The Gap Holidays from AU$1,953

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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

Sheraton Suites Chicago Elk Grove

3.5 out of 5
Price was AU$2,924, price is now AU$1,953 per person
AU$1,953
per person
1 Feb - 8 Feb
found 2 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
16/10 Exceptional! (1,002 reviews)
There was only one elevator working, but they had the service elevator working as well. There was still a long wait for an elevator at times. There was no cooling system available in the room was hot, so we left the windows open. When we got there, there was pubic hair in the bathtub and a used wash cloth laying underneath the shower curtain on the tub side other than that or stay was pleasant

Reviewed on 18 Nov 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was AU$3,042, price is now AU$2,012 per person
AU$2,012
per person
1 Feb - 8 Feb
found 2 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
17.2/10 Exceptional! (2,617 reviews)
The rooms were ok. There is little counter space and it looks and feels a little old and needs a refresh.

Reviewed on 21 Nov 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was AU$3,043, price is now AU$2,014 per person
AU$2,014
per person
1 Feb - 8 Feb
found 2 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
14.4/10 Exceptional! (1,003 reviews)
The room was clean but the air flow was terrible. Very stuffy and felt like the dust particles was in the room. Maybe the air filters should be change.

Reviewed on 17 Nov 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was AU$2,991, price is now AU$1,981 per person
AU$1,981
per person
1 Feb - 8 Feb
found 2 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
18/10 Exceptional! (2,591 reviews)
The staff were amazing! Went above and beyond expectations. Our room was so fun watching planes land and take off! Hotel was very clean and beds very comfortable! We will be staying again.

Reviewed on 19 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$4,074, price is now AU$2,711 per person
AU$2,711
per person
1 Feb - 8 Feb
found 2 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
16.4/10 Exceptional! (2,158 reviews)
Rooms are a little dated, but clean and comfortable. Location across from the airport is quite convenient. Carry out café was good. Sit down restaurant had very tasty dinners and huge portions. Staff was consistentlyknowledgeable, polite, and cheerful.

Reviewed on 20 Nov 2025

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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

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.

Find hotels in Downtown Chicago

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
See all 4,622 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.
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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

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
United Center

United Center

5/5(8 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

United Center

Activities

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$68
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$38
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.