The Loop Vacations from $617
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $984, price is now $617 per person
$617
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,310, price is now $715 per person
$715
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Comfy beds, great staff, great shower, great breakfast
Reviewed on Mar 13, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,083, price is now $665 per person
$665
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,168, price is now $747 per person
$747
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.
Reviewed on Mar 14, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,258, price is now $838 per person
$838
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Great location, clean and very nice restaurant and bar.
Reviewed on Mar 9, 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
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,927 reviews)
Cool historical hotel
Reviewed on Mar 14, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $182 total per night from Apr 1 to Apr 2
$182 total
Apr 1 - Apr 2
Total with taxes and fees
8.6/10 Excellent! (2,675 reviews)
The location was great we walked to the Shedd aquarium in no time. The hotel was nice, we found it really irritating that we were constantly asked to join Hilton rewards by the staff standing at the elevators. Also you can not control the room temperature it was so hot and their solution was to open ...
Reviewed on Mar 13, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $215 total per night from Apr 5 to Apr 6
$215 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (3,473 reviews)
Very good
Reviewed on Mar 13, 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.
Discover the most popular places to visit in The Loop
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Chicago Riverwalk
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
Chicago Theatre
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
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- Chicago Vacations
- Visit Downtown Chicago
- Visit Chicago
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- 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.