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Properties in Chicago (and vicinity), Illinois, United States of America. August 20, 2022 through August 22, 2022

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Trip prices include roundtrip flight + stay, taxes, and fees.
2,326 properties
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  1. Stay flexible with a fully refundable property

    We recommend booking a fully refundable stay in case your plans change.
  2. LondonHouse Chicago, Curio Collection by Hilton

  3. Similar to LondonHouse Chicago, Curio Collection by Hilton

  4. Eurostars Magnificent Mile

    Eurostars Magnificent Mile

    River North
    Fully refundable property
    4.2/5Very Good(2,049 reviews)4.2 out of 5 Very Good (2,049 reviews)
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  5. Hyatt Regency Chicago

    Hyatt Regency Chicago

    The Loop
    Fully refundable property
    4.3/5Excellent(3,028 reviews)4.3 out of 5 Excellent (3,028 reviews)
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  6. The Godfrey Hotel Chicago

    The Godfrey Hotel Chicago

    River North
    Fully refundable property
    4.2/5Very Good(1,640 reviews)4.2 out of 5 Very Good (1,640 reviews)
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  7. Congress Plaza Hotel

    Congress Plaza Hotel

    The Loop
    3.7/5Good(4,058 reviews)3.7 out of 5 Good (4,058 reviews)
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  8. Swissotel - Chicago

    Swissotel - Chicago

    Chicago
    Fully refundable property
    4.2/5Very Good(2,311 reviews)4.2 out of 5 Very Good (2,311 reviews)
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  9. 21c Museum Hotel Chicago

    21c Museum Hotel Chicago

    River North
    Fully refundable property
    4.2/5Very Good(844 reviews)4.2 out of 5 Very Good (844 reviews)
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  10. Fairmont Chicago at Millennium Park

    Fairmont Chicago at Millennium Park

    The Loop
    Fully refundable property
    4.2/5Very Good(1,013 reviews)4.2 out of 5 Very Good (1,013 reviews)
    We have 6 left at
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  11. The Whitehall Hotel

    The Whitehall Hotel

    Chicago
    3.9/5Good(3,361 reviews)3.9 out of 5 Good (3,361 reviews)
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  12. Best Western Grant Park Hotel

    Best Western Grant Park Hotel

    The Loop
    3.7/5Good(2,851 reviews)3.7 out of 5 Good (2,851 reviews)
    We have 2 left at
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  13. Kimpton Hotel Monaco Chicago, an IHG Hotel

    Kimpton Hotel Monaco Chicago, an IHG Hotel

    Chicago
    Fully refundable property
    4.7/5Exceptional(1,004 reviews)4.7 out of 5 Exceptional (1,004 reviews)
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  14. InterContinental Chicago Magnificent Mile, an IHG Hotel

    InterContinental Chicago Magnificent Mile, an IHG Hotel

    Magnificent Mile
    Pool
    Fully refundable property
    4.2/5Very Good(1,128 reviews)4.2 out of 5 Very Good (1,128 reviews)
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  15. Found Hotel Chicago River North

    Found Hotel Chicago River North

    River North
    4.1/5Very Good(1,004 reviews)4.1 out of 5 Very Good (1,004 reviews)
    We have 1 left at
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  16. River Hotel

    River Hotel

    The Loop
    4.3/5Excellent(1,868 reviews)4.3 out of 5 Excellent (1,868 reviews)
    We have 4 left at
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  17. Club Quarters Hotel, Central Loop, Chicago

    Club Quarters Hotel, Central Loop, Chicago

    Chicago
    4.2/5Very Good(1,761 reviews)4.2 out of 5 Very Good (1,761 reviews)
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  18. Club Quarters Hotel Wacker at Michigan, Chicago

    Club Quarters Hotel Wacker at Michigan, Chicago

    The Loop
    Fully refundable property
    4.2/5Very Good(1,268 reviews)4.2 out of 5 Very Good (1,268 reviews)
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  19. Hilton Garden Inn Chicago Downtown Riverwalk

    Hilton Garden Inn Chicago Downtown Riverwalk

    Chicago
    Fully refundable property
    4.4/5Excellent(1,411 reviews)4.4 out of 5 Excellent (1,411 reviews)
    We have 3 left at
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  20. Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    Magnificent Mile
    3.8/5Good(1,684 reviews)3.8 out of 5 Good (1,684 reviews)
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  21. Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    Chicago
    4.6/5Wonderful(1,529 reviews)4.6 out of 5 Wonderful (1,529 reviews)
    We have 1 left at
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  22. Radisson Blu Aqua Hotel Chicago

    Radisson Blu Aqua Hotel Chicago

    Chicago
    Pool
    4.1/5Very Good(1,506 reviews)4.1 out of 5 Very Good (1,506 reviews)
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