A cultural and commercial hotspot with a fabulous foodie scene and vibrant nightlife, ‘The Windy City’ is a deservedly popular year-round destination for travellers of all ages. Accommodation options range from cosy B&Bs to indulgent luxury hotels, fit for a whole host of tastes and budgets. Our selection of the best places to stay in Chicago promises hip design, proximity to lively eateries, galleries, museums and event venues, and a very warm welcome. If you're not sure where to base yourself, check out our guide to Where to stay in Chicago, which explains the pros and cons of the best neighbourhoods.
Synonymous with unabashed all-American culture, Chicago receives 44 million visitors a year — eager to savour deep-dish pizzas, peanut-butter-and-banana-topped waffles and gourmet hot dogs whilst listening to innovative street music or catching a glittering gig in Millennium Park. Visit the Field Museum, the Museum of Science and the Art Institute of Chicago, marvel at Frank Lloyd Wright’s builds and stroll along streets punctuated by public artworks. Frank Gehry’s fantastically-shaped Pritzker Pavilion and grand Union Station are also amongst the city’s many architectural attractions. Walking tours of the city are a marvellous way to delve into food, art and history as a family, couple or group. Head to the 360° Chicago Observation Deck to take it all in from afar.
Spend your evenings soaking up Chicago’s blue scene, cheering with the crowds at Wrigley Field, hearing the Chicago Symphony Orchestra or partying at one of Millennium Park’s many festivals. Busy, brash and buzzing, Chicago is one of the USA’s most iconic cities. Rooms at the best places to stay in Chicago fill up fast — book well in advance to experience this American metropolis for yourself!
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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 (Near North Side)
Wes Anderson-style exterior combines with funky interiors; all mismatched colours, multi-layered textures & ethnic prints. Well-designed rooms are basic but very comfortable and either private or shared; the latter dorm-style with cosy multi-level bunk-beds. Idulge in late-night revelry at the bar.
Chicago (The Loop)
Fun and great-value luxury hotel for those who don't take themselves too seriously. Iron filigree staircases, endless ceilings and exquisite tiled floors combine with contemporary style in pineapple-themed rooms; expect pet-friendly touches & fluffy duvets. The superb restaurant is a city favourite.
Chicago (Lincoln Park)
A charming hotel in the Lincoln Park district, close to Fullerton Beach. Stylish, comfy suites in a soft colour palette with a mix of old and new furnishings; each has its own kitchen and some have a private patio. There are plenty of restaurants on the doorstep. A cool place to experience Chicago.
Chicago (Logan Square)
Excellent farm-to-table restaurant with rooms. The buzzing dining room channels a traditional Chicago inn with plenty of local charm. Each authentic room is different but features wooden floors, exposed brick walls and fun artwork. Will appeal to those keen to avoid cookie-cutter city hotels.
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)
Affordable romance in the heart of the city. Well-designed contemporary rooms have Art Deco and Mid-century touches and killer views. Buzzing public areas combine exposed brickwork, mismatched furniture and playful lighting to create fun and welcoming spaces. Stay here after a night on the town.
Chicago (The Loop)
Glossy modern minimalism meets historic glamour in this jewellery box of a hotel. The 19th-century building has benefited from a star-chitect redesign and reflects the area's heritage. Expect pearl and gemstone hues, high ceilings, marble floors and period-style pillars. Great value boutique chic.
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 (Near North Side)
Boutique luxury for those on a budget. Inviting public areas are a stylish mishmash of textures, textiles and tones with mid-century funiture. Muted rooms are designed to feel like home with cosy throws, Netflix, spa showers and eclectic artwork. There's a spa & beautiful French bistro-style bar.
Chicago (Wicker Park)
Contemporary, bold and boutique rooms in Wicker Park. The unqiue decor mixes patterned curtains & brightly coloured walls with fun vintage-style furniture. Perfect for those who want to experience Chicago daily life but from a luxurious base. There is a shared kitchen but it's more fun to eat out.
