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A residential street with houses, a person walking, and lush greenery.

Galewood Vacations from $345

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The Latest Galewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Oct 15 - Oct 18

    Travelodge by Wyndham Downtown Chicago + Flight

    Downtown Chicago
    3 nights
    2.0 star property
    7.6/10 - Good (2,731 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $641
    $345
    per traveler
    found 1 day ago
    Travelodge by Wyndham Downtown Chicago
  • Front of property
    Sep 13 - Sep 19

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.4/10 - Exceptional (4,935 reviews)
    "Great breakfast"
    Reviewed August 6, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $3,249
    $1,807
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view
    Sep 13 - Sep 19

    Four Seasons Hotel Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.4/10 - Exceptional (1,005 reviews)
    "Late on room service. Forgot items requested, making room service even later. Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working. Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view. Also the wings from room service could be SOO muchh..."
    Reviewed August 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $4,717
    $2,732
    per traveler
    found 1 day ago
    Four Seasons Hotel Chicago
  • Full-size fridge, microwave, oven, stovetop
    Sep 13 - Sep 19

    Level Chicago – Old Town + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.0/10 - Wonderful (512 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $2,426
    $1,501
    per traveler
    found 1 day ago
    Level Chicago – Old Town
  • City view from property
    Oct 15 - Oct 18

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very Good (2,910 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $747
    $469
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile