
The Gap Vacations from $169
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Your The Gap Vacation
Our The Gap vacation packages are an easy and handy way to arrange and book your next break. Experience the magic of this unique neighborhood without the hassle of organizing 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 Center. Stop dreaming and start doing. When you're ready to book your next vacation to The Gap, Expedia will help get you there.
The Latest The Gap Vacation Packages

Fairmont Chicago at Millennium Park
Reviewed on Dec 6, 2025

The Emily Hotel
Reviewed on Nov 26, 2025

Trump International Hotel & Tower Chicago
Reviewed on Dec 2, 2025

Chicago Athletic Association, a Hyatt Hotel
Reviewed on Nov 20, 2025

La Banque Hotel
Reviewed on Nov 30, 2025
Where to stay in The Gap

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Gap Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
Great location, beautiful property, excellent breakfast, spacious rooms.
Reviewed on Dec 3, 2025

Hilton Chicago/Magnificent Mile Suites
Great Experience and Greater Trip. Chicago was a vibe. Full of fun happiness and joyful memories.
Reviewed on Dec 6, 2025

Palmer House a Hilton Hotel
great stay
Reviewed on Dec 5, 2025
Discover the most popular places to visit in The Gap

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Chicago Bulls Basketball Game at United Center
























