The Gap Holidays

Book a Hotel + Flight or Car together to unlock savings

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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in The Gap

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.287.701 ₫ per night from 25 May to 26 May
2.287.701 ₫
3.524.392 ₫ total
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,670 reviews)
loved my stay!

Reviewed on 3 May 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is 3.562.013 ₫ per night from 26 May to 27 May
3.562.013 ₫
4.235.126 ₫ total
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,159 reviews)
Staff was very friendly!

Reviewed on 3 May 2026

River Hotel
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 3.301.986 ₫ per night from 8 May to 9 May
3.301.986 ₫
3.925.963 ₫ total
8 May - 9 May
includes taxes & fees
8/10 Very Good! (10,145 reviews)
3rd time there. Very clean and close to everything

Reviewed on 4 May 2026

Congress Plaza Hotel
See all 4,616 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 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 1null000null000 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.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

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

Naval Base Great Lakes

5/5(1 review)

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
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

McCormick Place