The Loop Vacations from $587
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $877, price is now $587 per person
$587
per person
Aug 6 - Aug 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
Modern interior design of the lobby and cleanliness of the room.
Reviewed on Jun 14, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,272, price is now $755 per person
$755
per person
Aug 6 - Aug 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Breakfast, staff, near everything
Reviewed on Jun 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,059, price is now $715 per person
$715
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,248, price is now $865 per person
$865
per person
Aug 6 - Aug 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience
Reviewed on Jun 14, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $948, price is now $657 per person
$657
per person
Aug 6 - Aug 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,799 reviews)
Service at the restaurant for brunch was excellent!
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! (10,279 reviews)
"It was an awesome location, clean, and vintage, which I really loved. Walking you will have to go north to everything which is no more than a 20 minute walk. I didn’t use the bar so I can’t rate that. I didn’t like that there wasn’t a pool but overall service was great. I would definitely stay again ..."
Reviewed on Jun 15, 2026
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $291 total per night from Jul 7 to Jul 8
$291 total
Jul 7 - Jul 8
Total with taxes and fees
8.8/10 Excellent! (2,200 reviews)
"My wife was disappointed that the hotel did not provide room slippers or bathrobes. Upon cleaning the room, the bathroom products were not replaced/refilled. The cleaners did not replace the used coffee mugs."
Reviewed on Jun 15, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $158 total per night from Jul 1 to Jul 2
$158 total
Jul 1 - Jul 2
Total with taxes and fees
7.4/10 Good! (2,644 reviews)
"Employees were fantastic. Room was clean and comfortable. Rates were super reasonable due to early booking."
Reviewed on Jun 14, 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
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels with Free Airport Shuttle in Chicago
- Hotels near Chicago Riverwalk
- Hotels with Free Parking in Chicago
- Hotels near Magnificent Mile
- Extended Stay Hotels in Chicago
- Cheap Hotels in Downtown Chicago
- All-Inclusive Resorts in Chicago
- Hotels near Grant Park
- Hotels with Suites in Chicago
- Motels in Chicago
- Hotels near Millennium Park
- Luxury Hotels in Downtown Chicago
- 5 Star Hotels in Chicago
- Hotels near River North
- Hotels near Michigan Avenue
- Marriott Hotels & Resorts in Chicago
- Hotels with a Pool in Chicago
- Hotels with Balconies in Chicago
- Hotels with Hot Tubs in Chicago
- Romantic Hotels in Chicago
- Hotels near Chicago Theatre
- Pet-Friendly Hotels in Chicago
- Hotels with Early Check-in in Chicago
- Hotels with a View in Downtown Chicago
- Hotels near Chicago Union Station
- Hotels with Kitchenettes in Chicago
- Resorts & Hotels with Spas in Chicago
- Hotels with smoking rooms in Chicago
- Adults Only Resorts & in Chicago
- Hotels with an Indoor Pool in Chicago
- Central Chicago Hotels
- Casino Hotels in Chicago
- Hotels with Connecting Rooms in Chicago
- Motel 6 Hotels in Chicago
- Hotels with an Outdoor Pool in Chicago
- Family Hotels in Chicago
- Hotels near House of Blues Chicago
- Hotels near Soldier Field
- Waterpark Hotels in Chicago
- Hotels with Suites in Downtown Chicago
- Hotels on the River in Chicago
- 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.