Where to Stay in Chicago, Illinois: 5 Best Areas & Hotels

Planning a trip to Chicago and trying to figure out where to stay? We’ve got you covered!

Chicago is packed with neighborhoods (around 100), so figuring out which one suits you best can take a little time. We ended up loving every area we visited, as each one offers something different. Some are super walkable and ideal for sightseeing; others are better for nightlife; a few feel quieter and more scenic, or are perfect for a romantic trip. You really can’t go too wrong here, as it all comes down to the kind of trip you’re after. 

That’s why we’ve broken down the best places to stay, along with the hotels to book for every budget and style, so you can plan the trip that’s right for you. Let’s get into it! 

Overview of the Best Areas to Stay in Chicago 

Chicago doesn’t have one “best” area to stay in; it all depends on what you’re after. You might be drawn to the upscale shopping of the Magnificent Mile, the hip vibe of Wicker Park, the polished feel of Lincoln Park, or the city buzz of The Loop, with more than 100 neighborhoods, the city changes block by block. 

If it’s your first time here, staying central usually makes life easier. The Loop, Magnificent Mile, River North, and Fulton Market are some of the best areas for sightseeing, eating out, nightlife, and getting around without wasting time. You’ll be close to the Riverwalk, the lakefront, museums, and plenty of places to unwind after a long day, with hotels for every budget, too.

Still, there’s more to Chicago than downtown skyscrapers and tourist stops. If you’ve got the time, look further out. Some of our favorite parts of the city are the ones many visitors skip. Areas like Wicker Park and Lincoln Park offer a more local feel without losing convenience.

Getting around Chicago is easy, too! The “L” train is usually the smartest option, with Uber and Lyft useful when you’ve overdone the walking. 

Here are our top five areas to stay in Chicago, plus hotels for every budget and style:

• The Loop – Best for first-time visitors – This is Chicago’s business hub and one of the best areas to base yourself for sightseeing, theatres, art galleries, and fine dining. River Hotel is our top pick here, thanks to its great views, modern rooms, and 4-star perks, all at a lower price than most riverside hotels.

• Magnificent Mile – Best for luxury travelers – If you want to be right in the middle of it all, just steps from the Riverwalk and surrounded by high-end shops, this iconic stretch won’t disappoint. Riu Plaza Chicago is one of the newer additions here, with clean, modern rooms and a generous breakfast included.

• River North – Best for a lively vibe, nightlife, & convenience – Art galleries and trendy nightclubs keep this area buzzing, drawing in architecture lovers and foodies, plus anyone who enjoys partying after dark. The Royal Sonesta Chicago River North is a stylish, eco-friendly pick with perks like an indoor pool and rooftop terrace, making it a great base for getting to know the area without blowing your entire travel budget. 

• West Loop/Fulton Market – Best for foodies & modern amenities – With famous “Restaurant Row” nearby and old warehouses turned into luxury lofts and offices, these neighborhoods promise a fun stay without feeling like a tourist zone. Our favorite option here is Hampton Inn Chicago West Loop, thanks to its gorgeous sun terrace with cozy sofas, free breakfast, and a 24-hour snack shop for those late-night cravings.

• Wicker Park & Lincoln Park – Best for a local, creative atmosphere – Street art, indie venues, and laid-back hangout spots define Wicker Park, while Lincoln Park has a more upscale, residential feel with its huge park and zoo. Hyatt Place Chicago Wicker Park is an excellent stay for families, with spacious suites and one of the largest sun terraces in the area. 

Where to Stay in Chicago 

The Loop

BEST FOR FIRST-TIME VISITORS

Pros 

• Great locations with easy access to public transport
• Great mix of upscale dining and theatre options
• Packed with landmarks, many within walking distance

Cons 

• Higher prices for dining, parking, and accommodation
• Can feel a bit quiet after work hours

The Loop is Chicago’s downtown core and easily the most practical place to stay if you’re here to see it all, especially if it’s your first time. You’ve got Millennium Park, the Art Institute, Willis Tower, and Grant Park basically on your doorstep, so you can cover a lot in a little time, ideal for a packed itinerary.

