Where to Stay in Chicago (13 Best Places, By a Local)
👉 Jump to: Best Places to Stay in Chicago | Neighborhoods & Areas | Tips | Podcast | FAQ
As a Chicago local, I’m here to help you decide where to stay.
If you’re a first-time visitor, the Loop is where you’ll want to be. Here, you’ll be within walking distance of top attractions like Millennium Park, Navy Pier, the Magnificent Mile, and the Art Institute. Plus, you’ll have easy access to the “L” (trains).
I recommend staying at LondonHouse Chicago because of its awesome location overlooking the Chicago River. Not to mention, it has family rooms and amenities like a spa, fitness center, and rooftop terrace. Looking for something a little more unique? The Chicago Athletic Association is a beautiful boutique hotel across from “the Bean” with a rooftop bar.
However, if you’re here for a repeat visit or prefer a more low-key vibe, check out the other neighborhoods in this article! Like Lincoln Park for families or Wicker Park for younger people. There’s a Chicago neighborhood for every trip, budget, and interest.
Keep reading for the full breakdown of where to stay!
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Best Places to Stay in Chicago
My top hotel recommendations 👇
- 🏆 Best Overall Hotel – LondonHouse Chicago
- 📍 Best Location – LondonHouse Chicago
- 💎 Best Luxury Hotel – The Langham Chicago
- 👪 Best for Families – Loews Chicago Hotel
- 💻 Best for Business – The Westin Chicago River North
- 🔔 Best Boutique – The Publishing House Bed and Breakfast
- 🏙️ Best Near Millennium Park – Chicago Athletic Association
- 🏨 Best Hostel – HI Chicago Hostel
- 🛏️ Best Budget – Freehand Chicago
Click here to see all top Chicago hotels or here for apartments.
Ok, let’s do a deep dive into the best areas and neighborhoods in Chicago:
13 Best Neighborhoods & Areas to Stay in Chicago
The center of downtown Chicago is known as “the Loop.” All train lines meet and form a “loop” in this part of the city, hence the name. The Chicago River and Lake Michigan border the Loop, and other neighborhoods are located around it.
Popular neighborhoods like River North, Gold Coast, and Lincoln Park are in the north. Areas like Wicker Park and West Loop fall to the west. Neighborhoods like South Loop and Hyde Park are to the south.
Chicago Loop
👉 Best Area For First-Time Visitors | ✨ Best Loop Hotels: LondonHouse Chicago • Chicago Athletic Association • Pendry Chicago • citizenM Chicago Downtown
The Chicago Loop is commonly referred to as “the Loop” by locals and is the heart of downtown Chicago. This is where all train lines meet or “loop,” giving the neighborhood its name. It’s the best area to stay if you’re a first-time visitor.
The Loop is where you’ll find top attractions like Millennium Park, Willis Tower Skydeck, and the Art Institute of Chicago. Staying here allows you to be central. You can easily reach other museums and landmarks, whether they’re north, west, or south. You’ll be in the middle of it all. Plus, the Loop is within walking distance of restaurants and shops, making it easy to explore night and day.
I recommend staying at the LondonHouse Chicago for its terrific location overlooking the Chicago River and overall value for its price and modern amenities. Plus, it has private parking available.
The Chicago Athletic Association is another beautiful hotel in the Loop with boutique decor and views of Millennium Park and Grant Park. Plus, it has a scenic rooftop bar called Cindy’s.
Pros of Staying in Chicago Loop Neighborhood:
- Central location
- Walkable
- Close to shops, restaurants, and top attractions
- Some of the best Chicago hotels are located here
- Accessible by Blue, Brown, Green, Orange, Pink, and Purple Lines
Cons of Staying in Chicago Loop Neighborhood:
- Noisy
- Crowded
- Expensive
- Touristy
📚 Chicago Loop Mini Guide 📚
Best Area to Stay for First-Time Visitors
Google Map
✨ Best Hotels – LondonHouse Chicago • Chicago Athletic Association • Pendry Chicago • citizenM Chicago Downtown
🏠 Apartments – Browse Top Rentals in Chicago Loop
🍽️ Where to Eat – The Dearborn ($$), Revival Food Hall ($$), Cafecito ($$)
🍸 Where to Drink – Cindy’s Rooftop, Miller’s Pub, Monk’s Pub
🎟️ Top Attractions – Grant Park, Millennium Park, Cloud Gate (“The Bean”), The Art Institute of Chicago, Skydeck Chicago at Willis Tower, Chicago Riverwalk, The Chicago Theatre
River North
👉 Best Area For Nightlife | ✨ Best River North Hotels: Freehand Chicago • The Westin Chicago River North • The Langham Chicago
River North is where to stay if you want to be close to the city center and partake in some nightlife. I’d especially recommend River North to young professionals who want that vibrant city life feel. However, it’s a good area to stay for anyone new to the city.
River North is located just north of the Loop across the Chicago River. This area is full of trendy restaurants, art galleries, bars, and clubs. You’ll be within easy walking distance of the Loop, Magnificent Mile, and other popular areas.
The Westin Chicago River North is an overall good hotel choice with a great location in River North. Freehand Chicago is ideal for families and those visiting on a budget. It offers family and bunk-style rooms.
Pros of Staying in River North Neighborhood:
- Central location
- Walkable
- Close to shops and restaurants
- Vibrant nightlife
- Close to the Chicago River
- Accessible by Brown, Purple, and Red Lines
Cons of Staying in River North Neighborhood:
- Noisy from nightlife
- Less local character
📚 River North Mini Guide 📚
Best Area to Stay for Nightlife
Google Map
✨ Best Hotels – Freehand Chicago • The Westin Chicago River North • The Langham Chicago
🏠 Apartments – Browse Top Rentals in River North
🍽️ Where to Eat – Pizzeria Portofino ($$), Etta ($$), avec ($$)
🍸 Where to Drink – The Green Door Tavern, Fadó Irish Pub, The Drifter, Arabella
🎟️ Top Attractions – Chicago Riverwalk, Magnificent Mile, The Richard H. Driehaus Museum, Museum of Ice Cream
Magnificent Mile
👉 Best Area For Shopping | ✨ Best Magnificent Mile Hotels: Park Hyatt Chicago • The Gwen, Michigan Avenue Chicago • The Drake Hotel
The Magnificent Mile is Chicago’s most famous shopping street, located on N Michigan Avenue. It’s sandwiched between River North and Streeterville, and a great area to stay if shopping is a priority.
