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  1. InterContinental Chicago Magnificent Mile

    Magnificent Mile
    Free Cancellation
    4.3 out of 5 Excellent (1,054 reviews)
    Price is $199
    per night
    $249 total
    Includes taxes & fees
    More information about InterContinental Chicago Magnificent Mile, Opens in a new window
  2. The Peninsula Chicago

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.9 out of 5 Exceptional (1,000 reviews)
    We have 3 left at
    Price is $450
    per night
    $528 total
    Includes taxes & fees
    More information about The Peninsula Chicago, Opens in a new window
  3. The Whitehall Hotel

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.0 out of 5 Very Good (3,137 reviews)
    15% off
    Price was $89Price is now $76
    per night
    $89 total
    Includes taxes & fees
    More information about The Whitehall Hotel, Opens in a new window
  4. Trump International Hotel & Tower Chicago

    River North
    Free Cancellation
    Reserve now, pay later
    4.8 out of 5 Exceptional (1,530 reviews)
    Price is $445
    per night
    $522 total
    Includes taxes & fees
    More information about Trump International Hotel & Tower Chicago, Opens in a new window
  5. Royal Sonesta Chicago Riverfront

    The Loop
    Free Cancellation
    Reserve now, pay later
    4.3 out of 5 Excellent (2,428 reviews)
    We have 6 left at
    Price is $149
    per night
    $175 total
    Includes taxes & fees
    More information about Royal Sonesta Chicago Riverfront, Opens in a new window
  6. Radisson Blu Aqua Hotel Chicago

    Chicago
    4.4 out of 5 Excellent (1,532 reviews)
    Price is $144
    per night
    $198 total
    Includes taxes & fees
    More information about Radisson Blu Aqua Hotel Chicago, Opens in a new window
  7. Hyatt Centric Chicago Magnificent Mile

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.5 out of 5 Wonderful (1,362 reviews)
    Price is $179
    per night
    $210 total
    Includes taxes & fees
    More information about Hyatt Centric Chicago Magnificent Mile, Opens in a new window
  8. The Allegro Royal Sonesta Hotel

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.3 out of 5 Excellent (1,031 reviews)
    Price is $129
    per night
    $151 total
    Includes taxes & fees
    More information about The Allegro Royal Sonesta Hotel, Opens in a new window
  9. Royal Sonesta Chicago River North

    River North
    Free Cancellation
    Reserve now, pay later
    4.6 out of 5 Wonderful (1,000 reviews)
    Price is $149
    per night
    $175 total
    Includes taxes & fees
    More information about Royal Sonesta Chicago River North, Opens in a new window
  10. Sofitel Chicago Magnificent Mile

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.6 out of 5 Wonderful (1,781 reviews)
    Price is $170
    per night
    $223 total
    Includes taxes & fees
    More information about Sofitel Chicago Magnificent Mile, Opens in a new window
  11. Eurostars Magnificent Mile, previously Dana Hotel

    River North
    Free Cancellation
    Reserve now, pay later
    4.4 out of 5 Excellent (1,900 reviews)
    Price is $145
    per night
    $170 total
    Includes taxes & fees
    More information about Eurostars Magnificent Mile, previously Dana Hotel, Opens in a new window
  12. Kimpton Hotel Monaco Chicago

    The Loop
    Free Cancellation
    Reserve now, pay later
    4.6 out of 5 Wonderful (1,001 reviews)
    5% off
    Price was $158Price is now $149
    per night
    $175 total
    Includes taxes & fees
    More information about Kimpton Hotel Monaco Chicago, Opens in a new window
  13. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

    River North
    Free Cancellation
    4.6 out of 5 Wonderful (998 reviews)
    We have 5 left at
    Price is $239
    per night
    $281 total
    Includes taxes & fees
    More information about The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago, Opens in a new window
  14. Swissotel - Chicago

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.3 out of 5 Excellent (1,885 reviews)
    We have 6 left at 10% off at
    Price was $169Price is now $152
    per night
    $199 total
    Includes taxes & fees
    More information about Swissotel - Chicago, Opens in a new window
  15. Hotel Chicago Downtown, Autograph Collection

    River North
    Free Cancellation
    Reserve now, pay later
    4.4 out of 5 Excellent (1,002 reviews)
    We have 5 left at
    Price is $135
    per night
    $158 total
    Includes taxes & fees
    More information about Hotel Chicago Downtown, Autograph Collection, Opens in a new window
  16. 21c Museum Hotel Chicago - MGallery

    River North
    Free Cancellation
    Reserve now, pay later
    4.5 out of 5 Wonderful (82 reviews)
    Price is $131
    per night
    $177 total
    Includes taxes & fees
    More information about 21c Museum Hotel Chicago - MGallery, Opens in a new window
  17. Staypineapple, An Iconic Hotel, The Loop

    Chicago
    Free Cancellation
    4.6 out of 5 Wonderful (1,001 reviews)
    We have 1 left at 26% off at
    Price was $152Price is now $112
    per night
    $149 total
    Includes taxes & fees
    More information about Staypineapple, An Iconic Hotel, The Loop, Opens in a new window
  18. The Drake

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.1 out of 5 Very Good (1,003 reviews)
    Price is $133
    per night
    $156 total
    Includes taxes & fees
    More information about The Drake, Opens in a new window
  19. theWit Chicago - a DoubleTree by Hilton Hotel

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.5 out of 5 Wonderful (1,003 reviews)
    We have 2 left at
    Price is $169
    per night
    $199 total
    Includes taxes & fees
    More information about theWit Chicago - a DoubleTree by Hilton Hotel, Opens in a new window
  20. Waldorf Astoria Chicago

    Chicago
    Free Cancellation
    Reserve now, pay later
    4.7 out of 5 Exceptional (1,003 reviews)
    We have 8 left at
    Price is $425
    per night
    $499 total
    Includes taxes & fees
    More information about Waldorf Astoria Chicago, Opens in a new window