NBA’s Chicago Bulls and NHL’s Chicago Blackhawks. In addition to being a sports venue for basketball and hockey games, United Center serves as an arena for concerts and other shows.

If you go, check out the 58 banners hanging from the ceiling (marking championship titles for both the Bulls and the Blackhawks) and the 12-foot tall bronze Michael Jordan statue.

🛏️ Need a Hotel? The Hyatt House Chicago Medical/University District has good amenities and is located close to the arena if you’re going to an event at the United Center.

Chicago Theatre District

Witness world-class theatre and music concerts in downtown Chicago.

📍 Google Maps | Theatre District Website | Hours: Showtimes vary | Entrance: $25+

In the northern part of the Loop is the Chicago Theatre District. Here, you’ll find a wide array of theatres and performance venues. One of the major ones? The Chicago Theatre. This theatre, which primarily serves as a music and comedy venue, is widely known for its iconic red and gold marquee sign. 

A few other big theatres in the district include CIBC Theatre, James M. Nederlander Theatre, and Cadillac Palace Theatre. Each of these venues hosts exciting Broadway and non-Broadway productions. Either way, Chicago holds its own when it comes to a flourishing theatrical scene. 

👉 Looking for shows? For a more comprehensive list of theatres and independent venues, check out the website link above. 

Joffrey Ballet at Lyric Opera House

Get dressed up and treat yourself to an evening of ballet at a beautiful and historic opera house theater.

📍 Google Maps | Website | Hours: Showtimes Vary | Tickets: $36-$200

Treat yourself to a fancy night out by nabbing tickets to see the Joffrey Ballet perform at the Lyric Opera House. The Joffrey Ballet is one of the most renowned ballet companies in the country. They perform a mix of contemporary and classical repertoire. As someone with a ballet background, I can assure you they’re worth seeing. 

They perform at the Lyric Opera House in the Loop, which is a historic Art Nouveau and Art Deco-style theater. The architecture is stunning from the lobby to the theater itself, featuring opulent red and gold detailing. 

Make a night out of seeing the Joffrey Ballet by making reservations at a nice restaurant in the Loop or River North. Head to the ballet right after!

Buddy Guy’s Legends

Step into the heart of Chicago blues at this legendary venue.

📍 Google Maps | Phone: (312) 427-1190 | Buddy Guy’s Legends Website | Hours: 5 pm – 12 am Wed-Thu, & Sun, 5 pm – 12:30 am Fri, 5 pm -1:30 am Sat, Closed Mon, Tue | Entrance: $15+ each show may vary

If you’re a fan of classic American blues, then visiting Buddy Guy’s famous Legends Blues Club is a must. Since its opening by Buddy Guy in the summer of 1989, this music venue has become a Chicago music institution and is one of the world’s premier blues clubs. 

The Legends’ stage has been played by iconic musicians like the Rolling Stones, Eric Clapton, David Bowie, John Mayer, and more. If you’re at all interested in music and Chicago’s music history, then attending a show here is sure to be a Chicago highlight. 

Who knows, you might be lucky and get a surprise performance from Buddy Guy.  

Symphony Center

Listen to one of the best orchestras in the world.

📍 Google Maps | Phone: (312) 294-3000 | Chicago Symphony Orchestra Website | Hours: Showtimes vary | Entrance: Ranging from $30 – $300 

The Symphony Center is located in the heart of the Loop and is a great itinerary addition if you’re a classical music lover.

The Chicago Symphony Orchestra, which is world-renowned, performs here throughout the year in a range of styles. You can expect classical performances as well as contemporary ones. 

The Symphony Center also offers music series to engage younger audiences. Kid-friendly programs are available as well as movie-inspired musical performances. In addition, the Symphony Center welcomes pianists, jazz artists, and performers of world and folk music.

👉 Are you a new Chicago resident? Check out my ultimate Chicago cheat sheet. You’ll find everything from an overview of neighborhoods to where to make friends and plenty more.

Need a Hotel in Chicago? Search Our Top Picks Now

Just enter your dates in our hotel finder and discover the best reviewed hotels in Chicago:

Destination

Dates

Rating

All 7+ 8+ 9+

Number of Guests

Search

Results provided via our partner Booking.com. See our Advertising policy.

You can also read my guide to where to stay in Chicago for pros and cons of the best areas to stay.

Want More? Listen to My Chicago Podcast Episode!

If you liked this post, you’ll love my Chicago episode on the Travel Lemming Podcast. It’s available on YouTube, Apple Podcasts, Spotify, or wherever you get your podcasts (just search “Travel Lemming Chicago”). 

I talk about the best things to do in Chicago at minute mark 05:40.

The host, Betty, and I also discussed where to stay in Chicago (09:53), public transit & getting around Chicago (16:54), Chicago travel tips and nightlife (25:24), why more people should visit Chicago (01:50) and all the other common questions about travel to Chicago.

Download now and remember to listen to the entire episode before you arrive in Chicago.

***

The Windy City has so much to offer, and I really believe there’s something for everyone. Have you tried any of these Chicago activities? Tell us which ones were your favorites in the comments down below.

Next up, check out my ultimate Chicago itinerary for more trip-planning help.