The Gap Holidays

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Your The Gap Holiday

Our The Gap holiday packages are an easy and handy way to arrange and book your next break. Experience the magic of this unique neighbourhood without the hassle of organising everything yourself. Can't wait to explore the sights during your trip to The Gap? Make sure you check out nearby attractions like Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Centre. Stop dreaming and start doing. When you're ready to book your next holiday to The Gap, Expedia will help get you there.

Our guide on 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 featuring a city

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

Our pick of the best 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 AU$227 per night from 2 Nov to 3 Nov
AU$227
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (9,333 reviews)
"Very clean"

Reviewed on 7 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$223 per night from 23 Oct to 24 Oct
AU$223
23 Oct - 24 Oct
includes taxes & fees
7.8/10 Good! (2,425 reviews)
"Excellent location, clean and good room partners"

Reviewed on 6 Oct 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$293 per night from 9 Nov to 10 Nov
AU$293
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"

Reviewed on 7 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,476 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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 homes 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.

Discover the most popular places to visit in The Gap

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.