It’s incredibly convenient and well-connected, and it can feel like the busiest place on Earth at 1 pm on a Wednesday, but once the workday ends, things quiet down fast (almost ghost-town level), giving it more of a business-district feel at night.

It’s the opposite of areas like River North or West Loop, which stay lively after dark. That said, The Loop is ideal for first-time visitors, Broadway fans, and anyone wanting those Chicago skyline views (the world’s most famous skyscrapers are right here). Food-wise, there’s everything from casual bistros to Michelin-starred restaurants, and with every “L” line running through here, getting around is as easy as it gets.

It feels safe and lively during the day, but once offices close, we’d recommend sticking to well-lit pockets like the Riverwalk or Theatre District.

JW Marriott Chicago – $$$

JW Marriott Chicago is the perfect luxury getaway in the Windy City, just a stone’s throw from Millennium Park. What we love most is not only its location in the heart of the Loop, but the fact that it’s set in a historic landmark building, something you feel with every step. 

And then there are the perks. For starters, there’s an executive lounge with a gourmet breakfast each morning. By afternoon, the spa quickly becomes part of your routine, with great treatments and an indoor pool you’ll likely come back to more than once. 

For dinner, The Florentine serves Italian classics (nothing like a wood-fired pizza on a rainy Chicago evening). The hotel also has a grand ballroom with domed ceilings, so don’t be surprised if you walk past a wedding or gala. Prices average from $240 USD to $900 USD per night, depending on the room and season.

If JW Marriott Chicago is all booked up, Pendry Chicago is a great backup just a few blocks away, yet still close to Ohio Beach and the Art Institute. There’s a games room and live music at the bar, but the rooftop deck is where you’ll likely spend most of your time, with comfy sofas and great views. 

Renaissance Chicago Downtown Hotel is another fantastic option in the area, located in the Theater District just across from the Chicago River. It’s modern, a bit more upbeat, and has a popular rooftop with some of the best vistas over the Riverwalk, plus an artist studio showcasing local art. 

River Hotel – $$ 

Just a short walk from The Magnificent Mile, River Hotel is our favorite choice, and it ended up being a great find, right on the river but without the hefty price tag of nearby hotels. It’s set inside the historic Mather Tower (very Gothic on the outside), but inside it’s modern and simple. 

Our room had a cozy feel from the moment we walked in, and just enough space to relax after a long day. You can even have a yoga kit or exercise bike sent to your room (we admired the idea more than we used it).

There’s also a complimentary wine and cheese hour from 5 pm, Monday to Thursday, which we didn’t miss. Plus, dogs stay free, which is always a nice bonus. Prices range from $100 to $500 USD per night, making it a solid, well-located option.

Another mid-range priced option in The Loop is Hyatt Regency Chicago, just a 5-minute walk from Millennium Park. As the largest hotel in the city, it comes with a wide range of services, several dining spots, spacious suites, and even indoor access to the Illinois Center (especially handy in winter).

A bit closer to the Art Institute of Chicago, Hampton Inn Majestic Chicago Theatre District is a reliable choice within easy walking distance of the Willis Tower Skydeck. Set inside the iconic CIBC Theatre building, it even has a private entrance to the venue (hard to beat if you’re catching a Broadway show), plus comfortable rooms and free breakfast to start the day right.

Club Quarters Hotel Central Loop  – $  

Don’t think you have to sacrifice style for price at the Club Quarters Hotel Central Loop. Even with lower rates, it covers all the essentials! There’s an English-style pub, a gym, and modern rooms, as well as a business lounge if you need to get some work done.

What makes it stand out is the “private club” feel rather than a typical hotel setup. The Club Living Room is the heart of it all, where you can sit back in a comfy armchair by the fireplace in a cozy, home-like atmosphere. You’ll also find workstations and free La Colombe coffee (which you should definitely take advantage of).

