Galewood Vacations from $482
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The Latest Galewood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $841, price is now $482 per person
$482
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on Aug 25, 2025
The Emily Hotel
Downtown Chicago
Price was $1,391, price is now $704 per person
$704
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,040, price is now $550 per person
$550
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,110, price is now $1,141 per person
$1,141
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on Aug 25, 2025
Where to stay in Galewood
Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
Downtown Chicago
5 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.
Galewood Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 2 to Sep 3
$177 total
Sep 2 - Sep 3
Total with taxes and fees
8.2/10 Very Good! (1,220 reviews)
Room clean and modern
"It was great and I appreciated the friendly staff and the cleanliness of my room. It was also very modern and just felt up to date."
Reviewed on Aug 25, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."
Reviewed on Aug 25, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $188 total per night from Sep 4 to Sep 5
$188 total
Sep 4 - Sep 5
Total with taxes and fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."
Reviewed on Aug 27, 2025
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.
Discover the most popular places to visit in Galewood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.