You’ll find countless name-brand shops and landmarks here. Luxury shops include The RealReal, Saks Fifth Avenue, Louis Vuitton, and others. Places like the Starbucks Reserve Roastery and Water Tower Place Mall are here, too. Notable Chicago landmarks lie along the Magnificent Mile, including the Historic Water Tower and 875 North Michigan Ave (formerly John Hancock Center).
The downside to staying near the Magnificent Mile is that it tends to be more expensive since it’s a touristy area. Park Hyatt Chicago is an expensive hotel here, but it’s luxurious, has a great location, and views of Lake Michigan. The Drake Hotel is another option. This historic, classically-decorated hotel sits right up against Oak Street Beach.
Pros of Staying in Magnificent Mile Neighborhood:
- Great shopping
- Central location
- Walkable
- Close to Lake Michigan
- Accessible by the Red Line
Cons of Staying in Magnificent Mile Neighborhood:
- Can be pricey
- A bit touristy
📚 Magnificent Mile Mini Guide 📚
Best Area to Stay for Shopping
Google Map
✨ Best Hotels – Park Hyatt Chicago • The Gwen, Michigan Avenue Chicago • The Drake Hotel
🏠 Apartments – Browse Top Rentals in Magnificent Mile
🍽️ Where to Eat – Gibsons Bar & Steakhouse ($$$$), Billy Goat Tavern ($), Starbucks Reserve Roastery ($$)
🍸 Where to Drink – Billy Goat Tavern, Z Bar, Streeter’s Tavern
🎟️ Top Attractions – Shopping, 360 CHICAGO at the John Hancock Center, Museum of Contemporary Art, Chicago Water Tower, Navy Pier
Streeterville
👉 Best Downtown Area For Families | ✨ Best Streeterville Hotels: Loews Chicago Hotel • Embassy Suites by Hilton Chicago Downtown Magnificent Mile • Courtyard Chicago Downtown/Magnificent Mile
Streeterville is located just east of the Magnificent Mile. I recommend Streeterville to families who’d prefer to stay downtown. It’s closest to Navy Pier, which is a popular attraction for families, as it’s home to rides, the Chicago Children’s Museum, Chicago’s Funhouse Maze, and other activities.
Places like The LEGO Store Chicago, American Girl Place, the Museum of Ice Cream, and Maggie Daley Park are within walking distance of Streeterville. Other attractions like Millennium Park, 360 Chicago at the John Hancock Center, and the Museum of Contemporary Art are close, too.
Loews Chicago Hotel is a good choice for families and offers all the modern amenities you need. It’s even pet-friendly. Courtyard Chicago Downtown/Magnificent Mile is similarly good for families but a little more budget-friendly. However, all the hotels mentioned for Streeterville are highly rated and offer family rooms.
Pros of Staying in Streeterville Neighborhood:
- Central location
- Family-friendly attractions nearby
- Close to shopping and restaurants
- Accessible by the Red Line
Cons of Staying in Streeterville Neighborhood:
- Can be noisy from nearby nightlife and hospital
- Can be pricey
- Less local charm
📚 Streeterville Mini Guide 📚
Best Downtown Area to Stay for Families
Google Map
✨ Best Hotels – Loews Chicago Hotel • Embassy Suites by Hilton Chicago Downtown Magnificent Mile • Courtyard Chicago Downtown/Magnificent Mile
🏠 Apartments – Browse Top Rentals in Streeterville
🍽️ Where to Eat – Volare Ristorante Italiano ($$), Beatrix ($$), Gyu-Kaku Japanese BBQ ($$)
🍸 Where to Drink – Lizzie McNeill’s, Streeter’s Tavern, D4 Irish Pub & Cafe
🎟️ Top Attractions – Navy Pier, Museum of Contemporary Art, Oak Street Beach, 360 CHICAGO at the John Hancock Center, Museum of Ice Cream, Lakefront Trail
Lincoln Park
👉 Best Area For Families | ✨ Best Lincoln Park Hotels: Hotel Lincoln • Hotel Versey Days Inn by Wyndham Chicago • The Willows Hotel • The Neighborhood Hotel Lincoln Park
Lincoln Park is the best place to stay in Chicago for families. This North Side neighborhood is walkable, safe, and full of green space. Lincoln Park is also a nice choice for returning visitors who are familiar with the city and want a quieter, local vibe.
The neighborhood is full of brownstones and a variety of vacation rentals. Hotels are pretty limited, though, and Hotel Lincoln is the main choice if you want to be centrally located in the neighborhood. But this is what makes Lincoln Park quieter and less touristy. I also suggest The Neighborhood Hotel Lincoln Park for families who want apartment-style accommodations.
You’ll have easy access to attractions like the Lincoln Park Zoo, the Chicago History Museum, and North Avenue Beach if you stay here. There are great streets for walking around, plus cute shops and top-notch restaurants to try. Check out the area around W Armitage Avenue and N Halsted Street!
Pros of Staying in Lincoln Park Neighborhood:
- Walkable
- Local charm
- Lots of local shops and restaurants
- Great access to parks in Chicago
- One of Chicago’s safest areas
- Accessible by Brown, Purple, and Red Lines
Cons of Staying in Lincoln Park Neighborhood:
- Not the most convenient public transportation access
- Farther from downtown Chicago
- Limited hotel options
📚 Lincoln Park Mini Guide 📚
Best Area to Stay for Families
Google Map
✨ Best Hotels – Hotel Lincoln • Hotel Versey Days Inn by Wyndham Chicago • The Willows Hotel • The Neighborhood Hotel Lincoln Park
🏠 Apartments – Browse Top Rentals in Lincoln Park
🍽️ Where to Eat – Galit ($$$), Blue Door Farmstand ($$), Summer House Santa Monica ($$)
🍸 Where to Drink – The J. Parker, The Red Lion Pub, The Galway Arms
🎟️ Top Attractions – Lincoln Park, Lincoln Park Zoo, Lincoln Park Conservatory, Alfred Caldwell Lily Pool, Chicago History Museum, Peggy Notebaert Nature Museum, North Avenue Beach
West Loop
👉 Best Area For Foodies | ✨ Best West Loop Hotels: Nobu Hotel Chicago • The Publishing House Bed and Breakfast • The Hoxton, Chicago
The West Loop is the place to stay if you want to experience Chicago’s foodie scene. It’s one of the city’s trendiest neighborhoods and ideal if you’re visiting for an event at the United Center.