Location-wise, it’s an easy walk from Union Station and close to spots like the Chicago Fed Money Museum and Willis Tower, so getting around is super easy. Prices start from around $100 USD, making it one of the more affordable stays in the Loop.

Congress Plaza Hotel Chicago is a great budget-friendly backup right on iconic Michigan Avenue, directly across from Millennium Park, so the views are hard to beat. Step inside and you’ll notice the old-world charm straight away with high ceilings and grand chandeliers throughout.

If you’re after something a bit more exclusive and smaller, The Buckingham Hotel fits the bill, located on the 40th floor of the Chicago Stock Exchange building. It feels quiet and private with access to an Athletic Club and free breakfast, too, which is always a nice bonus.

Magnificent Mile

BEST FOR LUXURY TRAVELERS

Pros 

• Home to many 5-star hotels and upscale stays
• Packed with high-end brands and restaurants
• Easy to get around on foot

Cons

• Among the most expensive areas in the city
• Rarely quiet, always busy

Centered around Michigan Avenue, the Magnificent Mile is Chicago’s most polished and tourist-friendly area, lined with high-end shops, restaurants, and upscale hotels, but also fun, family-friendly spots like American Girl Place and the Museum of Ice Cream.

This stretch was once just a dirt road lined with mansions and even a massive brewery. Things changed, though, when the Michigan Avenue Bridge (now DuSable Bridge) opened in 1920, and the Loop finally connected to the north side, drawing in the crowds.

But the Magnificent Mile isn’t just about luxury brands and five-star hotels. You’ve got landmarks like the 360 Chicago Observation Deck, historic buildings like the Chicago Water Tower (one of the few to survive the Great Fire of 1871), plus easy access to the Riverwalk. In fact, what we love most about this area is how close you are to the lake, right where the city meets Oak Street Beach (which feels a bit like a resort city with the beach steps from your hotel). 

Overall, it’s a great pick if you enjoy a mix of sightseeing, a bit of luxury, time by the beach, and busy city streets. It’s safe and central, perfect if you want that classic, easy Chicago experience with everything close by.

The Peninsula Chicago – $$$ 

The Peninsula Chicago is a AAA Five Diamond hotel on the Magnificent Mile, so yes, this is where you go all in. But what makes it stand out isn’t just the grandeur; it’s more about the little extras you don’t really see anywhere else, like a chocolate buffet (not ideal if you’re avoiding sugar) or a half Olympic-size indoor pool. There’s also an ice skating rink open in winter!

It blends Asian-style service with warm Midwestern hospitality, making it feel less formal and helping you settle in comfortably without feeling overwhelmed. Best of all, if you book directly, you can check in as early as 6 am and check out as late as 10 pm (for free), which feels like a bonus in itself. Prices start around $480 USD and can go up to $1,000 depending on the room and season.

Just one block east of Michigan Avenue, Hyatt Centric Chicago Magnificent Mile is a fantastic, more affordable alternative if The Peninsula Chicago is fully booked. We love it for the little perks, like the on-site Starbucks (so you can grab your chai without leaving the building) and the smart rooms with motion-sensor nightlights.

Located on floors 30 to 46 of the 900 North Michigan building, Four Seasons Chicago keeps you central with a bit of height and absolutely stunning views. It feels luxurious but not too formal, with family-friendly perks like no extra fees for children under 18, plus things like an ice cream cart or even a Martini Man showing up at your room for in-room cocktails. 

Riu Plaza Chicago – $$ 

Riu Plaza Chicago makes staying on the Magnificent Mile possible without blowing your entire travel budget. It’s a fairly new addition to the area, and it already stands out for many things, including its modern European style. Rooms here feel fresh and uncluttered, with hardwood-style flooring instead of the usual carpets you’ll find in the historic hotels nearby. 

