The Gap Trip
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₹100,000 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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top hotels in The Gap
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₹10,051
₹11,950 total
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
₹13,612
₹16,183 total
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,979 reviews)
"Lobby staff was helpful. Room was not worth the cost - all white furniture with stains on the couch and big moisture stains on the chair in the bedroom. 2 tiny glass cups, crack in bathroom sink, doors hard to latch and got stuck in the frame. Curtains had stains and were pulled off the rod so they ..."
Reviewed on 10 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
₹21,870
₹25,673 total
11 Sept - 12 Sept
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 The Gap holiday package cost?
From just . Yes, you read that right. Our The Gap holiday 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 holiday 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 holiday 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 holiday?
Savvy travellers 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 holiday rentals like oceanfront condos and short-term homes. The list goes on!
Can I choose my airline with a The Gap Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our holiday 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 holiday 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 with a visit to 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.