The Loop Vacations from $202
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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.
Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $312, price is now $202 per person
$202
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,555 reviews)
Everything was AWESOME!!!
Reviewed on Jan 19, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,572, price is now $892 per person
$892
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $450, price is now $264 per person
$264
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room. Extremely friendly staff and beautiful atmosphere.
Reviewed on Jan 20, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,160, price is now $726 per person
$726
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast
Reviewed on Jan 4, 2026
The Royal Sonesta Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $345, price is now $220 per person
$220
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,062 reviews)
The room was fine. The menu for the connected restaurant, Hoyts was super underwhelming. If you look online at their menu, it is extensive and looks pretty good but once we got down to the restaurant, it was about a quarter of the offerings. We did not eat there. I booked a room with a city view and that is not the room that I got. The room overlooked a couple of industrial roofs with AC and heating units and other things like that and the backs of a couple ugly buildings. We absolutely did not have a city view by any stretch of the imagination which was super disappointing. When I booked my reservation confirmation said that I had a $10 food or beverage room credit that I was never given. I booked this room because it was my daughter‘s birthday and she wanted to be in the city and able to look out our room window and view the city so this was extremely disappointing for us.
Reviewed on Jan 17, 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
$87 nightly
The price is $102 total per night from Jan 24 to Jan 25
$102 total
Jan 24 - Jan 25
Total with taxes and fees
8/10 Very Good! (9,797 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...
Reviewed on Jan 20, 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 Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (2,553 reviews)
Did not have breakfast
Reviewed on Jan 19, 2026
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $185 total per night from Feb 15 to Feb 16
$185 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (3,262 reviews)
Clean room, excellent staff
Reviewed on Jan 19, 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
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Chicago Riverwalk
4.5/5(1,535 reviews)
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.
Willis Tower
4.5/5(3,369 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Things to do
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Chicago Blackhawks Ice Hockey Game at United Center
$67
per adult
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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.