
The Loop Holidays
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Your The Loop Holiday
Experience the best that The Loop has to offer with a tailor-made The Loop holiday package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighbourhood. 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 holiday into reality, no matter your budget or travel plans.
Our guide on 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.
Our pick of the best The Loop Hotel Deals

Palmer House a Hilton Hotel
Room is gorgeous!!
Reviewed on 27 Dec 2025

Hilton Chicago
Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!
Reviewed on 27 Dec 2025

Club Quarters Hotel Wacker at Michigan, Chicago
Easy check in. Ready to upgrade. I love how central it is and the water stations on each floor. This is our second time to stay here and will do it again!
Reviewed on 23 Dec 2025
Frequently asked questions
Discover the most popular places to visit in The Loop

Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

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.

Willis Tower
The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.
Activities

Wendella's 90-min Chicago River Architecture Tour
















