The Gap 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 The Gap
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,427
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
What a wonderful place. This is the second RIU hotel we have stayed at and it was fantastic. Everything from the breakfast to the roof top bar to the comfy beds. I would definitely stay here again.
Reviewed on Aug 31, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,218
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Rooms nice, spacious. Wonderful shower head! excellent city/river view too.
Appreciate the water for $ in the room.
Location nice on the river. It’s close to walk a block or so East to a rooftop bar at Miru (& sushi restaurant yum) in the St.Regis.
The Palm Restaurant downstairs was a great option (Lobster yum).
The hotel is a quick walk down to a rooftop bar at Miru in the St.Regis. And there’s a market to grab things next door in a residential building.
Good hotel, good price. So super quick & easy to grab a taxi or uber to all the quick locations, Navy Pier, Fountain, Park, etc. :)
Reviewed on Aug 31, 2026
Where to stay in The Gap
Find the best The Gap areas and neighborhoods for the activities you enjoy most. Learn more about The Gap
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.
The Gap Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $142
CA $169 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,241 reviews)
"Check-in was super quick and staff was very efficient and helpful. Booked a standard room with a king size bed facing the lake and it was a very nice weekend stay. Room was very clean. The AC is off central heatingThe location is incredibly convenient if you’re going somewhere near the lake or ..."
Reviewed on Aug 31, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $236 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very good! (2,139 reviews)
"Location near the lake and very walkable to train, bus stations, restaurants and stores. Room was not very well cleaned"
Reviewed on Aug 31, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (883 reviews)
"Unfortunately this property was a bad experience. There is little to no communication from the host. Your only option is to talk to a chat bot from California. We tried checking in 10 minutes early and were told that wasn't possible, There was no one at the check-in desk when we got there. The room ..."
Reviewed on Aug 31, 2026
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 The Gap vacation package cost?
From just CA $958. Yes, you read that right. Our The Gap vacation packages are the easiest way to make your budget last longer. Combine your flights, hotels and rental car and explore this popular destination.
How do I get a cheap travel package to The Gap?
Combine your hotels and flights, toss in extras such as a rental car or activities, and save with a The Gap vacation package. You won't just pick up awesome discounts on your escape — you'll have loads of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 properties across the globe. Your affordable vacation begins right here, right now!
Where should I stay in The Gap?
A visit to The Gap has to include University of Chicago and Chicago Museum of Science and Industry. Stay at a hotel right nearby and easily access these terrific attractions.
How far in advance should I book my The Gap vacation?
Savvy travelers often reserve their seats early. You can generally start comparing international airfares on Expedia up to 12 months before your flight. If you're purchasing your ticket at the last minute, fear not. Low prices occasionally become available just weeks before departure.
What does an Expedia The Gap travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to build your perfect The Gap package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Don't forget — the more you bundle, the more deals you'll score!
What should I know before booking a The Gap travel package?
Locking in all the parts of your getaway together is a smart way to save. Bundle your flights, car rentals and hotels into a convenient little package. But you're not limited to hotels. Expedia features all kinds of properties, including vacation rentals like oceanfront condos and short-term homes. The list goes on!
Can I choose my airline with a The Gap Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my The Gap vacation package?
Yes, it's possible to cancel your The Gap booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
Stay near popular The Gap attractions
Robert W Roloson Houses
You can find out about the history of Chicago with a visit to Robert W Roloson Houses. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Captain Ernest A Griffin Place
You can learn about the history of Chicago when you stop by Captain Ernest A Griffin Place. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
Pilgrim Baptist Church
After visiting Pilgrim Baptist Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
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.