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
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $273, price is now $169 per person
$169
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Room was wonderful and clean!
Reviewed on Dec 6, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $401, price is now $242 per person
$242
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $699, price is now $434 per person
$434
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $715, price is now $450 per person
$450
per person
Jan 27 - Feb 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone!
Reviewed on Nov 20, 2025
La Banque Hotel
Save 100% on your flight
Price was $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
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
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.
The Gap Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Dec 18 to Dec 19
$111 total
Dec 18 - Dec 19
Total with taxes and fees
8.4/10 Very Good! (5,351 reviews)
Great location, beautiful property, excellent breakfast, spacious rooms.
Reviewed on Dec 3, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $123 total per night from Dec 14 to Dec 15
$123 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (3,433 reviews)
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
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 28 to Dec 29
$145 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (2,115 reviews)
great stay
Reviewed on Dec 5, 2025
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.
Discover the most popular places to visit in The Gap
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
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
4.5/5(4,870 reviews)
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
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.