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

Galewood Vacations from $784

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The Latest Galewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Oct 7 - Oct 10

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,642 reviews)
    "Our stay was amazing with a beautiful view."
    Reviewed August 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,266
    $784
    per traveler
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sep 13 - Sep 19

    Level Chicago - River North + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,043 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $3,387
    $1,838
    per traveler
    found 2 days ago
    Level Chicago - River North
  • Front of property
    Sep 13 - Sep 19

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.4/10 - Exceptional (4,929 reviews)
    "I loved the entire staff at the resort and especially the Mahi Mahi restaurant"
    Reviewed August 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $3,177
    $1,774
    per traveler
    found 2 days 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
    Save 100% on your flight
    $4,667
    $2,727
    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
    $2,431
    $1,466
    per traveler
    found 1 day ago
    Level Chicago – Old Town