This neighborhood is located west of the Loop and is chock full of trendy, upscale restaurants and bars. You’ll find some of Chicago’s best restaurants, like Girl & The Goat and Au Cheval, along with Time Out Market. There are so many other amazing restaurants here, though.
The West Loop is home to stylish, unique hotels that match the neighborhood’s lively vibe.
Nobu Hotel is a modern luxury hotel with three restaurants (including a rooftop bar) right in the Fulton Market District. Nearby is The Hoxton, Chicago, a cozy yet chic hotel with a rooftop pool and three restaurants and bars, including a fun speakeasy called Lazy Bird. The Publishing House Bed and Breakfast is another highly-rated boutique hotel with a more relaxed atmosphere.
Pros of Staying in West Loop Neighborhood:
- World-class food scene
- Trendy and lively atmosphere
- Accessible by the Green & Pink Lines
Cons of Staying in West Loop Neighborhood:
- Can be pricey
- Limited hotel options
- Farther from top Chicago attractions
📚 West Loop Mini Guide 📚
Best Area to Stay for Foodies
Google Map
✨ Best Hotels – Nobu Hotel Chicago • The Publishing House Bed and Breakfast • The Hoxton, Chicago
🏠 Apartments – Browse Top Rentals in West Loop
🍽️ Where to Eat – Girl & The Goat ($$$), Au Cheval ($$$), Time Out Market Chicago ($$), J.P. Graziano Grocery ($)
🍸 Where to Drink – Lone Wolf, Blind Barber, Emporium Arcade Bar
🎟️ Top Attractions – Fulton Market District, Emporium Arcade Bar, AIRE Ancient Baths Chicago, French Market, United Center
Wicker Park
👉 Best Area For Young People | ✨ Best Wicker Park Hotels: The Robey • Wicker Park Inn • Hyatt Place Chicago Wicker Park
Wicker Park is a fantastic neighborhood for younger visitors who want a vibrant yet local atmosphere while still having easy train access to downtown Chicago.
Wicker Park is located northwest of the Loop. You’ll find tons of things to do in this neighborhood. It’s home to tons of cool restaurants, coffee shops, music venues, and vintage boutiques. The vibe here is buzzing but not too touristy. It’s a part of town that many locals love to visit and explore. There are also cute residential streets to wander down. I love the houses along Hoyne Ave.
I recommend staying at The Robey to be in the heart of Wicker Park. This hotel provides great views and a boutique atmosphere, plus a restaurant and rooftop bar. Wicker Park Inn is a good option for couples since it’s on a quieter residential street but is still close to everything.
Pros of Staying in Wicker Park Neighborhood:
- Local charm
- Lots of shops and restaurants to enjoy
- Vibrant but not too touristy
- Accessible by the Blue Line
Cons of Staying in Wicker Park Neighborhood:
- Farther from downtown Chicago
- Can be noisy
📚 Wicker Park Mini Guide 📚
Best Area to Stay for Young People
Google Map
✨ Best Hotels – The Robey • Wicker Park Inn • Hyatt Place Chicago Wicker Park
🏠 Apartments – Browse Top Rentals in Wicker Park
🍽️ Where to Eat – Big Star ($$), Bloom Plant Based Kitchen ($$), Amaru ($$)
🍸 Where to Drink – The Violet Hour, Estelle’s Cafe & Lounge, Dorian’s
🎟️ Top Attractions – Wicker Park Farmers Market, Myopic Books, Subterranean, Chop Shop, Vintage shopping, local coffee shops
Gold Coast
👉 Best Area For Luxury | ✨ Best Gold Coast Hotels: Viceroy Chicago • Thompson Chicago • Ambassador Chicago
Gold Coast is an affluent neighborhood in Chicago’s Near North Side. Stay here if you want luxury, peace, and quiet, but still want walkability to shops and restaurants.
Gold Coast is a mix of quiet residential streets and commercial shopping areas. You’ll find picturesque brownstones on tree-lined streets. Luxury stores like Giorgio Armani, Chanel, and Hermes can be found around Oak Street near the top of the Magnificent Mile.
On the other hand, Gold Coast has easy access to nature and scenery. The famous Lake Shore Drive hugs the eastern edge of Gold Coast. You can easily access Lake Michigan and Oak Street Beach from this neighborhood.
Viceroy Chicago is a luxurious hotel with beautiful rooms and attentive staff that’s right in the middle of shops and restaurants. It’s a great option for couples staying in Chicago. If you want quieter luxury, book a stay at Ambassador Chicago, which is on a residential street just a stone’s throw from the lake.
Pros of Staying in Gold Coast Neighborhood:
- Luxurious atmosphere
- Safe
- Centrally located
- Walkable
- Close to Lake Michigan
- Accessible by the Red Line
Cons of Staying in Gold Coast Neighborhood:
- More expensive
- Not much nightlife
📚 Gold Coast Mini Guide 📚
Best Area to Stay for Luxury
Google Map
✨ Best Hotels – Viceroy Chicago • Thompson Chicago • Ambassador Chicago
🏠 Apartments – Browse Top Rentals in Gold Coast
🍽️ Where to Eat – Gibsons Bar & Steakhouse ($$$$), Velvet Taco ($$), 3 Arts Club Cafe ($$)
🍸 Where to Drink – 3 Arts Club Cafe, Sparrow
🎟️ Top Attractions – Oak Street Beach, Lakefront Trail, International Museum of Surgical Science, Original Playboy Mansion, Charnley-Persky House Museum
Old Town
👉 Best Area For Comedy Shows & Convenience | ✨ Best Old Town Hotels: Hotel Lincoln • Claridge House • The Sono Chicago
Old Town is a great area for a couple of reasons. Firstly, it’s home to top-notch comedy venues. The iconic Second City Comedy Club is located in the heart of the neighborhood. You’ll also find local comedy spots like Zanies and BATSU! Chicago. And, you can easily hop on a bus or rideshare to reach more comedy clubs in nearby Wicker Park.
Secondly, Old Town is conveniently located at the crossroads of popular places. Lincoln Park (neighborhood and park), North Avenue Beach, and the Lakefront Trail are within short walking distance. Downtown areas like the Loop, River North, and Magnificent Mile are easy to reach, too.
There aren’t many hotels in Old Town, but there is Hotel Lincoln. This hotel has an awesome location overlooking Lincoln Park and it’s right near the heart of Old Town. I also recommend looking into vacation rentals for your stay.
Pros of Staying in Old Town Neighborhood:
- Very walkable
- Convenient location
- Close to other popular areas
- Plenty of bars and restaurants to choose from
- Great area for comedy clubs
Cons of Staying in Old Town Neighborhood:
- Limited hotel options
📚 Old Town Mini Guide 📚
Best Area to Stay for Comedy Shows & Convenience
Google Map
✨ Best Hotels – Hotel Lincoln • Claridge House • The Sono Chicago
🏠 Apartments – Browse Top Rentals in Old Town
🍽️ Where to Eat – Evette’s Lincoln Park ($$), Topo Gigio Ristorante ($$), Nookies on Wells ($$), Small Cheval – Old Town ($$)
🍸 Where to Drink – Old Town Ale House, Marge’s Still, Corcoran’s Grill & Pub
🎟️ Top Attractions – The Second City Comedy Club, Zanies Comedy Night Club, Chicago History Museum, Lincoln Park, Lincoln Park Zoo, Lakefront Trail
South Loop
👉 Best Area For Museums & Stadium Events | ✨ Best South Loop Hotels: Homewood Suites • The Blackstone, Autograph Collection • Hilton Chicago
South Loop is located where it sounds: south of the Loop. Stay here if visiting museums is a top priority, or if you’re in town for an event at Soldier Field.
The South Loop is home to Chicago’s lakefront Museum Campus. Here, you’ll find the Shedd Aquarium, the Field Museum, and Adler Planetarium. The South Loop also puts you near the southern edge of Grant Park. So, you can easily access the Art Institute and Millennium Park.
Soldier Field is located in the South Loop and is the home to the Chicago Bears football team. Many stadium concerts are held here, too. Homewood Suites is a great hotel choice for its proximity to Museum Campus and Soldier Field.
Pros of Staying in South Loop Neighborhood:
- Close to popular Chicago museums and Soldier Field
- Accessible by the Red, Orange, and Green Lines
- Close to downtown Chicago
Cons of Staying in South Loop Neighborhood:
- Not as walkable as other neighborhoods
- More limited hotel options
📚 South Loop Mini Guide 📚
Best Area to Stay for Museums & Stadium Events
Google Map
✨ Best Hotels – Homewood Suites • The Blackstone, Autograph Collection • Hilton Chicago
🏠 Apartments – Browse Top Rentals in South Loop
🍽️ Where to Eat – Eleven City Diner ($$), Lowcountry South Loop ($$), Flo & Santos ($$)
🍸 Where to Drink – Kasey’s Tavern, First Draft, Reggies Chicago
🎟️ Top Attractions – Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field, Buddy Guy’s Legends, Northerly Island Park, 12th Street Beach, Printer’s Row
Hyde Park
👉 Best Area For History & Culture | ✨ Best Hyde Park Hotels: Sophy Hyde Park • Hyatt Place Chicago-South/University Medical Center • The Study at the University of Chicago
Hyde Park is a historic neighborhood on Chicago’s South Side. I recommend Hyde Park to those who are less interested in tourist attractions and more interested in Chicago’s history and culture.
The University of Chicago is located here. Its beautiful campus features Gothic-style architecture and is worth strolling around, especially in the fall. This also makes Hyde Park a good place to stay for prospective college students of the university.
Other attractions in Hyde Park include the Museum of Science and Industry, Frederick C. Robie House, and the DuSable Black History Museum and Education Center.
I recommend staying at Sophy Hyde Park, a highly-rated boutique hotel. It’s within walking distance of shops and restaurants and about a mile from the Museum of Science and Industry and the University of Chicago. If you’re a prospective student of UChicago, The Study at the University of Chicago is the perfect scouting hotel.
Pros of Staying in Hyde Park Neighborhood:
- Local charm and history
- Attractions to explore
- Vibrant local culture
- Walkable areas
- Lots of shops and restaurants
- Accessible by the Green Line
Cons of Staying in Hyde Park Neighborhood:
- Far from downtown attractions
- Limited hotel options
📚 Hyde Park Mini Guide 📚
Best Area to Stay for History & Culture
Google Map
✨ Best Hotels – Sophy Hyde Park • Hyatt Place Chicago-South/University Medical Center • The Study at the University of Chicago
🏠 Apartments – Browse Top Rentals in Hyde Park
🍽️ Where to Eat – Virtue Restaurant ($$$), Valois Restaurant ($), Ascione Bistro ($$)
🍸 Where to Drink – The Promontory, Woodlawn Tap, Cove Lounge
🎟️ Top Attractions – University of Chicago, Museum of Science and Industry, Frederick C. Robie House, Smart Museum of Art, Promontory Point, Jackson Park
Lakeview
👉 Best Area For Sports & Local Charm | ✨ Best Lake View Hotels: Hotel Zachary • Best Western Plus Hawthorne Terrace Hotel • City Suites Hotel
Lakeview is a more local neighborhood on Chicago’s North Side. It’s great for visitors catching a Chicago Cubs game at Wrigley Field. It’s also good for returning visitors who want to experience a local side of the city with a relaxed but still lively atmosphere.
A handful of smaller neighborhoods make up Lakeview. These include Wrigleyville, Boystown, Northalsted, Lake View East, and Central Lake View. Wrigleyville is the best area for Chicago Cubs fans since Wrigley Field is located here. Boystown is a great area for LGBTQ+ visitors, as it’s especially LGBTQ-friendly.
