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

Galewood Vacations from $313

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The Latest Galewood Vacation Packages

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  • A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.
    Jan 14 - Jan 17

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (2,387 reviews)
    "Fantastic budget friendly hotel just steps from the Magnificent Mile! We couldn’t have asked for a better location and our two rooms were comfortable for 2 adults and 3 teenagers. As others have said, the elevators are small (max five people) and there are only 2 for 16 floors. However, it was never a long wait. Rooms weren’t fancy but were clean and comfortable. We had no complaints!"
    Reviewed November 9, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $460
    $313
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Dec 31 - Jan 3

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,668 reviews)
    "Great location to Miracle Mile, restaurants and grocery store!"
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop MDW - ATL • Nonstop
    $888
    $608
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A rooftop lounge with outdoor seating and a city skyline view.
    Jan 28 - Jan 31

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop MDW - ATL • Nonstop
    $704
    $483
    per traveler
    found 3 hours ago
    Pendry Chicago
  • An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
    Dec 10 - Dec 13

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

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,775 reviews)
    "The property was amazing and my view from the 7th floor high corner was immaculate! I will be coming back in warmer weather days"
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $632
    $442
    per traveler
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • A room with two chairs and a small table, a large window with a city view at night.
    Dec 31 - Jan 3

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (3,993 reviews)
    "Good but the condition of the room wasn’t the best."
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop MDW - ATL • Nonstop
    $812
    $573
    per traveler
    found 1 day ago
    Eurostars Magnificent Mile

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
Learn more about Galewood
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Galewood Hotel Deals

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0 star property
7.3 mi from Galewood
9.0 out of 10, Wonderful, (3,221 reviews)
"Amazing service"
$137 nightly
The price is $156
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Chicago O'Hare – Rosemont by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.