The Gap Holidays from AU$1,953

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to AU$703 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

Top Holiday Package Deals in The Gap

Price found within the past 48 hours. Click for updated prices.
Sheraton Suites Chicago Elk Grove
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
DoubleTree by Hilton Chicago Schaumburg
Holiday Inn Chicago O'Hare – Rosemont by IHG
Hilton Chicago O'Hare Airport

Black Friday Sale

Save up to 40% on select hotels

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

Our pick of the best The Gap Hotel Deals

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 23 Dec to 24 Dec
AU$225
23 Dec - 24 Dec
includes taxes & fees
8.4/10 Very Good! (2,073 reviews)
Staff could not have been more helpful. The venue was packed for an international rugby game, but everything was clean, well cared for and comfortable. Will defintiely stay here again!

Reviewed on 18 Nov 2025

Palmer House a Hilton Hotel
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$159 per night from 21 Dec to 22 Dec
AU$159
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt

Reviewed on 18 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 7 Dec to 8 Dec
AU$151
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,335 reviews)
Friendly staff, clean rooms

Reviewed on 19 Nov 2025

Hilton Chicago/Magnificent Mile Suites
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 AU$1,953. 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

Activities

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