The real highlight, though, is the rooftop bar on the 27th floor with a glass-bottomed balcony, which has become a popular spot for photographing (might make you feel dizzy, but it’s worth the views). There’s also a 24-hour gym if you feel like balancing things out.

Breakfast is included, and it’s a proper American-style buffet, which isn’t something you’ll always get around here for free, even at higher-end hotels. With prices starting around $200 USD per night, we think it’s a pretty solid deal for this location.

Residence Inn by Marriott Chicago Downtown Magnificent Mile is another stylish option nearby in the Streeterville neighborhood (so not technically on the Mile, but close enough). Each room comes with a fully equipped kitchenette, which is especially handy if you’re traveling as a family or just want to save a bit by cooking in.

Right around the corner from Northwestern Memorial Hospital, Aloft Chicago Mag Mile is a convenient mid-range choice that offers great value. It has a fun, slightly artsy vibe (it sits on the former site of the Museum of Contemporary Art (MCA)), with live acoustic music and social hangout spaces that make it a great pick for solo travelers or couples.

Hilton Garden Inn Chicago Downtown/Magnificent Mile – $ 

Hilton Garden Inn Chicago Downtown/Magnificent Mile is one of those places that proves you don’t need to spend your savings to stay in the heart of Chicago. You’re just steps from Michigan Avenue, surrounded by great food spots, and with the Grand Red Line at your doorstep, getting around is super easy.

Inside, it’s simple but practical. The indoor pool is always a welcome extra (especially for families or after a day of being a tourist), and the lobby mini-mart has everything you need, from late-night snacks to toiletries you can pick up even at 2 am.

We love the rooms here, with desks and ergonomic chairs, ideal if you need to get some work done. With prices starting around $100 USD per night, it’s one of the best deals in the area.

Just a short walk from the 360 Chicago observation deck (Hancock Building) and Water Tower Place, Warwick Allerton Chicago is right in the middle of everything. It’s one of those classic Chicago stays, a 1920s-era hotel with Art Deco charm and a bit of history to it (apparently even Frank Sinatra and the Rat Pack used to hang out here, which says a lot).

If you’re after first-class amenities but don’t want to overpay, Hilton Chicago Magnificent Mile Suites fits the bill, with spacious suites and a top-floor indoor pool and gym if you want to keep up with your routine. Location-wise, it’s hard to beat, just one block east of the Magnificent Mile and a short walk from the Lakefront Trail, so you’re right in the middle of it all. 

River North 

BEST FOR A LIVELY VIBE, NIGHTLIFE, & CONVENIENCE

Pros 

• Super walkable and easy to get around
• Packed with clubs, restaurants, art galleries, and bars
• Great access to public transport

Cons

• Can get noisy at night, especially on weekends
• Fewer parks than in other parts of the city
• Higher prices for dining, hotels, and drinks

River North is one of the liveliest parts of Chicago, known for its buzzing restaurant scene, cocktail bars, and rooftop lounges, so if atmosphere matters, this is one of the best areas to stay.

Just across the river from downtown, it gives you easy access to the main sights while offering a more energetic, social feel. With art galleries, the Chicago Riverwalk, and some of the city’s best dining and clubbing, it’s a favorite for anyone who wants to enjoy a good night out in Chicago.

Beyond the nightlife, we also love how easy it is to get around on foot. It’s no wonder the area is often called a “Walker’s Paradise.” Locals can comfortably live here without a car, so short-term visitors will have no trouble at all. If you want to explore further, you’ve also got easy access to the CTA Red and Brown lines.

Because of its fast-paced, trendier vibe, we’d say it suits young professionals, couples, and art lovers best. That said, families shouldn’t rule it out, as there are some excellent family-friendly stays here, including a few budget options too (yes, even in this upscale area).

The Langham Chicago – $$$ 

The Langham Chicago is set inside a landmark building and ranks among the best hotels, not just in Chicago but across the U.S. With personalized butler service and an incredible health club (large indoor pool too), it’s probably the closest you’ll get to a resort-style stay right in the middle of the city.

