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A city whose rapid rise to riches spawned a rough – even brutal – reputation, America’s third largest city has long been rehabilitated as the civilised capital of the Mid-West. It now stands as a lakeside cultural and commercial mecca dominating in the wide expanses of America’s rich agricultural and industrial heartlands. The best places to stay in Chicago are ideally situated to make the most of this thriving city, whether you're here for business or pleasure.
Here “cultural” does not just mean symphony orchestras, Picassos and Rembrandts, though Chicago has more than its fair share of those. Chicago culture is American culture in all its guises, highbrow and popular, which is partly why 44 million visitors a year make their way to this city on the shores of Lake Michigan.
The Windy City is the place to experience all-American urban life at its finest, encompassing the dramatically vertical cityscape of the Loop business district (Chicago was home to the first skyscrapers), the clackety El Train system, the cavernous grandeur of Union Station, the Wrigley field baseball stadium, Frank Gehry’s fantastically-shaped Pritzker Pavilion.
Then there’s the distinctive Chicago takes on American food classics:, deep dish pizza, juicy beef sandwiches and their gourmet version of the hot-dog.
And that’s before we consider Chicago’s status as one of America’s street musical powerhouses, the city that began the blues revolution personified by a long list of great names, including Muddy Waters, Howlin’ Wolf and Buddy Guy, whose influence is still strongly felt on a thriving late night club scene.
The writer Nelson Algren summed up Chicago best: ‘Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.’ Here’s our selection of the best places to stay in Chicago to experience that reality in a city that offers everything to the true connoisseurs of American life.
- Arguably the grande dame of Chicago Hotels, The Peninsula is a city landmark. Perfectly situated and towering above an entire city block of the Magnificent Mile, it is famous for its stained-glass wall and gilded lobby ceiling, as well as three award-winning restaurants. The ultimate Chicago stay.
- You can rely on the Canandian-owned Four Seasons group to deliver a superior hotel experience and the Windy City’s Four Seasons is up to the old world-classy mark with its Lake Michigan views, and superior facilities, location, and staff friendliness.
- Housed in a skyscraper designed by the architectural legend Mies vad der Rohe, The Langham offers “British-style” luxury combined with majestic views of the cityscape, the Chicago River, and Lake Michigan. Understated elegance in the heart of this cosmopolitan metropolis.
For arty types
- Dating back to the 1920s, the Hotel LIncoln is a funky vintage-style property set in the Old Town Triangle off Lincoln Park, which showcases original artwork from local artists. Hip contemporary style and a good springboard for exploring the city’s rich artistic offerings.
- Freehand, Chicago. “A relaxed community vibe” distinguishes this home from home in Chicago’s vibrant River North neighbourhood, home to some of the city's best art galleries, boutiques and restaurants. Here you'll find Innovative design, and an offering of affordable shared and private rooms.
- The ACME Hotel is downtown Chicago's alternative lifestyle boutique hotel, created with an eye for design and a high-tech vibe, Hip and trendy, but not forbidding, you are invited to “blow your mind, not your budget.”
- For families, one of the best places to stay in Chicago is the Dana Hotel & Spa. It might not be the cheapest option, but you'll be spoilt for choice in terms of great facilities and the location is ideal to explore the ctiy.
- Hotel Palomar also ticks the family boxes with a great indoor pool, bunk-bed rooms, family friendly dining and even hula hoops in the fitness rooms to keep all ages happy!
- For all carnivores, a good steak is a must and you'll find one of those at The James. This chic property is well situated and boasts David Burke's Primehouse which is regularly voted Chicagos no. 1 steakhouse.
- The Pump room restaurant is one of the reasons to book the Public Chicago. The farm to table style dining offering reasonable priced delicious cuisine in a relaxed atmosphere has been pioneered by award winning chef Jean-George Vongerichten. The Public is also a good choice for the design conscious - this Ian Schrager property will not disappoint.
For a buzzy atmosphere
- Milenorth is a lively property on Magnificent Mile and close to Navy Pier. The bar is popular with residents and locals alike, it's in the heart of Chicago's restaurant and shopping area, and it's great value too!
- The Thompson Chicago is a trendy hotel, again in a great downtown area, which oozes style from every pore. Nico Salone is a great spot for cocktails, dinner or a bit of both, and the locals seem to like it too!
- The Virgin Hotel is all about fun and great hospitality. The Commons Club is a must for cocktails and if you pop in between 7 and 8pm, you'll be able to indulge on the house!
