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308 Results
  • Palmer House a Hilton House
    Ranked #1 overall in Chicago hotels
    8.9
    Wonderful!
    37 reviews
    Popular withArtsyHistoryLuxury

    Positive impressions so far. This is a huge hotel with great intricate details.

    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Airport Transfer
    • Pets Allowed
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  • The Drake, A Hilton Hotel
    Ranked #2 overall in Chicago hotels
    8.9
    Wonderful!
    32 reviews
    Popular withHistoryLuxuryArtsy

    Very famous and old historic hotels. Rooms above the 5th floor have updated bathrooms. Below the 5th floor it can be a hit or miss. However, the staff is impeccable. ...

    • Fitness Center
    • Pets Allowed
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  • Hyatt Regency Chicago
    Ranked #3 overall in Chicago hotels
    8.1
    Wonderful!
    36 reviews
    Popular withBusinessLuxuryFamilies

    Decent, but outdated ... When we first arrived I noticed that the shower smelled a bit mildewy. Other than that the room sizes were average. I did however love the ...

    • Free WiFi
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • InterContinental Chicago Magnificent Mile
    Ranked #4 overall in Chicago hotels
    8.9
    Wonderful!
    28 reviews
    Popular withLuxuryBusinessAdventure

    What a unique place to stay. My grand children loved the Art Deco pool where Johnny Weis muller trained in the thirties,

    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • The Peninsula Chicago
    Ranked #5 overall in Chicago hotels
    9.4
    Wonderful!
    23 reviews
    Popular withLuxuryBusinessFoodies

    What is not to love about high tea at this hotel. Very attentive service and the food, especially the desserts, were fabulous. My only gripe is that the scones were ...

    • Free WiFi
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • Hard Rock Hotel Chicago
    Ranked #6 overall in Chicago hotels
    8.7
    Wonderful!
    21 reviews
    Popular withBusinessNightlifeLuxury

    Definitely not your typical Hard Rock. Very central to the business district. Great food in the surrounding area, and you are bordered by two Starbucks!

    • Fitness Center
    • Pets Allowed
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  • theWit - A DoubleTree by Hilton
    Ranked #7 overall in Chicago hotels
    9.6
    Wonderful!
    18 reviews
    Popular withHipstersBusinessNightlife

    Hip new hotel in the heart of the Loop! Right next door to the beautiful Chicago Theatre and all the fabulous shopping on State Street. Indoor/outdoor lounge on the 27th ...

    • Restaurant
    • Fitness Center
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  • W Chicago - Lakeshore
    Ranked #8 overall in Chicago hotels
    8.2
    Wonderful!
    19 reviews
    Popular withHipstersLuxuryNightlife

    You can tell it's an older hotel but the rooms are a decent size. The lobby was really busy the whole weekend we were there. The showers in the bathroom ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • Kimpton Hotel Palomar Chicago
    Ranked #9 overall in Chicago hotels
    8.9
    Wonderful!
    16 reviews
    Popular withBusinessLuxuryArtsy

    Tucked right smack dab in the middle of great shopping, dining, and all the color Chicago has to offer, The Palomar is a comfortable and welcoming boutique hotel. The lap ...

    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • The James Chicago
    Ranked #10 overall in Chicago hotels
    9.7
    Wonderful!
    14 reviews
    Popular withLuxuryHipstersNightlife

    The best kept secret of River North, JIMMY is a cocktail bar connected to and operated by the James Hotel, and upscale boutique hotel just off of Michigan Avenue. With ...

    • Free WiFi
    • Fitness Center
    • Pets Allowed
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  • Sofitel Chicago Magnificent Mile
    Ranked #11 overall in Chicago hotels
    9.5
    Wonderful!
    13 reviews
    Popular withFamiliesLuxuryNightlife

    Everything about the Sofitel is focused towards pure luxury and class. The rooms are sterile-clean and the service follows suit. I had a great time here. They have a neat ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Pets Allowed
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  • Hilton Chicago
    Ranked #12 overall in Chicago hotels
    8.4
    Wonderful!
    16 reviews
    Popular withLuxuryBusinessFamilies

    Loved the Hilton Chicago. It's a very huge and historical hotel. Perfectly located in the south loop. Michigan Av is right outside the door to access the Magnificent Mile. Lastly, ...

