Lea Rose Allbaugh is a freelance writer from the Blue Ridge Mountains of North Carolina. She’s currently based in Chicago (except for when she’s on a traveling stint), and is obsessed with all things travel. She caught the travel bug back in 2015 during an exchange to the Netherlands, and has been traveling ever since. Through her writing, she hopes to inspire others to get up and go experience the world. Aside from travel, she loves reading, writing, and anything creative. She writes on her website Written World.

Why We Love Chicago: Chicago is known for a lot of things: the Bean, deep-dish pizza, sports, and so much more. These things are all iconic to the city, but the Windy City has so much more to offer. For being one of the biggest cities in America, Chicago doesn’t feel overwhelming. The people are welcoming, there are tons of unique neighborhoods to explore, and visitors and locals alike will find that there’s always something to do. Not to mention, with Lake Michigan nearby and incredible architecture all around, there’s something to admire at every turn.

Best of Chicago

✨ Things to Do

View of people and the Bean in Millennium Park — *The Bean in Millennium Park on a clear day*

Chicago has no shortage of things to do for all ages and interests. These are my top recommendations:

Millennium Park – This is where you’ll find the Bean! It’s close to other attractions and a great spot for city views.
The Art Institute – Chicago’s premier art museum with an impressive & diverse collection.
Chicago Riverwalk – A central place to explore, sightsee, and take some great pictures.
Lake Michigan Beaches – Enjoy swimming, city views, and other activities at Chicago’s beaches.
Lakefront Trail – This 18-mile trail hugs the Lake Michigan shoreline and offers city views.
Explore Neighborhoods – Chicago is home to diverse and unique neighborhoods. Explore off the beaten path.
Eat & Drink – Chicago has just about every cuisine imaginable. Try something new and enjoy a tasty meal.

👉 Explore all things to do in Chicago.

🗺️ Where to Stay

Depending on why you’re visiting Chicago, the neighborhood you choose to stay in may vary. But generally, these are the best and most central neighborhoods:

The Loop – The center of downtown Chicago. Close proximity to museums, attractions, restaurants, and shopping.
River North – Close to the Magnificent Mile and Riverwalk. Upscale area with fine dining and nightlife.
West Loop – A great place for foodies. Upscale restaurants, casual eats, and local joints all around.
Lincoln Park – Family-friendly area with ample greenspace, lake access, shops, and restaurants.
Wicker Park – Younger crowds will love the thrift stores, music venues, bars, and cafes here.

👉 Read the complete guide to where to stay in Chicago.

The author looking at the Chicago River — *Travel Lemming writer, Lea Rose, at the Chicago River between the Loop and River North*

🛎️ Best Hotels

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View of Wacker Drive entrance to London House in Chicago — **LondonHouse Chicago** (photo: James.Pintar / Shutterstock.com)

Chicago is filled with hotels to suit everyone’s needs and preferences. Below are my top picks, depending on what you’re looking for:

LondonHouse Chicago – A modern, luxurious hotel in the heart of downtown Chicago along the river.
Chicago Athletic Association – A unique boutique hotel with a rooftop bar across the street from Millennium Park.
The Publishing House Bed and Breakfast – A beautifully designed boutique hotel with great hospitality in the West Loop.
Freehand Chicago – A family-friendly and budget-friendly hotel in River North.
The Langham Chicago – An ultra-luxurious hotel on the Chicago River with tons of amenities.

🍽️ Restaurants

You’ll find some incredible food in Chicago. No matter your taste buds or budget, you’ll be able to find something delicious:

Time Out Market – Trendy food hall with restaurant vendors from all over Chicago. Located in West Loop.
Girl & The Goat – This West Loop restaurant serves delicious New American cuisine. Good for special occasions.
Lou Malnati’s – Stop here for your classic deep-dish pizza. Locations all over Chicago.
Kasama – A modern Filipino restaurant & bakery with a Michelin star in Ukrainian Village. Expect long lines.
Bang Bang Pie & Biscuits – A local pie shop and hidden gem in Logan Square. A personal favorite.

👉 Read the full list of 43 best restaurants in Chicago.

A food starter of Naan and dip, and sauteed green beans of Girl and the Goat — *Girl & The Goat*

🚗 Day Trips

Overlooking view of buildings in Downtown Milwaukee — *Views of downtown, Milwaukee*

Milwaukee, WI – A smaller city with a great downtown area, river and lake access, and hopping beer scene.
Holland, MI – A charming small town with a Dutch twist. See canals, windmills, tulips, and more. Fun for the whole family.
Michigan City, IN – A small lakeside city that’s close to Indiana Dunes National Park and other small towns.
Oak Park, IL – Enjoy arts and culture, and a visit to the Frank Lloyd Wright Home & Studio.
Lake Geneva, IL – A resort town with a rich architectural history, friendly downtown, and tons of outdoor activities.