Lakeview is highly walkable, and there are cool places to explore. Check out Music Box Theatre and Southport Corridor. Or, simply walk down any of the main streets, like Broadway or Clark Street, and you’ll find endless restaurants and shops to browse. Lake Michigan borders Lakeview, so you’ll have easy access to less crowded Lake Michigan beaches, too.
Need a hotel? Hotel Zachary is a highly-rated boutique hotel across from Wrigley Field and right by the train. Best Western Plus Hawthorne Terrace Hotel is another good option and features a mix of traditional hotel rooms, suites, and rooms with kitchenettes.
Pros of Staying in Lakeview Neighborhood:
- Lots of shops, restaurants, and dive bars
- Famous live music venues
- Walkable
- Safe
- One of the easier places to drive in Chicago
- Accessible by the Brown, Purple, and Red Lines
Cons of Staying in Lakeview Neighborhood:
- Farther from the city center
📚 Lakeview Mini Guide 📚
Best Area to Stay for Sports & Local Charm
Google Map
✨ Best Hotels – Hotel Zachary • Best Western Plus Hawthorne Terrace Hotel • City Suites Hotel
🏠 Apartments – Browse Top Rentals in Lakeview
🍽️ Where to Eat – The Chicago Diner ($$), Southport Grocery and Cafe ($$), La Biznaga ($)
🍸 Where to Drink – Delilah’s, Wilde Bar & Restaurant, L & L Tavern
🎟️ Top Attractions – Wrigley Field, Music Box Theatre, The Vic Theatre, Laugh Factory, Belmont Harbor, Southport Corridor
Andersonville
👉 Best Area For Small Town Vibes | ✨ Best Andersonville Hotels: The Guesthouse Hotel • House 5863 – Chicago Bed and Breakfast
I love visiting Andersonville when I’m craving small-town vibes. This neighborhood is located on Chicago’s far north side, about 30 minutes by car or 50 minutes by train from the Loop.
It’s definitely a little out of the way. However, Andersonville is perfect for repeat Chicago visitors and people doing longer stays. It’s also ideal for those who want a more quaint and local experience while still having decent access to bigger attractions.
The main drag is filled with unique local shops and restaurants. It’s the perfect place to be if you just want to browse and window shop. Think home stores, bookstores, antique shops, bakeries, and more. Some of my favorite spots are Five Elements Home, The Understudy Coffee and Books, and FOLK.
Andersonville doesn’t have a ton of hotel options, but The Guesthouse Hotel is a beautifully decorated suite-style hotel nearby. I also recommend looking into vacation rentals.
Pros of Staying in Andersonville Neighborhood:
- Charming local atmosphere
- Tons of independently owned shops, restaurants, and businesses
- Not far from Chicago beaches
- Very walkable
Cons of Staying in Andersonville Neighborhood:
- Pretty far from downtown Chicago
- Farther from top attractions and museums around Chicago
- Limited hotel options
📚 Andersonville Mini Guide 📚
Best Area to Stay for Small-Town Vibes
Google Map
✨ Best Hotels – The Guesthouse Hotel • House 5863 – Chicago Bed and Breakfast
🏠 Apartments – Browse Top Rentals in Andersonville
🍽️ Where to Eat – Little Bad Wolf ($$), Lady Gregory’s Irish Bar & Restaurant ($$), Calo Ristorante ($$)
🍸 Where to Drink – Lady Gregory’s Irish Bar & Restaurant, Marty’s, Nobody’s Darling, Hopleaf
🎟️ Top Attractions – Swedish American Museum, Chicago Magic Lounge, Gethsemane Garden Center, Women & Children First
Tips for Staying in Chicago
Choose the Right Time to Visit
The best time to visit Chicago is between late spring through the fall. These times of year offer the most enjoyable weather for exploring the city. Although, the summer can get hot. Choose the right time to maximize your itinerary. This also makes it easier to know what to pack.
Pick a Neighborhood Based on Your Planned Activities & Attractions
One of my top Chicago travel tips is to select your must-see attractions, figure out where these activities are located, and decide where to stay accordingly. The Chicago Loop and other downtown neighborhoods put most visitors in a good spot. Although some visitors may have a better stay in other areas, depending.
Take Public Transportation Most of the Time
Public transportation is pretty reliable and extensive throughout the city. I encourage you to use public transportation to get around Chicago during the day. However, use ride shares if you plan on being out late at night just to be safe.
Do note that taking the train is a great way to go to and from the city and the airports. Hop on the Blue Line to reach Chicago O’Hare and the Orange Line to get to Chicago Midway. This is also a great tip for visiting Chicago on a budget.
Book Restaurant Reservations Ahead of Time
Book restaurant reservations as early as possible for peace of mind. This is especially important if you want to dine at popular Chicago restaurants like Girl and The Goat, Smyth + The Loyalist, Galit, and others.
Explore Beyond the Loop
Chicago has tons of exciting things to see, do, and experience downtown. But I believe the best of Chicago lies beyond the Loop in different neighborhoods. I highly encourage you to venture beyond downtown and explore Chicago neighborhoods beyond the ones in this guide.
📚 Related Reading: 60 Things to Do in Chicago
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 where to stay in Chicago at minute mark 09:53. Here are the hotels I mention in the episode:
The host, Betty, and I also discussed the best things to do in Chicago (04:21), 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.
FAQs
What are the best areas to stay in Chicago for first-timers?
The Chicago Loop, River North, and Magnificent Mile are the best areas to stay in Chicago for first-timers because all these areas are in downtown Chicago. These neighborhoods are centrally located and within walking distance of shops, restaurants, and top attractions.
What are safe areas to stay in Chicago?
Lincoln Park and Gold Coast are safe areas to stay in Chicago. However, staying in downtown areas like the Chicago Loop, River North, and Magnificent Mile are generally safe for visitors because these areas are touristy.
When is the best time to visit Chicago?
The best time to visit Chicago is in the summer and fall. These seasons bring good weather and lots of festivals and events to the city.
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I hope you found this guide helpful and feel better prepared for your visit to the Windy City. Read our 5-day Chicago itinerary for more planning tips.
Hi,
Many of the Airbnbs I’m finding are in the Near North area, which I see is between the neighborhoods highlighted here. Is there an important reason why that area isn’t featured? Thanks for clarifying!
Hi Lea!
Nice blog! Congrats!