It’s modern, with spacious rooms and floor-to-ceiling windows that give you some seriously good views over the Chicago River and skyline. We think it’s a great pick for a stylish city break or even a family trip with a bit of luxury on the side (there’s a Kids’ Suite with toys and games, plus a Cinema Suite for private screenings). 

And if you’re into art, you’ll find around 150 pieces throughout the hotel! Prices usually start around $400 and can go up to $1,700 USD per night, depending on the season.

Just a short walk away, The Westin Chicago River North is only a 10-minute walk from the Magnificent Mile shops. This spot is all about convenience and wellness, with spa-like bathrooms and even lavender oil on your nightstand to help you sleep.

Nearby, Kinzie Hotel is another stylish option, just a short walk from the House of Blues and plenty of trendy bars. The hotel has Chicago-inspired decor, with historic city maps in each room, plus breakfast served on each floor (always a win when you don’t have to deal with the lobby buffet crowds).

The Royal Sonesta Chicago River North – $$ 

The Royal Sonesta Chicago River North is a fantastic mid-range option if you want comfort with a bit more character. It’s artsy, spacious, well-located, and comes with excellent dining, while the colorful interiors make it feel like a stylish condo rather than a hotel.

Rooms here are spacious and comfortable, which makes it an ideal spot for couples, families, or anyone wanting style without splurging. You’ll also have access to an indoor pool and a sundeck (comes in handy when you need a break from the city streets).

The location is hard to beat, too, just a 1-minute walk from the CTA Red Line, steps from the Navy Pier, and Millennium Park. Prices for a standard king with city views usually range from $160 to $675 USD per night. 

Right around the corner, Homewood Suites by Hilton Chicago-Downtown is a smart, high-end option (minus the high price tag) in the same building as Eataly, with plenty of upscale restaurants right outside. The spacious suites come with full kitchens and grocery shopping services, making it especially handy for families or anyone staying a little longer. 

Moxy Chicago Downtown is also within easy walking distance of the Water Tower Chicago, but this one is more of a party hotel than a family stay. There’s a lively social vibe, a mocktail waiting with your room key, and a lounge packed with oversized games like foosball and shuffleboard. 

Freehand Chicago – $

Freehand Chicago combines hostel energy with hotel comfort, offering private rooms, bunk-bed options, and common spaces that feel more like a cozy living room than a standard hotel. You’ll notice tribal-inspired decor throughout, from the throw pillows in the rooms to the totem poles around the bar, giving the whole place a cool, artsy vibe. It appeals more to younger travelers, but that doesn’t mean families should rule it out.

Overall, we think it’s a solid choice for budget-conscious travelers who don’t want to sacrifice style for price. There’s always something happening here, from yoga sessions and live DJs to an award-winning bar, and you’ve also got a high-end cafe (the Nicaraguan coffee here is a must).

It’s close to the Grand Red Line station, which means you get easy access to both O’Hare and Midway airports. Rates usually start around $80 USD per night, a great bargain for this area.

A great, affordable backup in the area, Hotel Felix is just a short walk from landmarks like Holy Name Cathedral. This eco-friendly hotel comes with a few fun extras too, including cork flooring in the meeting rooms, a sushi spot, and a French bistro with live music from Wednesday through Saturday. 

Godfrey Hotel Chicago is a more modern choice with a lively social scene and a gorgeous indoor and outdoor rooftop lounge, complete with a state-of-the-art retractable roof. It’s located just steps from State Street shopping and surrounded by popular restaurants and bars. 

West Loop/Fulton Market

BEST FOR FOODIES & MODERN AMENITIES

Pros 

• Home to “Restaurant Row” with a great mix of restaurants
• Vibrant nightlife with plenty of trendy spots
• Quick and easy access to public transport

Cons

• Prices are high, like most central Chicago areas
• Limited green space, with Mary Bartelme Park the main option

The West Loop and Fulton Market have become Chicago’s trendiest neighborhoods, but they weren’t always this polished. Once gritty industrial hubs in the mid-1800s known for meatpacking and manufacturing, they’ve had quite the transformation. Today, historic warehouses are home to offices like Google and McDonald’s, while the streets are packed with award-winning restaurants and stylish boutique hotels.

