The Loop Vacations from $458
Book a Hotel + Flight or Car together to unlock savings
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 $939, price is now $512 per person
$512
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
It waa right downtown, very clean smell great, staff awesome, but parking sucks, paying 55 dollars foe 24 h p irs and no in and out was hard. We had a car but jad ro ulber due to parking. And no pool
Reviewed on Sep 10, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $964, price is now $607 per person
$607
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on Sep 8, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $867, price is now $563 per person
$563
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
$179 nightly
The price is $210 total per night from Sep 22 to Sep 23
$210 total
Sep 22 - Sep 23
Total with taxes and fees
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $209 total per night from Sep 14 to Sep 15
$209 total
Sep 14 - Sep 15
Total with taxes and fees
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $346 total per night from Sep 21 to Sep 22
$346 total
Sep 21 - Sep 22
Total with taxes and fees
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
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
$42
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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.