    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • Park Hyatt Chicago
    Ranked #13 overall in Chicago hotels
    9.3
    Wonderful!
    12 reviews
    Popular withLuxuryArtsyBusiness

    Great on my business trips to windy city

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • Millennium Knickerbocker Hotel Chicago
    Ranked #14 overall in Chicago hotels
    8.1
    Wonderful!
    14 reviews
    Popular withBusinessLuxuryHistory

    don't be fooled by the age of the lobby, front desk, and elevators, because those are misrepresentations of the rooms! rooms are newly renovated with modern decor. nice flat screen ...

    • Free WiFi
    • Restaurant
    • Fitness Center
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  • Swissotel Chicago
    Ranked #15 overall in Chicago hotels
    7.9
    Pretty good
    16 reviews
    Popular withBusinessHipstersAdventure

    When I saw the front of this hotel I was really impressed. The mood is modern European. It is like being at a giant street café, except for the restaurant ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Doubletree by Hilton Chicago Magnificent Mile
    Ranked #16 overall in Chicago hotels
    8.6
    Wonderful!
    13 reviews
    Popular withLuxuryNightlifeFoodies

    I love the Doubletree! The staff was so friendly and accommodating. There is a large, beautiful bar in the lobby with plenty of seating, and off of the lobby there ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Hostelling International Chicago
    Ranked #17 overall in Chicago hotels
    8.8
    Wonderful!
    12 reviews
    Popular withBackpackersStudentsHipsters

    This is my first time to stay in a hostel. The staff, from the reception desk until my departure, were very friendly and helpful. My room was a private room ...

    • Free WiFi
    • Free Breakfast
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  • Omni Chicago Hotel
    Ranked #18 overall in Chicago hotels
    8.7
    Wonderful!
    12 reviews
    Popular withFoodiesBusinessAdventure

    Although the Omni is always a great choice, for some reason the bf felt like it would also be haunted. It wasn't. It was simply a fantastic hotel in a ...

    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Hotel Lincoln, a Joie de Vivre Hotel
    Ranked #19 overall in Chicago hotels
    8.7
    Wonderful!
    11 reviews
    Popular withHipstersArtsyFamilies

    Maybe you don't want to stay in the thick of downtown or can't find a room... Hotel Lincoln is a good solution for you because it is just a short ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Chicago Marriott Downtown Magnificent Mile
    Ranked #20 overall in Chicago hotels
    8.5
    Wonderful!
    12 reviews
    Popular withBusinessHipstersLuxury

    When I walked into the Marriot lobby, I thought I was going to going to be sucked into a portal to dimension X by the mesmerizing vortex in the middle ...

    • Free WiFi
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Hotel Felix
    Ranked #21 overall in Chicago hotels
    8.9
    Wonderful!
    11 reviews
    Popular withArtsyGreenHipsters

    Great overall hotel, very modern and progressive indoor design. The hotel restaurant is also very good.

    • Free WiFi
    • Restaurant
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Cambria Hotel & Suites Chicago Magnificent Mile
    Ranked #22 overall in Chicago hotels
    8.7
    Wonderful!
    11 reviews
    Popular withHipstersLuxuryBusiness

    Great location. Very close to the magnificent mile and next to the legendary pizza spot.

    • Free WiFi
    • Restaurant
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Waldorf Astoria Chicago
    Ranked #23 overall in Chicago hotels
    9.2
    Wonderful!
    10 reviews
    Popular withLuxuryBusinessArtsy

    I stayed at the Elysian on a business trip recently and it was superb. The rooms were large, spacious and beautifully equipped for every business purpose in the book -- ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Radisson Blu Aqua Hotel
    Ranked #24 overall in Chicago hotels
    8.9
    Wonderful!
    11 reviews
    Popular withBusinessLuxuryArtsy

    Awesome hotel, great view, of the Chicago area. Wonderful staff, lovely architecture.