We are travelling with our kids to chicago next October. We have found two hotels that match our budgrt and our big families requirements. One is in the southest part of the loop near the aquarium, and the other is in river north. Both locations seem nice but which one would you recommend us?
Thank you!
Joan
Hi Joan! I recommend the River North hotel over the South Loop one, just because River North is a little more central when it comes to Chicago’s main attractions. For example, you’ll be closer to the Mag Mile, Navy Pier, and Millennium Park, as well as shops and restaurants. Enjoy your trip with your family!
Hi, our family are meeting up from different parts of the world, in Chicago and want an apartment somewhere near “Soldier Field “
Would you be able to point us in the right direction?
We would be looking for a 3 bedroom apartment. Thank you so much!
Hi Mags! I’d recommend staying in South Loop. This will put you close to Soldier Field so you should be able to walk there instead of drive or Uber. You’ll also be reasonably close to other top attractions like the Field Museum, Shedd Aquarium, Art Institute, and the Bean. You can browse apartment rentals here. I hope this helps!
Hey! Thank you for the informative articles! My husband and I are visiting Chicago for the first time, the first week of August, to celebrate his birthday! He is a steak snob, LOL, and I would like to take him to a nice dinner. I want to stay in the Loop area to be close to all the attractions. What are your restaurant recommendations? Thanks!
Hi Misa, how fun! Check out Maple & Ash, Gibsons Bar & Steakhouse, or Le Bouchon! All these places are known to have great steaks. But be sure to make reservations ahead of time (like now) just to ensure you get a table. Maple & Ash and Le Bouchon can be harder to get into. The first weekend in August is also when Lollapalooza happens, so the city might be extra busy depending on what day you arrive. I hope this helps and have a wonderful trip!
Which hotel would you recommend in Evanston? Also, is it a safe area?
Hi John, Evanston is a safe area. Just note that it’s about 45 minutes to an hour outside of downtown Chicago. As for hotels, the Graduate by Hilton Evanston is filled with charm and character. Meanwhile, the Hilton Garden Inn Evanston is a good choice but a little more budget-friendly.
My husband and I are first time visitors looking for a hotel on the water with a balcony, as boat watching and walking along the waterfront would be a nice evening pass time. Any recommendations are greatly appreciated!
Hi Dawn, a hotel on the lakefront with a balcony will be a little more difficult to find. However, I have a few recommendations you might be interested in! First is the Drake Hotel. It’s in the Streeterville neighborhood and sits right above Oak Street Beach. Second is the Chicago Athletic Association in the heart of the Loop. It’s a beautiful boutique hotel right across from Millennium Park, with Lake Michigan in the background. Third is LondonHouse Chicago, which doesn’t necessarily have lake views, but it sits right above the Chicago River. Lastly is the Radisson Blu Aqua Hotel, which includes rooms with balconies. It’s not right on the water, but it’s pretty close, and you should have views of the lake. Regardless of where you choose to stay, I’d put in a special request for lake-facing views. I also want to add that all of these hotels are within walking distance of the Lakefront Trail, and are centrally located to main attractions. I hope this helps!
Great information and so many choices. We will be arriving via Midway. Staying 5 nights. First day going to a cubs game. First time in Chicago and riding bikes along the river walk sounds fun. Can you rent/ride E-bikes. We are in our 70s and graduated to E bikes. We love nature. Maybe a boat tour? Won’t have a car. Where would you recommend us staying?
Hi Susanne! I think Streeterville would be a great choice for you. It’s close to the Red Line, which is the same line you’ll need to take to Wrigley Field. It’s situated next to the lake, so you can easily hop on the Lakefront Trail to ride bikes (you’ll want to ride bikes on the Lakefront Trail, not the Riverwalk, which is mostly meant for walking). You can rent bikes and e-bikes through Divvy. You’ll find docking stations all over the city, but I recommend downloading the Divvy app ahead of time to help you locate the stations and get bikes quickly. Streeterville is also pretty central, so you can easily head to Navy Pier or the end of Michigan Ave for boat tours! Plus, parks like Millennium Park and Lincoln Park aren’t too far away. I hope this helps!
Hi Lea! Very useful information. We’re driving to Chicago (our first time) from NC in mid April. Family of four (2 boys 17 and 11), hoping to see as much as possible in 4 or 5 days including Cubs game on our last night. We’d like to stay near the downtown, but I read parking could be expensive. What neighborhood would you recommend? (With good access to public transportation, don’t want to drive while in the city)Thanks!
Hi Alex,
I’m actually from North Carolina originally, so welcome! Parking is definitely most expensive in the downtown Loop, but there will likely be fees in most places. As for areas, I think Lincoln Park or Old Town would be a great fit for you and your family. Both neighborhoods are located on Chicago’s near north side, so you can easily hop on a bus or train to reach the Loop and popular attractions. You could even hit the Lakefront Trail and rent Divvy bikes to reach places like Navy Pier, the Field Museum, and Shedd Aquarium. You’re likely going to have to pay a parking fee at any hotel, but it may be slightly cheaper in these areas. A vacation rental may also be a great choice, and some might have parking since these areas are a little more residential. Just check ahead of time, and be sure not to leave anything in your car when it’s parked, just as a safety precaution. Additionally, Wrigley Field is on the north side, so you should have more convenient access if you stay in either Lincoln Park or Old Town. Some other guides you might find helpful are my 5-day Chicago Itinerary, Getting Around Chicago, and Things to Do in Chicago. Have a wonderful visit!
Thanks so much for this info. We are traveling to Chicago in June for a concert at Soldier field, mostly for our son, it is a rap concert. We are foodies, but also love the jazz scene. What is your best recommendation for airport Midway or O’Hare? Also 3-4 star hotel. It’s our first time and we want to see everything.
