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The Latest Downtown Chicago Vacation Packages
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Jun 4 - Jun 10
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,132 reviews)
A beautiful Hotel. Very clean & spa like. Wonderful pool/gym/locker room area. Staff very nice. Food was excellent.
Reviewed on Mar 29, 2024
Level Chicago – Old Town
Downtown Chicago
per person
Jun 4 - Jun 10
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (204 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
Prices and availability subject to change. Additional terms may apply.
Where to stay in Downtown Chicago
Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
Downtown Chicago Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥14,241 per night from Mar 31 to Apr 1
¥14,241
per night
Mar 31 - Apr 1
8.4/10 Very Good! (2,931 reviews)
"Good deal. Small room. Pretty small lobby. Comfortable bed and pillows. Staff was great. Location was amazing. Easy walk to any of the downtown theaters. Lots of restaurants close by. Would stay again!"
Reviewed on Mar 28, 2024
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥16,838 per night from Apr 1 to Apr 2
¥16,838
per night
Apr 1 - Apr 2
7.6/10 Good! (6,459 reviews)
"As others have mentioned, this place is daaaaated. It was probably a fancy hotel back in its time but it definitely older now. That being said, it's a great place location wise particularly given the price. The rooms are old but clean. The service is good. The heating is centralized and it was cold ..."
Reviewed on Mar 28, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥15,680 per night from Mar 31 to Apr 1
¥15,680
per night
Mar 31 - Apr 1
8.6/10 Excellent! (2,720 reviews)
"ㆍ"
Reviewed on Mar 28, 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 Downtown Chicago
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Grant Park
4.5/5(3,318 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
¥30,540
Per adult
76% of travellers recommend
Chicago Pizza Tour
¥11,048
Per adult
100% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
¥3,241
Per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.