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Congress Plaza Hotel
    Ranked #25 overall in Chicago hotels
    6.6
    Pretty good
    19 reviews
    Popular withHistoryStudentsLuxury

    I thought the staff were a little on the rude side. I like the view but other then that I can't say much about it.

    • Free WiFi
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Sheraton Grand Chicago
    Ranked #26 overall in Chicago hotels
    7.6
    Pretty good
    14 reviews
    Popular withBusinessFamiliesNightlife

    Great hotel in a perfect location just off the river and right next to the Magnificent Mile.

    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • W Chicago - City Center
    Ranked #27 overall in Chicago hotels
    7.7
    Pretty good
    13 reviews
    Popular withHipstersBusinessWellness

    The views out the window of my room were fabulous. Be sure to visit the rooftop restaurant which carries late hours for cocktails and small bites. Had a really great ...

    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • The Blackstone A Renaissance Hotel
    Ranked #28 overall in Chicago hotels
    9.2
    Wonderful!
    10 reviews
    Popular withHistoryArtsyLuxury

    This is a porthole window, overlooking Michigan Avenue, from the Sky penthouse suite at The Blackstone.

    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Four Seasons Hotel Chicago
    Ranked #29 overall in Chicago hotels
    9.0
    Wonderful!
    10 reviews
    Popular withLuxuryBusinessFamilies

    Great location. Friendly and accommodating staff. What you would expect from the Four Seasons. lounge was nice spot for drinks. The brunch special is something to try if you're hungry ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Kimpton Hotel Monaco Chicago
    Ranked #30 overall in Chicago hotels
    9.1
    Wonderful!
    9 reviews
    Popular withBusinessArtsyNightlife

    I stayed here for a couple nights a while back and I was not as impressed as I thought I would be. Although it is very nice and the view ...

    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose

Chicago Hotels

Home of blues and jazz, the inspiration for the famous musical and with a reputation for being slightly breezy at times, Chicago is an exciting American city and a mix of metropolitan luxury and Midwest affability.

Chicago hotels range from the Raffaello Hotel with its roof-top sundeck on the Magnificent Mile, to Downtown Hotel 71 with panoramic river views. Historic Willows Hotel in the Lakeview neighbourhood is a great one for families with nice breakfasts and Wi-Fi while the Chicago Hostel is a great budget choice in The Loop area of the city, for travellers. Trump international Hotel and the beautiful Hotel Burnham are there if you have spare cash burning a hole in your wallet!

If you hire a car in Chicago you could explore nearby Indiana or Illinois but don’t go until you’ve moseyed around Lincoln Park, listened to live music in the Empty Bottle, been to a musical in the Broadway Chicago Theatre and listened to jazz and blues in the House of Blues. Learn more of the history of this musical genre in the fabulous Willie Dixon's Blues Heaven Foundation. Don’t forget to try the famous and ultimate Chicago contribution to world cuisine; the deep dish pizza! It’s messy to eat and definitely not diet food or the Italian beef sandwich of Chicago hot dog.

Book flights to Chicago to shop in independent bookstores and wonderful markets, bike the scenic outdoor Lakefront trails, watch the Chicago Bulls play basketball, skate in Midway Park or bask on the beaches of breath-taking Lake Michigan. With ethnic neighbourhoods, an African heritage and all-American culture, Chicago is as diverse a city as any out there.

If you need flights to Chicago airport Skyscanner can find you the lowest prices by searching hundreds of airlines and routes. If you want flights from Chicago airport why not search 'everywhere' and be inspired to travel somewhere new or search by date, month or even the whole year to find your ideal destination with Skyscanner's fast, free and flexible search.

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