The Loop Vacations from $334
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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $722, price is now $446 per person
$446
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Excellent location, service, view and food!!
Reviewed on Jan 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $620, price is now $385 per person
$385
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (2,510 reviews)
Staff members were friendly and helpful. Great location walking distance and transportation options.
Reviewed on Jan 9, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $192 total per night from Jan 18 to Jan 19
$192 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (2,226 reviews)
This stay was perfection from beginning to end. Totally wonderful experience in every way.
Reviewed on Jan 9, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Jan 30 to Jan 31
$103 total
Jan 30 - Jan 31
Total with taxes and fees
8.6/10 Excellent! (2,048 reviews)
Pedro and front office staff made our stay excellent. Return customer love the location, room quality and value overall. Room size and features make this our first choice in the city
Reviewed on Jan 7, 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.
Willis Tower
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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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.