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The Latest The Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
I loved our stay. The view was unbelievable. The tub was the only concern, it was leaking the water out from the drain area so i had to use more water. That was not a tragedy but just so you guys know it could use a small fix.
Reviewed on May 22, 2024
Park Hyatt Chicago
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!
Reviewed on May 19, 2024
Level Chicago – Old Town
Downtown Chicago
per person
Aug 12 - Aug 15
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.
Reviewed on Mar 16, 2024
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
4 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 ¥23,296 per night from May 27 to May 28
¥23,296
per night
May 27 - May 28
7.6/10 Good! (6,787 reviews)
Historic hotel
"I enjoyed staying at the historical hotel but definitely the room could use a refresher."
Reviewed on May 22, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥25,166 per night from May 27 to May 28
¥25,166
per night
May 27 - May 28
8.6/10 Excellent! (2,879 reviews)
"Absolutely loved our one night stay here! The building is beautiful, the room was so clean and modern, the view of the river was spectacular and the check in/out process was as easy and fast as can be! Super close to all restaurants, bars, and stores. Definitely will be staying here again!"
Reviewed on May 21, 2024
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥23,677 per night from May 27 to May 28
¥23,677
per night
May 27 - May 28
8.4/10 Very Good! (3,048 reviews)
"Good location to downtown. Comfortable bed! I enjoyed eating at the Elephant and Castle."
Reviewed on May 20, 2024
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 Pizza Tour
¥11,048
Per adult
100% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
¥6,916
Per adult
98% of travellers recommend
Chicago C3® by CityPASS®
¥15,026
Per adult
78% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.