The Gap Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

The Gap 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 NT$4,214 per night from May 26 to May 27
NT$4,214
NT$5,010 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,137 reviews)
"No Valet parking. Could not come and go from offsite parking without repaying $67.00 Very short on staff."

Reviewed on 2026/5/24

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$5,511 per night from May 27 to May 28
NT$5,511
NT$7,452 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,236 reviews)
"Best hotel breakfast buffet I’ve ever experienced, so many options."

Reviewed on 2026/5/25

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is NT$5,037 per night from May 27 to May 28
NT$5,037
NT$5,989 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 2026/5/24

The Chicago Hotel Collection - Magnificent Mile
See all 4,607 properties in The Gap
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.

Discover the most popular places to visit in The Gap

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

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