👉 Read the complete guide on day trips from Chicago.

🏘️ Neighborhoods

Cars and establishments in Downtown Wicker Park — *“Downtown” Wicker Park*

Lincoln Park – Charming residential streets, great shopping and dining, and close to the park and zoo.
West Loop – An upscale, yet industrial vibe. West Loop is home to Fulton Market district, which is Chicago’s foodie area.
Wicker Park – An artsy neighborhood with lots of cool, local shops, venues, cafes, and more.
Gold Coast – An architectural gem with historic homes and buildings, only a short walk to Lake Michigan.
Hyde Park – A historically rich neighborhood on the South Side home to museums and the University of Chicago.

👉 Read the full list of 19 best Chicago neighborhoods.

🍸 Bars

People dining at Cindy's Rooftop Restaurant at Chicago Athletic Association Hotel — *Cindy’s Rooftop*

Howl at the Moon – Energetic bar in River North that’s great for live music, singing, and dancing.
Cindy’s Rooftop – Stylish rooftop bar in the heart of the Loop. Great ambiance, specialty cocktails, and beautiful city views.
Fadó – (Pronounced F’doe) An Irish pub great for sports fans and beer lovers. Located in River North.
Roscoe’s Tavern – LGBTQ bar in Lakeview. Fun and lively atmosphere with drink specials, events, and an outdoor patio.

🏛️ Best Chicago Museums

A lion statue on the entrance of The Art Institute — *Entrance to the Art Institute*

The Art Institute – Witness artwork from around the world and throughout history at this huge downtown museum.
Museum of Contemporary Art Chicago – This Streeterville museum features thought-provoking pieces & rotating exhibits.
Museum Campus – A 57-acre park that includes the Field Museum, Shedd Aquarium, and Adler Planetarium.
Chicago History Museum – Learn all about Chicago’s story and history with permanent and rotating exhibits.
Chicago Children’s Museum – Located on Navy Pier, this is an educational and immersive museum just for kids.

👉 Read the full list of 20 best museums in Chicago.

🆓 Best Free Activities

Statue of Bears on top of the Lincoln Park Zoo sign — *Lincoln Park Zoo*

Lincoln Park Zoo – This 35-acre zoo has a variety of wildlife exhibits and some interactive animal experiences.
Chicago Cultural Center – A cultural and historical hub known for its free arts events and two stained-glass domes.
Garfield Park Conservatory – The largest conservatory in America with extensive outdoor landscapes and greenhouses.
Lincoln Park Conservatory – A vibrant greenhouse and botanical garden located in Lincoln Park.
Harold Washington Library Center – Chicago’s public library has over a million books, beautiful architecture, and a winter garden.

👉 Read the full list of 18 free things to do in Chicago

🌳 Best Outdoor Attractions

The author, Lea Rose Allbaugh kayaking at the Chicago River — *Lea Rose kayaking the Chicago River*

Riverwalk – A 1.25-mile walking trail through the center of the city and along the Chicago River.
Lakefront Trail – 18 miles of coastline with incredible city and lake views. Perfect for walking, running, and biking.
The “606” – An elevated, urban greenspace that goes for 2.7 miles and connects different neighborhoods.
Lincoln Park – Over 1,000 acres of park that runs along the lakefront, close to several Chicago beaches.
Grant Park – 300 acres of green space, and arts and culture attractions in the downtown Loop.

🏙️ Best Attractions for Architecture

The author Lea Rose Allbaugh, posing for a photo on the Chicago river cruise with the tall buildings in the background — *Lea Rose on an architecture cruise*

Architecture Cruise – A great way to sightsee and learn about Chicago’s history and architecture.
THE MART – Also known as the Merchandise Mart, this historical landmark was once the biggest building in the world.
Frank Lloyd Wright Home & Studio – Located in Oak Park, this is the home and studio of American architect, Frank Lloyd Wright.
Rookery Building – A late 19th-century skyscraper with iconic features, architectural details, and rich history.
Robie House – A distinctly American, prairie-style home designed by Frank Lloyd Wright, located in Hyde Park.

Chicago Travel Advice

🗓️ Best Time to Visit

Chicago has very cold winters and really hot summers. In spring and fall, the weather can flip-flop from hot to cold.

🌞 Summer – My favorite season in Chicago. Days are hot, but the city is buzzing and the lake is refreshing.
🍂 Fall – Cool, pleasant weather for walking and exploring. A good time to see fall foliage in the parks in Chicago.
🌼 Spring – Cool, but sunnier days where you’ll still need a jacket or coat. Unpredictable weather.
❄️ Winter – The weather is cold and it snows often. Dressing in layers is essential.

🗓️ See the full guide to the best time to visit Chicago.

