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.

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jul 24 - Jul 31

    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG + Flight

    Des Plaines
    7 nights
    3.0 star property
    8.8/10 - Excellent (1,851 reviews)
    "Nice hotel with solid amenities and reasonable nightly rates. Our flight got delayed and then canceled, so we ended up staying in Chicago overnight. This hotel was just what we needed to get a few hours of rest. We’re big fans of Holiday Inn Express! They always deliver and you can count on them being reliable."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$3,571
    AU$3,041
    per traveller
    found 1 hour ago
    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
  • Bar (on property)
    Jul 24 - Jul 31

    Embassy Suites by Hilton Chicago O'Hare Rosemont + Flight

    Rosemont
    7 nights
    4.0 star property
    8.8/10 - Excellent (1,385 reviews)
    "Stayed at Embassy Suites by Hilton Chicago O’Hare Rosemont during our Chicago family trip. Overall, the stay was decent and I would rate it around 7/10. The main advantages were free parking, complimentary breakfast, and convenient access to downtown Chicago, which was roughly a 30-minute drive. The breakfast was good, though vegetarian options were somewhat limited. The room size with the 2 Queen Suites setup was comfortable for family travel. However, the interior ambience was not..."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,417
    AU$3,563
    per traveller
    found 1 hour ago
    Embassy Suites by Hilton Chicago O'Hare Rosemont
  • Bar (on property)
    Jul 24 - Jul 31

    DoubleTree by Hilton Chicago - North Shore Conference Center + Flight

    Skokie
    7 nights
    4.0 star property
    8.8/10 - Excellent (1,010 reviews)
    "Bathtub and bedding were not clean. Tub had a black ring. Water was standing to the ankle during shower. Maintenance came 3x before shower was unclogged, My daughter pulled out hair from drain. There was black stuff in tub and wall after maintenance came for the 4th time. Hotel was booked could not move to another room."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$3,719
    AU$3,151
    per traveller
    found 1 hour ago
    DoubleTree by Hilton Chicago - North Shore Conference Center
  • Terrace/patio
    Jun 24 - Jun 28

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,878 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,435
    AU$4,637
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Seasonal outdoor pool, pool loungers
    Jun 24 - Jun 28

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,231 reviews)
    "We had an incredible stay here. The room was very nice as we stayed in a junior suite so the extra charge was definitely worth it. You’re on the 17th floor and you’re able to have a good view of the city. You also are one floor away from the rooftop restaurant and bar. The decor and aesthetics in the hotel are top-notch. Definitely picture worthy. Definitely walkable and it’s less than quarter mile from the hotel to the lake. 10 out of 10 definitely recommend."
    Reviewed May 23, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,114
    AU$4,381
    per traveller
    found 1 day ago
    Viceroy Chicago

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

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$223 per night from 25 May to 26 May
AU$223
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,135 reviews)
"No Valet parking. Could not come and go from offsite parking without repaying $67.00 Very short on staff."

Reviewed on 24 May 2026

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 AU$387 per night from 26 May to 27 May
AU$387
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (4,226 reviews)
"Could not have asked for a better hotel! Close to everything, excellent staff, beautiful property"

Reviewed on 24 May 2026

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 AU$203 per night from 26 May to 27 May
AU$203
26 May - 27 May
includes taxes & fees
7.8/10 Good! (1,466 reviews)
"Excellent location within walking distance of bars , restaurants and transit. Clean and spacious rooms."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,613 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
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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

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

Naval Base Great Lakes

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(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

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

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
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$34
per adult
88% 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.