Galewood Vacation Packages 2026 from $285

The Latest Galewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Save 100% on your flight

$285

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,015 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$462

per person

Jan 7 - Jan 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$885

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$527

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$398

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,274 reviews)

Nice and convenient to Michigan avenue. Staff is so friendly and helpful!

Reviewed on Oct 20, 2026

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

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

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

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 city street with a train passing overhead, cars, pedestrians, and a red brick building.

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 wooden pavilion with a view of a city skyline and a body of water.

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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$107 nightly

$127 total

Nov 11 - Nov 12

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$121 nightly

$143 total

Nov 11 - Nov 12

Total with taxes and fees

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$152 nightly

$181 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (5,559 reviews)

"Very clean hotel, comfy bed & pillows. Water station was a plus. Great view of the river."

Reviewed on Oct 20, 2026

See all 4,960 properties in Galewood

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.