Galewood Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Galewood

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

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Good price, good service.

Reviewed on May 29, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
What a wonderful day

Reviewed on May 29, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 27 - Jul. 31
found 11 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (655 reviews)
Very clean and modern 10/10

Reviewed on May 28, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 7 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Loved all the neighborhood dogs & farmers market

Reviewed on May 20, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 7 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Parking around the hotel is horrible, so they are able to charge an arm and a leg for valet! If you come & go often, then the price is worth is as there is a paid parking lot just a short walk to the corner from the hotel. Also the restaurant was FREEZING,

Reviewed on May 28, 2024

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
Downtown Chicago showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Galewood Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Jun. 5 to Jun. 6
CA $255
CA $300 total
includes taxes & fees
Jun 5 - Jun 6
7.6/10 Good! (6,816 reviews)
"Be aware there is only Analog TV in the room"

Reviewed on May 29, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is CA $216 per night from Jul. 1 to Jul. 2
CA $216
CA $254 total
includes taxes & fees
Jul 1 - Jul 2
8.6/10 Excellent! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on May 28, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jun. 30 to Jul. 1
CA $233
CA $273 total
includes taxes & fees
Jun 30 - Jul 1
8.2/10 Very Good! (1,901 reviews)
"Thank you everything was great"

Reviewed on May 29, 2024

Eurostars Magnificent Mile
See all 4,484 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Galewood vacation package cost?
From just CA $1,008. Yes, you read that right. Our Galewood packages are a simple way to make your dollars go much further. Combine your favorite hotels, flights and rental car and get out and explore this wonderful destination.
How do I get a cheap travel package to Galewood?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Galewood vacation package to save loads of cash. Score even better deals when you add extras such as activities or tours to your booking. But that’s not the only impressive part. You have the freedom to put together your vacation your own way. We offer more than 550 airlines and 1,000,000 properties throughout the world, so that everyone has an opportunity to travel and live out those vacation fantasies.
Where should I stay in Galewood?
Most who travel to Galewood include University of Illinois Chicago and United Center on their sightseeing itineraries. Why not reserve a hotel as close as possible to these main attractions?
How far in advance should I book my Galewood vacation?
It’s always wise to book early. Air carriers usually advertise flight tickets around a year ahead of departure, and this is when you can land some rock-bottom prices. Just been told you should take some vacation time next week? That’s alright! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Galewood travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Galewood package that’s ideal for you. Vacationing for a week or longer? Consider a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal may be more your style. Activities can also be added after you’ve booked. Our travel packages make it a breeze to save and plan.
What should I know before booking a Galewood travel package?
Our prices are already low. However, you’ll snap up even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with a Galewood Expedia vacation package?
Yes — that’s one of the best things about an Expedia vacation package. You get to choose. We have more than 550 airline partners across the globe, so you have loads of choice when putting together your Galewood adventure.
If I'm not able to travel, can I cancel my Galewood vacation package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Galewood vacation package for free if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Looking for more information? Check out our Customer Service Portal. We’ll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Galewood

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.