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're visiting simply 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 chic boutiques, sleek modern hotels with rooftop pools, 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?
Chicago (Near North Side)
Among the Chicago Mansions, this lively and trendy hotel offers prime location for Magnificent Mile and lakeside views. Contemporary rooms with noteworthy comfortable beds and waterfall showers, offering room service as well as Nico Osteria restaurant for fine Italian cuisine and wines.
Chicago (Near North Side)
Trendy hostel and hotel offering chic but affordable accommodations in exciting downtown Chicago. Popular and busy bar serves craft cocktails and light meals. Rooms are hip with a boutique appeal, high-quality furniture in dark woods, walls decorated with crafts and an effortlessly cool vibe.
Chicago (The Loop)
Gentleman's club in the early 1800s now opens its Venetian Gothic doors to business travellers, leisure seekers and city slickers. Large, retro rooms boasting Millennium Park views. Cherry Circle Room catches the essence of its former dining purpose. Remember the bar up on Cindy's Roof Top Terrace.
Chicago (Wicker Park)
Situated in Chicago's Wicker Park, The Robey is set in the art-deco former Northwest Tower building and provides boutique, upmarket accommodation. Expect fresh and contemporary design. Café Robey serves up French-American fusion cuisine and cocktails are served on the rooftop lounge. Superb!
Chicago (West Loop)
A boutique B&B offering hip design in the trendy West Loop. Featuring a heaving library and author-themed rooms with books to match. A home-cooked breakfast feast is provided for each guest and there's a round-the-clock pantry. A charming and central base to explore the city from.
Chicago (The Loop)
An iconic and elegant building in the Loop's financial corridor. Named for its grey marble exterior, the rooms mirror this toned down grandeur, with the odd splash of colour and quirky design. With a range of bars and restaurants, and excellent 24 hour gym they have all the bases covered.
Chicago (Near North Side)
A 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 spot.
Chicago (Fulton Market)
A high-end luxury hotel in easy reach of the city centre and Chicago’s best nightlife spots, ideally designed and equipped for business or pleasure. Public spaces and rooms are bright and elegant, making excellent use of space, and the rooftop pool and range of restaurants won't fail to impress.
Chicago (Near North Side)
Cool, contemporary city style near Chicago's river and lake front. Spacious and grown-up rooms blend a luxury palette of charcoal and silver hues, with enormous windows. Take in lake views from the rooftop bar after a great steak at the restaurant. There's a large pool and welcoming lobby lounge.
Chicago (Near North Side)
Funky boutique-style hotel located in Chicago's lakeside neighbourhood. Rooms are contemporary luxury with a twist; think Dali-esque murals, glass showers with copper tubing, dark wood floors & colourful art. The double-height restaurant and bar are buzzing. Fun and comfort in equal measure.
Chicago (The Loop)
Historic grand-dame updated for the 21st-century. Built in the Beaux-Art era, this city-centre luxury hotel is the epitome of boutique glamour. Wood-panelling, chandeliers & double-height ceilings combine with buzzing restaurants, extensive art collection & quirky modern furniture to great effect.
Chicago (Near North Side)
Divine transformation from a historic building to a luxury boutique hotel. 1920s sculptor Gwen Lux is behind the façade; Art Deco glamour reigns supreme in the rooms, restaurants & a wrap-around rooftop bar. Expect jewel tones, gold fittings, glossy marble & epic city views. A sexy & stylish stay.
Chicago (Andersonville)
Fantastically fully-equipped one, two & three-bedroom self-catered apartments in Chicago's Anderson district. Each of the fresh, lofty and spacious units provides everything expected from a lovely home; dishwashers, driers, gym, balconies & even a roof terrace. A comfortable option for long stays.
Chicago (Lakeview)
Lively boutique hotel opposite Wrigley Field baseball stadium. An industrial conversion masterclass, interiors are cool, contemporary and yet cosy; expect a sophisticated grey palette with fun baseball-themed touches & large-scale artworks. Dining spaces are the real draw and popular with locals.
Chicago (Near North Side)
Buzzing and fun boutique-style hotel. The reception doubles as a bar; expect cocktails on arrival. 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.
Chicago (The Loop)
Bright lights in the big city. Playful and buzzing 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. The 27th-floor rooftop bar is a reason to stay in itself.
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