Best Hotels in Chicago
Freehand 217 rooms from $85Chicago (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.Value chic - With doubles from as little as $85 per night (or only $25 per person if you're prepared to share a dorm) it's unbeatable valueGreat walks - Every Saturday morning, the hotel arranges for pay-what-you-like walking tours.Kayaking - Explore Chicago from an unusual angle on a kayaking water tour.Lively area - In the thick of the action.Recommended by - Tablet
Hotel Lincoln 184 rooms from $150Chicago (Illinois)
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.Great walks - Go for a stroll through Lincoln Park which the hotel overlooks.Sights nearby - Wrigley Field is nearby.Lively area - In the thick of the action.Views - Great views from hotel
Public Chicago 285 rooms from $180Chicago (1301 N State St)
Part of the Gold Coast neighborhood, this personal, luxurious and lively hotel caters to all guests' needs while offering prime location in Chicago. Rooms are plush down to the cotton linen count. The Pump Room bar is popular with all and award winning chef Jean-Georges Vongerichten is worth a try.Sights nearby - Willis Tower, John Hancock Centre and the Art Institute of Chicago are all famous in their own right and worth a visit.Great walks - Walks on the Lake Front Trail or through Chicago Park District.Lively area - In the thick of the action.Lively - Hip and happening.
The James 294 rooms from $180Chicago (Illinois)
This flagship chic hotel one block away from Miracle Mile is well finished and a swanky affair in a prime location. Rooms are spacious and plush with spectacular views. Between David Burke's Primehouse steak house and the range of spa treatments it is a fantastic city break spotLively - David Burke's bar is popular with the local Chicago crowd/Views - Higher rooms offering great view of the Chicago cityscape.Sights nearby - Well located for major sights.Romantic - Good for couples.
Chicago Athletic Association 241 rooms from $190Chicago (Illinois)
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.Sights nearby - Millennium Park is in close proximity to the hotel.Lively - Hip and happening.Views - Great views from hotelFull of character
Milenorth 215 rooms from $195Chicago (Illinois)
This boutique, lively hotel on the Magnificent Mile and 5 minutes from Navy Pier is luxury and location in one. Rooms are contemporary modern and airy. The rooftop houses a popular bar and restaurant enjoyed by locals alike. Great spot for a city break with restaurants and shops all around.Sights nearby - Willis Tower and the John Hanncock Centre are worth a visit for spectacular views of Chicago.Lively - Hip and happening.Full of characterOutstanding location
Acme Hotel Company 130 rooms from $229Chicago (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 after work with a craft cocktail.Sights nearby - Willis Tower and John Hancock Observatory to name a few!Quirky - An experience!Recommended by - Tablet
Hotel Palomar, Chicago 261 rooms from $240Chicago (Illinois)
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.24 Hour room serviceViews - Great views from hotelSwimming Pool - Indoor/outdoorSights nearby - Well located for major sights.
Thompson Chicago 247 rooms from $280Chicago (21 E Bellevue Pl)
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.Lively - Salone Nico is a favourite of Chicago bussiness types on an evening.Sights nearby - Buckingham Fountain is a must see, as well as 'The Bean'.Great walks - Grant Park and Lincoln Park are both worth a visit.Views - Either of Lake Michigan or the Chicago skyline.Recommended by - Mr & Mrs Smith, Tablet
Virgin Hotel 250 rooms from $290Chicago (Illinois)
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.Sights nearby - The Willis Tower or John Hanncock Centre - both offer great views of the city.Lively - Bar and entertainment readily avaliable.Spa
Dana Hotel & Spa 216 rooms from $430Chicago (Illinois)
In a prime spot this boutique hotel boasts breathtaking Chicago views from the Vertigo Sky Lounge. Modern, spacious rooms offer mini bar and in-room spa treatments. Enjoy the onsite gym and spa, the global cuisine restaurant and popular bar. A great place for all the family to explore a vibrant cityGreat walks - North Beach, Lincoln Park and along Michigan Lake all offer great locations for a stroll in the city.Sights nearby - Museum of Contemporary Art and Navy Pier are all within walking distance.Local markets - The famous American Girl store is close by.Lively - Hip and happening.
The Peninsula Chicago 339 rooms from $500Chicago (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.Spa - The Peninsula Spa is inspired by Ayurvedic and Asian philosophies, wih massages and therapy treatments to soothe any ailment.Sights nearby - The Museum of Contemporary Art, Driehaus Museum and beloved Chicago Water Tower are all a 5 minute stroll from the Peninsula.Lively area - Located in the Near North area of Downtown Chicago, along the electric Magnificent Mile.Swimming Pool - Indoor pool with views over downtown Chicago's skyline.Recommended by - Tablet
The Langham, Chicago 268 rooms from $550Chicago (Near North Side)
Overlooking the Chicago river and surrounded by down-town 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.Sights nearby - Located right next to the ostentatious and famous Trump Tower and less than a mile from the Museum of Contemporary Art.Kids Club - Fully staffed.Views - Great views from hotelSpa
Four Seasons Chicago 346 rooms from $575Chicago (Gold Coast)
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, jacuzzi, restaurant.Sights nearby - In downtown Chicago there is a multitude of architectural splendour, museums and art galleries in the near vicinity.Views - Panoramic views over Chicago and Lake Michigan.Spa - Body treatments, facial, massages and sauna.Swimming Pool - Indoor pool