
The Loop Vacations
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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
The price is ¥21,871 per night from Sep 23 to Sep 24
¥21,871
¥25,674 total
Sep 23 - Sep 24
includes taxes & fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"
Reviewed on Sep 18, 2025

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥29,426 per night from Sep 28 to Sep 29
¥29,426
¥34,542 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"
Reviewed on Sep 17, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥28,437 per night from Oct 3 to Oct 4
¥28,437
¥38,116 total
Oct 3 - Oct 4
includes taxes & fees
8.8/10 Excellent! (2,028 reviews)
"Staff very friendly."
Reviewed on Sep 16, 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.
Frequently asked questions
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

Chicago By Night River & Lake Cruise
¥6,681
per adult
96% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,646
per adult
84% of travellers recommend

Chicago: Architecture Boat Tour with Drinks
¥6,235
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.