🚌 Getting Around

Chicago is fairly easy to navigate. Public transportation is convenient, and you can cover a lot of ground just by walking.

🚶‍♀️ Walking – Chicago is a very walkable city as long as you plan on staying within a few neighborhoods.
🚗 Driving – Chicago is driveable, but parking can be difficult and pricey. See our full guide to driving in Chicago for tips.
🚇 Public Transit – Generally the best way to get around. The CTA operates trains (The “L”) and buses throughout the city.
📲 Ride Share – Ubers and Lyfts are almost always available. Prices can vary based on time and location.
🚴‍♀️ Biking – Chicago is bike-friendly. There are bike lanes and Divvy rentals throughout the city.
🛴 Scooters – Electric scooters are available in Chicago, but not allowed on the 606 and Lakefront trails.

👉 Read our full guide to getting around Chicago.

👉 Tips & Things to Know

🚇 – Ventra Card – You’ll need this for public transit. You can buy one online, at any train stop, or various shops.
🎉 – Be Mindful of Events – Festivals and events happen all year long, but especially in summer. Plan accordingly.
🍽️ – Reservations – Reservations are a good idea to avoid disappointment and long wait times. Especially at popular spots.
💬 – Midwestern Hospitality – Don’t be afraid to say hello to people–Chicagoans are friendly.
🏡 – Neighborhoods – Chicago is full of charming and unique neighborhoods. Be sure to spend some time exploring them.
🌿 – Weed is Legal – Recreational marijuana is legal and sold in dispensaries in Illinois for those 21+.

👉 See the full list of Chicago travel tips.

🧳 What to Pack

🧥 – Layers – Weather can be unpredictable with the Lake effect. To be safe, dress in layers.
👟 – Good Walking Shoes – You’re likely to be on your feet all day, so having comfortable walking shoes is a must.
🥾- Waterproof boots – If you plan on visiting in the winter, pack boots or shoes that are waterproof with good grip.
🛍️ – Reusable Bags – A lot of places in Chicago charge a fee for plastic bags, so bring your own reusable ones instead.
👜 – Belt Bags – Lots of people in Chicago use belt bags as purses. It’s a good way to keep your items accessible and close to you.
🕶️ – Sunglasses – Shield your eyes from the sun, wind, and even bright snow.

👉 See the full list of Chicago packing list.

🤓 Facts & Info

Census Population (2024) – 2.721 million
Time Zone – Central Standard Time (UTC -6 / UTC -5 during daylight savings)
Area Codes – 312, 773, and 708
Airports – O’Hare International Airport (ORD), and Chicago Midway International Airport (MDW)
Nickname – the Windy City, Chi-Town, the Second City
Demonynm – Chicagoan
State – Illinois
Country – United States of America

👉 Read the full list of facts about Chicago.

💵 Costs & Budgeting

3 Star Hotel Room – $120-$300/night
1 Bedroom Apartment Rental – $100-$300/night
Rental Car – $100-$200/day
Public Transit Ticket – $5 day pass ($2.50 to airport from center)
Ride Share from Downtown to Airport – $40
Take Out Meal for Two – $40-$60
Sit Down Dinner for Two – $50-$75
Draft Beer – $8-$12

👉 See our full Chicago budget guide for more.

FAQs

Is Chicago safe for tourists?

Chicago is safe for tourists, however, like most big cities, Chicago has its fair share of crime. Being aware of your surroundings can go a long way. Keep personal items like purses and bags close to you, and exercise extra caution at night time. As far as neighborhoods go, as long as you stick to the downtown, populated areas, you should be fine.

When is the best time to visit Chicago?

Spring and fall are the most recommended times to visit Chicago. The weather is mild and great for exploring the city on foot. However, locals will tell you that summers in Chicago are unmatched. If you do plan on visiting in the summer, though, know that the city can get really crowded and hot.

How many days should I spend in Chicago?

3-5 days is the amount of time recommended for visitors. This should give you enough time to see the sights and visit major attractions. Chicago is a big city with a lot to offer, so how tightly you pack your itinerary depends on what you’re looking to do. For a more leisurely trip with some time to explore, five days should be enough.

Where should I stay in Chicago?

The Loop, or close to it, is where most visitors tend to stay. That being said, there are a lot of advantages to staying in other neighborhoods–prices may be lower, accommodations will be more low-key, and your experience is likely to be less “touristy.” The North side and Lincoln Park are good options.

Which airport should I fly into?

Chicago has two airports: O’Hare and Midway. Both are international airports and have train access into the city. Which airport you decide to fly into will depend on a few factors. O’Hare has a wider range of airlines that fly in and out of the airport, so you’re likely to have more flight options here. Midway is technically closer to the city distance-wise, but the airlines are limited.

Meet Our Chicago Travel Expert

Lea Rose Allbaugh

👉 Read Lea Rose’s Articles