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308 Results
  • Palmer House a Hilton House
    Ranked #1 overall in Chicago hotels
    8.9
    Wonderful!
    36 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

    High tea at 3pm ever day..Princess Diana stayed there when in town :-) :-) :-) :-)

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

    You can't beat the location of this hotel, right along the river with great views and a block from Michigan Ave. It has been recently remodeled, with multiple places to ...

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

    A beautiful hotel perfectly situated on Magnificent Mile, allowing you easy access to the Art Institute, shopping and Navy Pier. Also, it is in a way, a piece of art ...

    • 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

    Regal and upscale, The Peninsula is a 5 star hotel all around. Service is excellent and the decor is classical. Their famous afternoon tea in the lobby is lovely. A ...

    • 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

    Big rooms, and they had live music in the bar on a Tuesday night. All staff has been very friendly and helpful. For those of you in the advertising industry, ...

    • 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

    I've stayed at many hotels in Downtown Chicago and this is my favorite! The room was spacious and beautifully decorated and the bed was so comfortable! Trendy but not over-the-top ...

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

    Breezy views of the Lake and Navy Pier along with signature W amenities and a pool make the W Lakeshore a perfect choice for a summer stay.

    • 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

    It was a treat to show up at 5pm while the complimentary wine, beer, and cocktails were being served. They also had some great flatbreads. The service is the best ...

    • 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

    excellent hotel, nice rooms, its one of the best in Chicago.

    • 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

    Hilton Chicago is a typical large scale hotel just slightly off the main downtown area. You seen it in many movies including The Fugitive. The rooms are variable but usually ...

    • 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

    The Park Hyatt has lots of design touches packed into its intimate setting. In addition to its sophisticated interior design, there is also fine art throughout the lobby and the ...

    • 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
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  • Doubletree by Hilton Chicago Magnificent Mile
    Ranked #16 overall in Chicago hotels
    8.6
    Wonderful!
    13 reviews
    Popular withLuxuryNightlifeFoodies

    Super nice and fancy hotel in the center of the city. Great service, beautiful large bedroom with a cool bathroom. Got it pretty cheap through a discount on lastminute.com. Don't ...

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

    Enjoy a cheap sleep and make new friends from all over the world! It's kind of like a Do It Yourself version of MTV's "The Real World". My best Chicago ...

    • Free WiFi
    • Free Breakfast
    ReviewsPhotosAmenitiesMaploadingclose
  • 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
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  • Hotel Lincoln, a Joie de Vivre Hotel
    Ranked #19 overall in Chicago hotels
    8.7
    Wonderful!
    11 reviews
    Popular withHipstersArtsyFamilies

    Just checked into Hotel Lincoln. It's very stylish with friendly staff. It's also centrally located with a trendy bar that draws the whole city.

    • 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

    If you are looking for a place to stay that is within walking distance from prestige retail stores, trendy restaurants, and vibrant nightlife then this hotel is for you. This ...

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

    Beatiful deli Aaaa Friend Family Good Design

    • 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

    The location is amazing, the building is just off of the MagMile. Service is outstanding and rooms comfortable enough for an enjoyable stay.

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

    The staff... impeccable. The grounds... luxe. The rooms... comfortable and posh. It was worth every damn penny spent!!! Seriously, it truly was amazing.

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

    Clean, inviting, family and pet friendly space. Stayed over a week, all the staff were helpful and friendly. Modern minimal feel in the rooms. Quiet enough for being downtown. There ...

    • 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

    Lets start off by saying I travel A LOT(3-4 Different Hotels A Week) When I walk into a hotel I at least expect it to l o o k like ...

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

    Beds were a bit uncomfortable, for some reason. I could not stay asleep for more than 4 hrs at a time both nights I was there. The conference I was ...

    • 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

    I attended an event at the Sears Tower and this hotel was conveniently located a few blocks away. It's trendy and luxurious (as you would expect of a W), and ...

    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • The Blackstone A Renaissance Hotel
    Ranked #28 overall in Chicago hotels
    9.2
    Wonderful!
    10 reviews
    Popular withHistoryArtsyLuxury
    • Restaurant
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Four Seasons Hotel Chicago
    Ranked #29 overall in Chicago hotels
    9.0
    Wonderful!
    10 reviews
    Popular withLuxuryBusinessFamilies

    In a city of four seasons, The Four Seasons Hotel fits right in. Expect luxury throughout the hotel and attention to detail in every room. Catch an incredible view of ...

    • 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

    The first view of Hotel Monaco isn't impressive, but I was happy to see that the inside is nicer looking than the shabby awning outside. Some highlights: animal print robes ...

    • 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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