
The Loop Vacations from $323
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


Arlo Chicago
Reviewed on Jun 29, 2025

Hotel Riu Plaza Chicago
Reviewed on Jun 30, 2025

Warwick Allerton - Chicago
Reviewed on Jun 30, 2025
Where to stay in The Loop

Downtown Chicago
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

Reviewed on Jun 29, 2025

Reviewed on Jun 29, 2025

Reviewed on Jun 28, 2025
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

Chicago: Architecture Boat Tour with Drinks

Chicago: Navy Pier Centennial Wheel Ticket
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Daley Plaza
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- Marshall Field Building
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- Goodman Theater
- Miró's Chicago
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