The Loop Vacations from $203
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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.
Hyatt Place Chicago/ Schaumburg
Save 100% on your flight
Price was $360, price is now $203 per person
$203
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
Everything was wonderful except those small square pillows, not sure who's idea that was
Reviewed on Dec 17, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $723, price is now $411 per person
$411
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,242, price is now $707 per person
$707
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
From staff to room it was a amazing experience.
Reviewed on Dec 18, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $430 per person
$430
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $546, price is now $322 per person
$322
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on Dec 8, 2025
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
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,136 reviews)
Clean room, amazing bathroom. Very wonderful stay. Parked in Palmer house parking garage and walked to hotel. Close to many nice restaurants and in the heart of downtown.
Reviewed on Dec 19, 2025
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 Dec 25 to Dec 26
$103 total
Dec 25 - Dec 26
Total with taxes and fees
8.6/10 Excellent! (1,992 reviews)
Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning.
Reviewed on Dec 16, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Dec 26 to Dec 27
$174 total
Dec 26 - Dec 27
Total with taxes and fees
8.4/10 Very Good! (2,142 reviews)
Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive.
Reviewed on Dec 19, 2025
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
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Willis Tower
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
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
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.