The Loop Vacations from $528
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Your The Loop Vacation
Experience the best that The Loop has to offer with a tailor-made The Loop vacation package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighborhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop vacation into reality, no matter your budget or travel plans.
The Latest The Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $799, price is now $528 per person
$528
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,935 reviews)
The staff at the front desk was fabulous and the the room was clean
Reviewed on Jun 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,361, price is now $745 per person
$745
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
My parents stayed here while in town visiting. They had a fantastic experience, appreciating how clean the rooms were and the excellent variety at breakfast. The only hiccup was an exterior bell hop refusing to let my 72 year old father use the luggage trolley himself. Of course he was happy to provide use of the trolley for a tip…
Reviewed on Jun 17, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,121, price is now $719 per person
$719
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.
Reviewed on Jun 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,229, price is now $809 per person
$809
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $761 per person
$761
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
Where to stay in The Loop
Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop
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 Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,293 reviews)
"Good stay and requested a quiet room. AC is very cold but I like it cold in Chicago summer. Shower lukewarm first day and a bit cold side in second day."
Reviewed on Jun 17, 2026
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $277 total per night from Jul 7 to Jul 8
$277 total
Jul 7 - Jul 8
Total with taxes and fees
8.8/10 Excellent! (2,201 reviews)
"We stayed at the Fairmont in the King Gold Suite for my daughter’s college graduation ceremony weekend. The room was spacious to accommodate 3 adults. Excellent amenities, location, and service."
Reviewed on Jun 17, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $148 total per night from Jul 5 to Jul 6
$148 total
Jul 5 - Jul 6
Total with taxes and fees
7.6/10 Good! (2,595 reviews)
"The rooms could have been more up-to-date"
Reviewed on Jun 16, 2026
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.
Stay near popular The Loop attractions
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- Chicago Vacations
- Visit Downtown Chicago
- Visit Chicago
- Where to stay in Chicago
- Daley Plaza
- Chicago Theatre
- Picasso Statue
- Chase Tower
- Willis Tower
- Marshall Field Building
- Richard J. Daley Center
- Noble Fool Theater
- Goodman Theater
- Miró's Chicago
- Chicago Riverwalk
- Chicago Temple
- State Street
- Chicago Cultural Center
- Sullivan Center
- Chicago City Hall
- Navy Pier
- Millennium Park
- Chicago Loop Synagogue
- Chagall's Four Seasons
- Cibc Theatre
- Cadillac Palace Theatre
- Art Institute of Chicago
- Haskell Building
- Cloud Gate
- Marina City
- Carbide and Carbon Building
- Marquette Building
- House of Blues Chicago
- Aon Center
- Crown Fountain
- Rookery
- Chicago Board of Trade Building
- Harris Theater
- Harold Washington Library Center
- Museum of Broadcast Communications
- Monadnock Building
- Depaul University-Loop Campus
- 333 West Wacker Drive
- Symphony Center
- Chicago Symphony Orchestra
- Skydeck Ledge
- Michigan Avenue Bridge
- Civic Opera House
- Fisher Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.