The Loop Vacations from $357
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 Felix River North/Magnificent Mile
Downtown Chicago
Price was $582, price is now $357 per person
$357
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Clean, wonderful employees they were very kind and accommodating
Reviewed on Feb 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,051, price is now $444 per person
$444
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Location was perfect! Rooms clean and renovated and breakfast was AMAZING! Staff is really nice and friendly. Would love to stay there again.
Reviewed on Feb 23, 2026
La Banque Hotel
Save 100% on your flight
Price was $611, price is now $376 per person
$376
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 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
$93 nightly
The price is $109 total per night from Feb 25 to Feb 26
$109 total
Feb 25 - Feb 26
Total with taxes and fees
8/10 Very Good! (9,926 reviews)
Great place
Reviewed on Feb 22, 2026
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 Mar 5 to Mar 6
$192 total
Mar 5 - Mar 6
Total with taxes and fees
8.4/10 Very Good! (2,650 reviews)
The check in process was smooth. Paul provided excellent customer service. The room had a great view of the lake. Everyone we interacted with was very friendly.
Reviewed on Feb 23, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
$223 nightly
The price is $262 total per night from Mar 24 to Mar 25
$262 total
Mar 24 - Mar 25
Total with taxes and fees
9.2/10 Wonderful! (3,486 reviews)
Yes
Reviewed on Feb 22, 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
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago Bulls Basketball Game at United Center
$166
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels with Free Airport Shuttle in Chicago
- Hotels near Chicago Riverwalk
- Hotels with Free Parking in Chicago
- Hotels near Magnificent Mile
- Extended Stay Hotels in Chicago
- Cheap Hotels in Downtown Chicago
- All-Inclusive Resorts in Chicago
- Hotels near Grant Park
- Hotels with Suites in Chicago
- Motels in Chicago
- Hotels near Millennium Park
- Luxury Hotels in Downtown Chicago
- 5 Star Hotels in Chicago
- Hotels near River North
- Hotels near Michigan Avenue
- Marriott Hotels & Resorts in Chicago
- Hotels with a Pool in Chicago
- Hotels with Balconies in Chicago
- Hotels with Hot Tubs in Chicago
- Romantic Hotels in Chicago
- Hotels near Chicago Theatre
- Pet-Friendly Hotels in Chicago
- Hotels with Early Check-in in Chicago
- Hotels with a View in Downtown Chicago
- Hotels near Chicago Union Station
- Hotels with Kitchenettes in Chicago
- Resorts & Hotels with Spas in Chicago
- Hotels with smoking rooms in Chicago
- Adults Only Resorts & in Chicago
- Hotels with an Indoor Pool in Chicago
- Central Chicago Hotels
- Casino Hotels in Chicago
- Hotels with Connecting Rooms in Chicago
- Motel 6 Hotels in Chicago
- Hotels with an Outdoor Pool in Chicago
- Family Hotels in Chicago
- Hotels near House of Blues Chicago
- Hotels near Soldier Field
- Waterpark Hotels in Chicago
- Hotels with Suites in Downtown Chicago
- Hotels on the River in Chicago
- 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.