The Gap Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NT$25,000 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
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.
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.
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.
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
NT$3,765
NT$4,476 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very Good! (10,082 reviews)
"Historic hotel that has some upgrades and modern amenities. The lobby bar could use some upgrades and a second working elevator on the South tower would have been helpful on busy days."
Reviewed on 2026/10/22
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NT$3,910
NT$4,649 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very Good! (2,558 reviews)
"Disappointed"
Reviewed on 2026/10/22
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
NT$3,776
NT$4,489 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (5,552 reviews)
"Great location, v helpful staff"
Reviewed on 2026/10/22
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 . 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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.