Chicago (Near North Side)
Hip hotel with boutique-appeal and sophisticated rooms overlooking the skyscrapers of down-town Chicago. Rooms are sleek and monochrome with splashes of colour and kitted out in gadgetry galore. The Berkshire Room bar is a trendy spot for young Chicagoans to unwind with a craft cocktail.
Chicago (Lincoln Park)
On the north side of Chicago opposite Lincoln Park rests the newly renovated Hotel Lincoln. Rooms are mostly lake facing with local art works and all facilities. This fun-loving hotel houses the farm-to-fork Perennial Virant restaurant and a rooftop bar for stunning views. Great spot to explore.
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)
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 (Old Town)
Boutique B&B in the Old Town. Immaculate light-filled rooms are serene yet homely with soft monochrome colour schemes, fluffy carpets and walk-in showers. A dreamy country-kitchen with relaxed benches, roof-top with city views and fire-side sitting rooms seal the deal. Cosy contemporary love nest.
Chicago (Lincoln Park)
Italian-themed B&B in a leafy residential neighbourhood. Built in the 1880s, expect high ceilings, wooden pillars and Georgian windows. Spacious suites channel a Mediterranean feel with marble baths, Roman busts and antique beds. Relax by the fire or soak in the outdoor hot tub. Made for couples.
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 (The Loop)
A luxury hotel, in downtown Chicago, on Michigan Avenue. Rooms are modern and spacious with marble showers and floor-to-ceiling windows facing the Chicago River. Enjoy a handcrafted cocktail on the sophisticated rooftop bar and delicious seafood and steaks at the restaurant. A spoiling central stay.
Chicago (The Loop)
Contemporary and sleek self-contained apartments situated in the cultural neighbourhood of South Loop. Apartments have kitchenettes, comfortable seating areas and modern bathrooms. Enjoy the breathtaking views from the roof patio (complete with BBQ). A conveniently placed home-away-from-home.
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 (Wicker Park)
Historic charm meets boutique style in a residential neighbourhood. The mix of guest rooms and fully-functioning apartments can also be booked out exclusively. Decor combines antique fireplaces, exposed brick walls, jewel tones & wallpaper accents. The friendly atmosphere works well for long stays.
Chicago (The Loop)
Boutique business hotel with lots of soul. Located in a former hat factory, there are fun historical touches throughout. Bedrooms are classic contemporary luxury; highlights include snug window seats, modern art and a cool but cosy grey and blue palette. Great value and the service is excellent.
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 (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 (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 (Hyde Park)
A contemporary yet cosy boutique hotel located in Chicago's culturally-rich Hyde Park district. Whether you want to feel the city's pulse, see the sites or dine like a local, this impressive hotel is a winner. Decor is eclectic, fun and warm with fantastic artwork. Rooms have phenomenal city views.
Chicago (Near North Side)
Sleek luxury located in a striking futuristic city tower. Light-filled rooms feel like homely enclaves while public spaces evoke Chicago's iconic skyscrapers; the lobby resembles a space shuttle. Decor blends blonde wood with contemporary prints. Dine at the French restaurant - very chic.
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.
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)
Contemporary boutique in central Chicago. There's a gym, yoga classes, restaurant and great rooftop bar that's popular with locals in summer months. Rooms & suites are a playful take on classic luxury, with distinct jewel-tone furniture, modern artwork and deep soaking tubs.
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 (Oak Park)
A small yet sophisticated and stylish B&B located in Oak Park, a leafy village within the Chicago municipality. 5 rooms and suites have been lovingly designed and decorated; expect antique beds, exotic patterned rugs, burning fires and atmospheric slanting ceilings. Many dining options are nearby.
Chicago (Near North Side)
Not only does this hotel have an excellent central location, but it's one of a handful of American properties situated within a museum; the collection is dedicated to 21st century art. Modern rooms and suites manage to feel boutique in style despite the key count with wood panelling and great views.
