The Loop Vacations from $278
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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 Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $477, price is now $278 per person
$278
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $625, price is now $368 per person
$368
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $475, price is now $284 per person
$284
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating
Reviewed on Jan 17, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $604, price is now $364 per person
$364
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.
Reviewed on Jan 20, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $654, price is now $395 per person
$395
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on Jan 10, 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
$89 nightly
The price is $104 total per night from Jan 24 to Jan 25
$104 total
Jan 24 - Jan 25
Total with taxes and fees
8/10 Very Good! (9,799 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! (2,555 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
$156 nightly
The price is $183 total per night from Feb 21 to Feb 22
$183 total
Feb 21 - Feb 22
Total with taxes and fees
9.2/10 Wonderful! (3,254 reviews)
The hotel was amazing and really met all our expectations
Reviewed on Jan 21, 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
Explore a world of travel with Expedia
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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.