Galewood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Galewood
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $1,303
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Our shower head continually sprayed the bathroom floor. The shower curtain needed to be longer.
Reviewed on Aug 22, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,851
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $2,174
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago
Reviewed on Aug 22, 2026
Where to stay in Galewood
Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
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.
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.
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.
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.
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
CA $141
CA $167 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,288 reviews)
"Convenient to many attractions. Comfortable room. Fastest elevators! Favorite place to stay in Chicago!"
Reviewed on Aug 23, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
CA $234 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $345
CA $405 total
Sep 12 - Sep 13
includes taxes & fees
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.
Frequently asked questions
How much does a Galewood vacation package cost?
From just CA $1,303. 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.