Chicago (West Loop)
Sexy city style meets world-class cuisine on Chicago's 'restaurant row'. Rooms are a masterclass in luxurious restraint; think 'wow' floor-to-ceiling views, Japanese tubs and Asian-inspired minimalist furniture. Enjoy Nobu culinary favourites, slick indoor pool and skyline-facing rooftop terrace.
Chicago (Near North Side)
A magnificent hybrid of old and new, a perfectly preserved 1920's facade attached to a glistening glass tower. Inside you will find the same paradoxes, the rooms are spectacular and so are the views from their floor to ceiling windows. The rooftop bar draws a crowd, as does The Somerset downstairs.
Chicago (The Loop)
Beautiful hotel set in iconic Art Deco building in downtown Chicago. Elegant rooms feature neutral tones and plush soft furnishings, some with fireplaces, parquet flooring and views across the city, river and harbour. French brasserie and intimate bar for dining and drinks. A decadent city stay.
Chicago (The Loop)
Large in scale but boutique in style with fab facilities. Built-in 1924, Art Deco is the theme, especially in the buzzing Gatsby-esque cocktail bar & restaurant. The expansive luxurious lobby sets the tone while rooms feel like the inside of a jewellery box with lacquered wood and gold touches.
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 (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 (Near North Side)
A contemporary hotel located in the heart of the city in the River North district. Sleek rooms boast floor-to-ceiling windows, polished wood floors, and minimalist furniture. The best have windows across two walls. Complete with a trendy restaurant and bar, plus a spa. A smart downtown stay.
Chicago (Near North Side)
This boutique hotel in the River North district offers an indoor pool, in-room spa treatments, restaurant and popular bar. Rooms are modern with designer bathroom features. Business and fitness centres on site. Proximity to Navy Pier, Michigan Lake and Chicago's landmarks and galleries.
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 (The Loop)
Perfect for the modern traveller or business getaway in Downtown Chicago. Two-chamber rooms with all the mod-cons are contemporary and luxurious. With five restaurants on site there is much choice, as well as the spa and fitness centre. Location is perfect for theatre, shopping and food lovers.
Chicago (The Loop)
A stylish hotel in downtown Chicago's Loop area. Bold rooms have high-end finishes, rich tones and opulent bathrooms featuring Art Deco touches. There's an elegant lobby, top-notch restaurant with steak tasting menu and an intimate bar. Quiet yet close to the action for a sophisticated city stay.
Chicago (Near North Side)
Work hard and party harder. Bold business hotel overlooking Lake Michigan. Rooms resemble cruise liner cabins with impressive views and a stylish mishmash of colours & textures. An indoor pool, spa, yoga classes, buzzing restaurant and a helpful concierge helps make the most of downtime.
Chicago (Near North Side)
Luxury urban resort spread between the 12th & 30th floors of a Lake Michigan tower. Serene rooms feel like you're floating in the sky with phenomenal views and cloud-like beds. Enjoy the Italian steakhouse, spa, indoor pool, and a very cool rooftop bar. Classic contemporary city luxury, a safe bet.
Chicago (Near North Side)
The Peninsula exudes dignified grandeur. Rooms feature touches of high-class elegance such as Bernaudaud china, soaking tubs in bathrooms and specially commissioned art. Impeccable views of glittering downtown Chicago from most rooms and suites. Pool, gym, spa, three award-winning restaurants.
Chicago (Near North Side)
Overlooking the Chicago River and surrounded by downtown Chi-town skyscrapers, this hotel is a glamorous choice for the discerning traveller. Rooms feature a cream canvas, dark polished woods and royal purple throws. Gym, spa, pool. Exclusive private members' club with city views. Restaurant, bar.
Chicago (Near North Side)
All rooms and suites are stylishly furnished with French furniture, floral motifs, art adorning the walls, and shades of plum, champagne, rose and dove grey. Beautiful views over Chicago or Lake Michigan. Spectacular indoor pool under a domed skylight. Gym, full-service spa, hot tub, restaurant.