Highlights include Randolph Street’s “Restaurant Row,” Time Out Market, and a growing mix of upscale bars and shops. The vibe is modern and a little more local, making it ideal for travelers who want a more elevated, less touristy experience while still staying close to central Chicago. It’s also exceptionally well-connected, so you can rely on the CTA to get around rather than driving.

We loved how easy it was to go out at night, and how one dinner plan can easily turn into a few extra stops. If you want to do something other than eat, there’s still plenty going on, from the Randolph Street Market Festival to the National Hellenic Museum and Old St. Patrick’s Church. Not that the West Loop feels busier during the day, but it tends to quiet down in the evening, making it a more relaxed alternative to lively Fulton Market.

Nobu Hotel Chicago – $$$

Nobu Hotel Chicago is where minimalist Japanese design meets the cool industrial vibe of the West Loop. It’s right in Fulton Market and close to “Restaurant Row” on Randolph Street, so some of Chicago’s best restaurants are right on your doorstep.

The hotel itself feels polished but relaxed. You’ve got an indoor pool with an onsen-style feel, separate steam rooms for men and women, and a rooftop area with skyline views that calls your name for one more drink before bed. Downstairs, the Nobu restaurant delivers Japanese-Peruvian food that makes you stop talking for a minute and appreciate every bite.

Rooms are super comfortable, with custom beds, clothes steamers, Dyson hair dryers, yoga mats, and plenty of little touches done properly. The only problem is that it might make you want to stay in rather than explore the city. Prices here start at around $380 and can climb to $800+ USD per night.

If the Nobu Hotel Chicago is all booked up, The Emily Hotel is another fantastic luxury option near the Hubbard Street Murals and Morgan Station. It’s a stylish stay filled with locally made artwork, relaxed hangout spaces, and even a seasonal rooftop movie theatre (which makes for a pretty great date night).

Another one of our top choices here is The Hoxton, Chicago, just steps from vintage markets and art galleries. It stands out for its high-energy social scene, with a rooftop pool that’s a major draw in warmer months, plus a speakeasy with live jazz. 

Hampton Inn Chicago West Loop – $$ 

Hampton Inn Chicago West Loop is one of those rare middle-ground finds, close to the West Loop’s best dining, but without the boutique hotel price tag. It’s also near Union Station, which makes life easier if you’re arriving by train, and just a 10-minute walk from Randolph Street’s restaurant row for anytime dining. 

Fulton Market isn’t exactly cheap, so the free full breakfast here is a nice bonus. There’s also a 24-hour snack shop for late-night cravings or forgotten essentials. The on-site Fulton Tap lets you pour your own craft beer, which also adds a fun twist.

Up top, you’ve got a heated indoor pool and outdoor sun deck with skyline views, the perfect spot to recharge. Prices usually start at $130 per night, depending on your dates.

A stylish alternative nearby is Homewood Suites by Hilton Chicago West Loop, steps from the Fulton Market and Chicago Theatre District. It offers spacious suites with fully equipped kitchens, plus an indoor pool and a terrace that’s perfect for relaxed evenings and sunset views. 

Just a short walk from Willis Tower and the United Center, Hyatt House Chicago West Loop-Fulton Market comes with rooftop skyline views from the pool and terrace. Rooms are some of the biggest in the area, which is always a win, and free breakfast is included, too. 

Level Chicago Fulton Market – $ 

Level Chicago Fulton Market is a great value stay with a five-star feel (not something you come across here too often). That means more space, all-suite accommodation, luxury extras, and a prime location for less than many nearby hotels. It’s also super pet-friendly, with an outdoor dog run and even an indoor pet spa, which isn’t exactly standard for a downtown hotel.

