20 Cool Hotels in Chicago (2025)

Table of Contents

• Searching for serious style? Choose a design-led hotel.
• Love the glitz? Browse our glamorous finds. 
• Want to please everyone? Look at these family-friendly stays.
• Fancy a bit of a buzz? Jump to our lively options.
• Seeking sleek and central? Head to our favourites for city style.
• Impressed by the details? Search these chic boutiques.
• Something extra-special? Spoil yourself with our luxury picks.

Chicago has many draws for a fun city break. Whether you're visiting to catch a sports game, you're here for one of its festivals, or you simply want to soak in the iconic architecture and experience the happening nightlife — there is a lot to keep busy with here. The hotel scene is as dynamic as the city itself. Expect grand and historic buildings converted into stylish boutiques, sleek modern hotels with chic rooftops, and properties that have stand-out bars or restaurants. Our hotel experts have scanned the city to bring you a collection of cool hotels in Chicago selected on their design, amenities, and overall vibe. With something to suit most tastes and budgets, why not browse through our collection to start planning your stay?

For the design

• Adults-only Nobu Hotel Chicago makes a serious style statement with Asian-inspired minimalist furniture and Japanese tubs. Floor-to-ceiling windows frame fantastic city views, plus there's a top-notch restaurant serving Nobu culinary favourites, a sleek indoor pool and a skyline-facing rooftop terrace.
• TheWit Hotel is a playful and buzzy hotel with spacious rooms and luxury creature comforts. Expect high ceilings, large windows with skyline views and bold flashes of colour all around. Dine at the excellent on-site restaurant and enjoy the 27th-floor rooftop bar.

• Picture a historic 1920's facade married to a glorious waved glass tower, with interiors by TAL Studio, and you have Viceroy Chicago. The rooms make a spectacular statement with sleek furnishings and amazing views from the floor-to-ceiling windows. The rooftop bar and pool are the icing on this supercool cake!

For the glamour

• Built-in 1924, Art Deco is the theme at The Allegro Royal Sonesta Chicago Loop. The interiors ooze glamour with a Gatsby-esque cocktail bar and restaurant, plus a huge luxurious lobby. The location is prime theatreland — The Cadillac Palace Theatre is connected to the property and the Chicago Opera is nearby.
• The Talbott Hotel is another glamorous Great Gatsby style hotel, in a beautifully refurbished 1920's building in downtown Chicago. The comfortable and spacious rooms have been carefully crafted by local designers. The popular on-site restaurant draws crowds, as do the cocktails at the vintage bar. An elegant choice.

For a family getaway

• For a fun, relaxed party-like atmosphere the Found Hotel Chicago River North is a great find for families! Expect funky interiors with mismatched colours, multi-layered textures and ethnic prints. The shared dorm-style rooms with cosy multi-level bunk-beds offer great value for money. There's also a games room and karaoke in the property's Asian-inspired lounge.
• Freehand is another good value hotel with a boutique feel in downtown Chicago. Rooms are boho chic and come in various sizes including quads and a penthouse, which sleeps up to six, meaning there are flexible options for families. An affordable and hip choice for those travelling with kids.

• The Neighbourhood Hotel Lincoln Park is close to Lake Michigan’s walking/running path, beaches and countless green spaces. It offers family-friendly suites (1-3 bedroom options), some with fun bunk-beds, plus kitchens and private patios. A cool place to experience Chicago, this is ideal for a reasonably-priced family getaway.
• Expect cool, contemporary city-style near Chicago's river and lakefront at the Loews Chicago. Rooms are sleek and modern with floor-to-ceiling windows to take in the city views. The rooftop bar and steak house are a real lure, while kids are well taken care of with iPads loaded with age-appropriate games, consoles, toys and activity books. Seriously good value for what is a luxury stay.

For a lively stay

• For a bold and buzzy option The Wade is a great pick. Overlooking Lake Michigan, rooms here resemble cruise liner cabins with a stylish mishmash of colours and textures. There's an indoor pool, spa and restaurant, plus it's just a short walk to Ohio Beach for swimming or sunbathing with city views.
• Moxy Chicago Downtown is a buzzing and fun boutique-style hotel. When the reception doubles as a bar you can be sure of a good time! Decor is contemporary industrial-cool, with splashes of hot pink. Rooms aren't huge but have everything you need. The 24-hour taco restaurant is useful after nightly DJ sets. Perfect for party animals.

• Eurostars Magnificent Mile is, as its name suggests, well positioned to access the city's best shopping area. The super sleek rooms boast floor-to-ceiling windows, polished wood floors, and minimalist furniture — the best have windows across two walls. There's a spa and restaurant, plus the roof terrace is a cool place to sip cocktails with the city skyline as a backdrop.

For city style

• Once the tallest building in the city, The Blackstone is a historic grand dame updated to the 21st Century. Expect wood-panelling, chandeliers and double-height ceilings combining with buzzing restaurants, an extensive art collection and quirky modern furniture. Having hosted many Presidents and celebrities, you can be sure of a very trendy crowd.
• Set in a stunning Art Deco building, Pendry Chicago oozes city chic. Rooms in elegant, neutral tones offer stunning views across the city, river and harbour. With a French brasserie and intimate bar for dining and drinks, it's a decadent stay.
• The LaSalle in downtown Chicago's Loop area packs a punch in the style stakes. Bold rooms have high-end finishes, rich tones and opulent bathrooms featuring Art Deco touches. There's also an elegant lobby, top class steakhouse restaurant and an intimate bar. 

For a chic boutique

• Hotel Zachary is a lively boutique hotel opposite Wrigley Field baseball stadium. An industrial conversion masterclass, interiors are cool, contemporary and yet cosy. Dining spaces are the real draw and popular with locals.
• Hotel EMC2 is a funky boutique-style hotel set in Chicago's lakeside neighbourhood. Pick this property for the bold design which includes rooms with Dali-esque murals, glass showers with copper tubing, dark wood floors and bright art. Complete with a lively restaurant and bar — this is a stylish yet fun stay.
• The Gwen has undergone a divine transformation from historic building to luxury boutique hotel. Art Deco glamour reigns supreme in the rooms, restaurants and the chic wrap-around rooftop bar. Expect jewel tones, gold fittings, glossy marble and epic city views. A sexy and stylish stay.

For a luxury escape

• The St Regis Chicago is a sleek and sophisticated choice in downtown Chicago, right where the river meets the lake. Rooms are spacious and elegant with contemporary furnishings and stunning views. There's a luxurious wellness area with a sauna and steam room, plus Italian and Japanese fine dining.
• Chicago Athletic Association was a Gentleman's club in the early 1800s which has now opened its Venetian Gothic doors to all and boasts large, retro rooms with Millennium Park views. Cherry Circle Room catches the essence of its former dining glory while the rooftop bar completes the picture on this old-school-cool stay.

Still not sure where to book?

• Browse our list of the best places to stay in Chicago.
• Check out all our recommendations in Illinois.
• Refine your search and look at the best hotels in West Loop, Chicago, the best hotels with rooftop pools in Chicago, the best five-star hotels in Chicago or the top Chicago hotels with parking.
• Alternatively, you could contact one of our friendly Gurus for personalised advice.