Hi Alisa, How exciting! I recommend staying in the South Loop for your trip. It’s the best area to stay for an event at Soldier Field. Plus, this area is conveniently located close to big attractions. You’ll easily be able to visit the Field Museum and Shedd Aquarium. Millennium Park, Navy Pier, and the Lakefront Trail are close by as well. If you like jazz, Buddy Guy’s Legends jazz club is close by! Homewood Suites and Hilton Chicago are good hotel options in this area. For airports, both are good options, just different. Midway is much smaller than O’Hare and less chaotic in general. I personally fly in and out of Midway all the time and find it easy to navigate and there are usually shorter lines at TSA. You can take the Orange Line directly to and from Midway into the Loop. O’Hare has much better amenities, but it’s huge and larger to navigate. Similarly, you can take the Blue Line directly to and from O’Hare into the Loop. You can’t really go wrong with either airport, but like I said, they’re just different. Additionally, all the major airlines fly into O’Hare while Midway tends to fly smaller, regional airlines. For more trip planning ideas, you might like my Chicago itinerary and list of things to do in Chicago and Chicago restaurants. I hope this helps!
Hello.
My husband and I have been looking for at a two bed rental for 8 nights in July. I have found a nice looking place that I would like to book. It’s in Oak Park. Is that a nice area? We are a fairly quiet couple so we don’t not want anywhere too busy. Many thanks.
Hi Jacqueline, Oak Park is a great area! It’s most notable for featuring many examples of architect Frank Lloyd Wright’s work, including his home and studio. Oak Park even made our list of best places to travel in 2025 🙂 This being said, Oak Park is a suburb of Chicago. It’s about a half-hour drive from the Loop (downtown area) or a 45-minute train ride. It’s a good area to stay if you’re looking for peace and quiet and want to head into the city a time or two. However, it’s not the best place to stay if you want to visit Chicago attractions each day of your trip. If you’re looking for an area that offers similar peace and quiet but is closer to attractions, I recommend Lincoln Park. I hope this helps!
Hi Lea!
Thank you for that article that is very useful.
We are planning to visit Chicago from spain next October 2025 as I am running the Marathon. We are a family of 5 (2 kids and a baby). What would you recommend us? We are thinking about lincoln park or lakeview but maybe it tooks so long to get to the main must see tourist attractions. Does airbnb work well in chicago?
Yours sincerely
Hi Joan, How exciting! I would definitely recommend Lincoln Park – it’s a little closer to the downtown Loop than Lakeview. Plus, it’s super family-friendly (for example, the actual park, Lincoln Park, and the zoo are here). You can easily hop on a bus from Lincoln Park and head straight into the Loop for tourist attractions. The neighborhood is largely residential so you should be able to find a solid selection of Airbnbs and VRBO rentals. Good luck at next year’s marathon!
Hi Lea,
Thank you for such a detailed review of Chicago including places to stay and things to do. I’m planning on visiting Chicago in March 2025, just wondering is this a good time to visit and if the Riu Plaza Chicago is a good pick. It will be 4-5 old friends (45+) just wanting to kickback and have good time any suggestion of where to go.
Hi Dana, March is a bit hit-or-miss when it comes to weather. Spring in Chicago can be a bit unpredictable with cold days and rain, but every now and then, a warm, sunny day pops up. I’d pack a coat, layers, and an umbrella. Expect cooler weather generally. This being said, March is much less crowded than other times of year in Chicago (aside from St. Patty’s day – which is HUGE here) which is great for visiting attractions and popular restaurants with less hassle.
The Riu Plaza Chicago looks like a great pick! It’s located right off the Magnificent Mile so you’ll have plenty of shopping nearby. Plus, this area is super walkable to places like Millennium Park, Navy Pier, the Riverwalk, the Lakefront Trail, etc. This location will definitely give you that bustling city vibe. As for activities, I have a whole guide to things to do in Chicago 🙂 My last recommendation would be to check out some neighborhoods if you have the time! From what you’ve shared, I’d recommend Lincoln Park and West Loop. Have a fantastic trip!
Planning a trip to Chicago in January (coming from Canada) to watch a Blackhawks game. Where would be the best place to stay and is it walkable in January?
Hi Ron! I always recommend West Loop to those attending a game at the United Center. West Loop is walkable with tons of shops and restaurants (it’s actually known as Chicago’s “foodie neighborhood”), and it’s the best neighborhood for being close to the arena. From here, you could walk if you wanted to, but you could also take a bus or the train via the Green Line (take Morgan to Damen). It’ll likely be pretty cold in January. Regardless of if you walk or take the bus/train, I suggest packing a warm down coat, gloves, a hat, and boots. The sidewalks and roads are always salted pretty well, but it’s still important to have good winter shoes in Chicago. Hope this helps!
My daughter and I are going to a campus tour at Loyola University and then attending a concert at The Salt Shed. We may also be traveling to Chicago via Amtrak instead of driving. Where would you recommend staying for 2 nights and tips on how to travel from each place?
Hi Crystal,
How exciting! If you visit via Amtrak, you’ll arrive at Union Station. This station, the university, and Salt Shed are all in different spots across Chicago, so there’s not really one area that I’d recommend as the “best” in this case. However, it would be helpful for you to stay near the Red Line if you don’t drive into Chicago. The Red Line will take you up to Loyola University, and it has a station near the Salt Shed (about a 15-minute walk). I’d also recommend staying on the North Side since it’s closer to these places. Old Town could be good if you want a more chill, local vibe. Otherwise, the northern part of the Loop and near the Magnificent Mile might be good. Plus, these 2 neighborhoods are close to tourist attractions.
As for transportation, a mix of trains, buses, and ride-shares will make the most sense. I’d recommend taking the train to and from Loyola, taking a bus or train to the Salt Shed, and then Ubering home from the Salt Shed after your show. I also have a guide to getting around Chicago. Have a great trip with your daughter!
We decided to stay at The Loop thinking it would be walkable and full of options for food, entertainment and shopping. What a disappointment. Our hotel is good but non refundable. This area is dirty, not much original food, very touristy. There’s literally nothing really fun. At night they work in the sewer lines and the smell is disgusting. A super hard pass.
Thanks for the very informative post which I stumbled across fortuitously. I’m from South Africa and will be spending time in Chicago in early October ’24 for a week. I have absolutely no clue on what/where/how 😊 and wondered if you’d be open to chat to me directly via email/WA. TIA
Hi Leila, I’m glad you stumbled across my post and found it helpful 🙂 This Where to Stay in Chicago guide breaks everything down that visitors would want to know – the best neighborhoods for different types of travelers, hotel recommendations, mini-guides for each neighborhood, and more. Generally speaking, Downtown Chicago areas like the Chicago Loop, River North, and Streeterville are good for first-time visitors like yourself. However, each Chicago neighborhood offers something different. If you have any specific questions I’d be happy to answer here in the comments section! Thank you!