When you’ve had enough of your suite (highly unlikely), head up to the 31st-floor rooftop lounge for panoramic views of the Chicago skyline. And if you’re feeling fancy, you can opt for the penthouse and enjoy views from your own private rooftop hot tub.

The extras keep going here: there’s a spa, fitness center, yoga room, and a heated outdoor pool too! Prices start from around $250 USD per night, which feels like a pretty great deal if you ask us!

Hotel Chicago West Loop is another great option, though much smaller than Level Chicago Fulton Market, set in the Illinois Medical District just blocks from the United Center. What gives it personality is the on-site gallery and mural-covered guest rooms, so if you like a stay with a bit more character, this one’s for you, plus, your furry friend is welcome too. 

Wicker Park & Lincoln Park

BEST FOR A LOCAL, CREATIVE ATMOSPHERE

Pros 

• Wicker Park has an artistic, bohemian, and more youthful vibe with plenty of character
• Easy public transport access to downtown Chicago and O’Hare Airport
• Lively nightlife with a great mix of cafes and bars
• Lincoln Park offers upscale dining and beautiful historic homes

Cons

• Lincoln Park is quieter and generally more expensive
• More common petty crime in Wicker Park compared with quieter areas 
• Wicker Park can be busy and noisy

Wicker Park and Lincoln Park offer a break from downtown, with a more authentic, residential vibe while still giving you plenty to do. Wicker Park is trendy and artsy, filled with vintage shops, live music venues, buzzing Milwaukee Avenue, and colorful street murals. 

Lincoln Park, on the other hand, is quieter and more scenic, with more of an “old money” feel. It’s home to Lincoln Park Zoo, lakefront trails, tree-lined streets, and “Beer Baron Row,” a stretch of impressive 19th-century mansions.

Together, they’re perfect for travelers who want great food, nightlife, and a more local feel without being right in the middle of the tourist core. Both areas are well connected, too, with quick commutes to downtown and O’Hare Airport.

What we love most about Lincoln Park is its huge namesake park, where you’ll find the free Lincoln Park Zoo and the Conservatory. Wicker Park is our favorite neighborhood for late-night cocktails on the weekend.

Just note that these two areas aren’t directly next to each other, but they offer a similar vibe. You also won’t find loads of hotels here, though there are plenty of Airbnbs and apartments, so you’re still well covered.

The Robey – $$$ 

The Robey is housed in the historic Northwest Tower, the only skyscraper in the area, and is the perfect stylish base for exploring Wicker Park. You’ll probably end up spending plenty of time in the cocktail lounge with its rooftop pool and terrace, easily the best spot for drinks before heading out, or for staying in to watch the Chicago skyline glow at golden hour.

If you’re after something moodier, the second-floor lounge with its fun 90s nostalgia vibe is a better fit. You’re also close to Lincoln Park Zoo, Wrigley Field, and just steps from the 606 Trail, with trendy restaurants at your doorstep when you feel like dining out.

Rooms have hardwood floors, factory-style windows, and modern amenities like white noise machines. Many are also adapted for mobility and hearing accessibility. Prices start at around $175 USD per night.

Hyatt Place Chicago Wicker Park – $$

Hyatt Place Chicago Wicker Park is a fantastic mid-range hotel in Wicker Park, near the Salt Shed and The 606 Trail, that perfectly fits its hipster, artsy vibe. With large family rooms, a child-friendly menu, and evening entertainment, it’s a great pick for families who want stylish comfort and fun without the luxury price tag. 

One of the highlights is the rooftop patio with a fireplace (the largest in the area), and a great spot to relax after a day out. You’ve also got free breakfast, a 24-hour fitness center, a coffee shop, and a 24/7 market for snacks, so mornings and late nights are both covered.

The hotel is also well rated for accessibility, with wheelchair-accessible public spaces and elevators, and pets are welcome for an additional fee. With prices starting around $210 USD per night in peak season, we think it’s a solid base for exploring Chicago without blowing the budget.

