The Loop Vacations from $208
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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.
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $334, price is now $208 per person
$208
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (2,152 reviews)
Not having coffee available until 6 AM (at an airport!) is just so wrong.
Reviewed on Nov 15, 2025
Sand Hill On The Lake
Save 100% on your flight
Price was $763, price is now $419 per person
$419
per person
Dec 30 - Jan 3
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (77 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl
Reviewed on Nov 10, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was $605, price is now $377 per person
$377
per person
Jan 16 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $149 total per night from Nov 24 to Nov 25
$149 total
Nov 24 - Nov 25
Total with taxes and fees
8.4/10 Very Good! (2,057 reviews)
Excellent!
Reviewed on Nov 13, 2025
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $134 total per night from Nov 19 to Nov 20
$134 total
Nov 19 - Nov 20
Total with taxes and fees
9.2/10 Wonderful! (4,032 reviews)
The real bad thing was there was nowhere to park, leave your car for a few minutes, to check in.
Reviewed on Nov 16, 2025
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 17 to Nov 18
$136 total
Nov 17 - Nov 18
Total with taxes and fees
8/10 Very Good! (9,556 reviews)
Everything about the Congress was lovely. Enjoyed our stay. Perfect location for city adventure.
Reviewed on Nov 14, 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
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.
Art Institute of Chicago
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% 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.