Hi! Visiting Chicago in two weeks, family of 6. Going to both MLB stadiums, opposite weekends. Of course we want to do all the touristy things but not opposed to moving locations in order to do all things Chicago. Would love places with walkable distances with the kids. Recommendations please
Hi Megan! The two MLB stadiums (Wrigley Field & Guaranteed Rate Field) are a bit far from each other and on opposite ends of the city. I recommend staying in the Streeterville neighborhood downtown if you want to stay in one central place for your whole trip. Streeterville is within walking distance of tons of major attractions and close to the Red Line, which goes to both stadiums. However, if you’d rather split up your trip into two locations, I recommend Lakeview for being within walking distance of Wrigley Field. And then South Loop for being closer to Guaranteed Rate Field but still close to family-friendly attractions and downtown Chicago. I hope this helps and have a wonderful trip!
Hi!! I’m wondering where to stay for a weekend away with my hubby!! First timers who enjoy good food music and something non touristy. We like local shops rather than trendy shops and small town local vibes. We would only be in town for a few nights. We would also like easy access to trains if we want to explore other parts of city.
Hi Victoria, my first recommendation would be Andersonville! It’s a neighborhood on Chicago’s far north side but it feels like a vibrant small town. It’s super cute and will definitely give you a taste of Chicago’s local side. I visit here myself when I’m craving that small-town vibe. Andersonville is also full of really neat independently owned shops and restaurants. The only downside is that it’s a bit farther from downtown Chicago – about 30 minutes by car or 50 minutes by train via the Red Line. If Andersonville is too far, I recommend Wicker Park since it has awesome spots for food and live music. Wicker Park is really walkable and has easy train access to reach the downtown Loop via the Blue Line. Just note that Wicker Park has a more bustling atmosphere and less small-town vibes. Be sure to read my Chicago neighborhoods guide to get a better feel for each of these places!
Hi Leah, I’m visiting Chicago for the first time in May/June and want to stay a few weeks. My priority is seeing architecture highlights of Chicago and getting a good experience of Chicago as a city. Any suggestions of which neighborhood to stay? I’m open to Air BNB or hotel with kitchenette. I’ll have my dog with me. Thanks for any help you can offer!
Hi Wendy, for a longer stay with these things in mind, I’d recommend the Old Town/Old Town Triangle area. This area is walkable and has a more local feel to it with plenty of shops, restaurants, and bars. Plus, the residential streets are full of beautiful old homes. Being here will still give you easy access to downtown attractions and historical landmarks via walking or taking the bus. You can also easily hop on a bus to head down to Hyde Park, which is a rich architectural area since it’s home to the University of Chicago and the Robie House. The Old Town area is also a short walking distance from Lincoln Park and the Lakefront Trail, which is great for walking your dog. Similarly, the Gold Coast neighborhood is a good choice and is right next to Old Town. If you don’t have any luck finding rentals in this area for your criteria, Lincoln Park and Wicker Park are good options to check out, too. Hope this helps!
Hi Leah,
I’m going to be in Chicago in a few weeks with my 22, 20 and 17 year old daughters. Which area would you recommend staying in? We will do some shopping. Hoping for some mainstream shopping but also interested in smaller stores and vintage. Nothing high end like Prada. We are also are considering a comedy show and maybe some spa services.
I’m wondering which neighborhood is best for this age group. Also if you would recommend AirB&B in addition to hotels.
Thanks!
Hi Nikki, I’d recommend Wicker Park. You’ll find mainstream shops like Urban Outfitters, Free People, Adidas, etc., and tons of vintage and thrift shops. You’ll have easy access to the Blue Line so you can take the train into the Loop (downtown) for more shopping. There are spas in the area as well as tons of restaurants. Wicker Park has a more youthful vibe to it than other Chicago neighborhoods so it would be a great fit! Lastly, you can easily take a bus or Uber to Second City Comedy Club and there’s even a comedy theater in Wicker Park, called the Den Theatre. The Robey Hotel (mentioned in this article) would be a great choice as it’s in the heart of Wicker Park. As far as Airbnbs or rentals go, I’d just make sure you’re within easy walking distance of the Damen train stop and you should be good to go. Be sure to read my Wicker Park guide for more things to do. Have a wonderful trip!
Hi, I’m planning my trip and I’m currently between the River Hotel (mostly because of your recommendation) and the CitizenM Hotel and I wanted to know which one you would recommend more and why?
I’m curious why you recommend River Hotel as best overall, it seems more business people directed
Hi SB, I think both hotels offer good value and have fantastic, central locations. One of the main differences is that the River Hotel overlooks the Chicago River and Riverwalk. It offers similar views as riverfront hotels while still having good value but a cheaper price point. This being said, the CitizenM Hotel is still a highly-rated hotel and a good choice! It has an awesome central location and offers a more modern, trendy atmosphere. Have a wonderful trip to Chicago!
Hello,
Which downtown hotel would be the best place to stay in January. Good food and bar, one night, basically too cold to walk to venture out.
Hi Jill, the Chicago Athletic Association Hotel (mentioned in this article) would be a great option. It’s a boutique hotel right in the heart of downtown. It has tons of amenities on-site including restaurants, a bar, and a game room. The location also puts you within super easy walking distance of Millennium Park and the Art Institute if you do go out. I hope this helps and have a wonderful trip to Chicago! Stay warm!
Hello Lea. I am contemplating various areas to stay
I will be there 4 nights in June with my 16 yr old
Cub game one night
White Sox game another night
Would like easy access to the beach, Gibson steak house, navy pier ( walking, train access is fine to all)
Please let me know your thoughts
Thank you
Hi Darren, the Streeterville area would be an ideal place to stay for all of these things. You’d be within easy walking distance of Gibson’s, Oak Street Beach, and North Avenue Beach, as well as Navy Pier. This would also give you easy access to the Red Line which takes you to both baseball fields. The Gold Coast area is another good option. Have a wonderful trip!
Thank you for this very detailed breakdown of Chi town.