Hotel Versey Chicago Lincoln Park – $$ 

Hotel Versey Chicago Lincoln Park is a great mid-range choice in the heart of Lincoln Park, surrounded by local diners and close to Lincoln Park Zoo and Wrigley Field. The Diversey Brown/Purple Line “L” station is nearby, so getting into downtown is quick and easy.

What we love most is the quirky decor, with a fun, funky lobby and an upbeat atmosphere that makes you feel like you’re part of something special. Believe it or not, this was once a hangout for legends like Louis Armstrong and Nirvana!

The hotel blends Chicago’s music and art scene, and you can notice it in the little details throughout. It also welcomes pets, which isn’t always common in boutique historic buildings around here. At around $90 USD per night, it feels like a great bargain for a stay with this much personality and history.

The Neighborhood Hotel – $$ 

The Neighborhood Hotel is a small three-bedroom penthouse with a fully equipped kitchen, giving you the freedom to cook and eat on your own schedule. It has a warm, home-like feel that makes it a favorite with groups and families, with space for up to eight guests (great for special occasions).

Inside, you’ll find vintage details and oversized Chicago-themed artwork, including a large photo of Michael Jordan that adds a fun local touch. The whole place feels more like a stylish private home than a typical hotel room, which is exactly what we love about it. You’re also within easy walking distance of Lincoln Park and Lake Michigan.

Just keep in mind there’s a five-story climb, as the historic building has no elevator. Prices start at around $210 USD, depending on your travel dates. Pets are welcome, too, which is always a nice bonus.

Related Read: Turn your stay into a seamless trip with our 3-day Chicago itinerary, covering the city’s must-see spots.

Top Activities to do in Chicago

With your Chicago base sorted, it’s time to get out and experience everything this incredible city has to offer. From iconic eats and skyline views to fascinating history and world-class art, Chicago goes way beyond deep-dish pizza and skyscrapers. These are the tours that seriously elevated our trip!

• Eat your way through Chicago’s classics – This Chicago food tour was such a fun way to dive into the city’s iconic eats, from deep-dish pizza to a classic Chicago-style hot dog and even the original brownie. Between bites, this tour also takes you past top sights like Millennium Park, making it a great mix of food and sightseeing.

• See the skyline from the river – Hands down one of our favorite experiences in Chicago, this architecture river cruise offers unbeatable views of the skyline from the water. With a passionate guide sharing stories along the way, this tour makes the city’s buildings feel even more impressive.

• Take in the views from Willis Tower – This Skydeck tour is a must for first-time visitors, with skip-the-line access and incredible views from 103 floors up. If you’re feeling brave, this tour also gives you the chance to step onto The Ledge for a truly unforgettable moment.

• Step into Chicago’s gangster past – Chicago’s Prohibition-era history really comes to life as you visit real-life crime scenes tied to infamous mobsters on this gangster tour. With a fun, engaging guide, this tour is a unique and entertaining way to see a different side of the city.

• Explore the Art Institute with an expert – This guided Art Institute tour is the best way to experience one of the world’s top museums without feeling overwhelmed. With skip-the-line entry and expert insights, this tour helps you truly appreciate the stories behind the most famous works.

Related Read: Want more ideas? Check out our guide to the best things to do in Chicago here for top experiences and hidden gems.

Thanks for reading!

After busy days in the city, your choice of stay can shape the whole trip. Whether you base yourself in the heart of The Loop, along the Magnificent Mile, or in one of the city’s trendier neighborhoods, each area adds its own vibe. We hope this guide helps you find the perfect fit for your travel style, whether you’re here for the food, the views, the history, or a bit of everything.

Before you lock in your plans, be sure to check out our other USA travel guides here for more tips and ideas. We’ve got plenty of detailed itineraries, foodie spots, and can’t-miss experiences to help you make the most of your time here and beyond. Or scroll through some of our favorites below to start mapping out your next adventure!

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