Chicago Vacations from ￥258,975
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥312,320, price is now ￥258,975 per person
￥258,975
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥337,890, price is now ￥285,200 per person
￥285,200
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
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.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,356 per night from Jan 22 to Jan 23
￥14,356
￥16,851 total
Jan 22 - Jan 23
includes taxes & fees
8/10 Very Good! (9,799 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...
Reviewed on Jan 20, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,625 per night from Feb 1 to Feb 2
￥20,625
￥28,855 total
Feb 1 - Feb 2
includes taxes & fees
8.4/10 Very Good! (2,555 reviews)
Did not have breakfast
Reviewed on Jan 19, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,733 per night from Feb 9 to Feb 10
￥16,733
￥19,644 total
Feb 9 - Feb 10
includes taxes & fees
8.4/10 Very Good! (5,571 reviews)
Clean rooms, good service, pool area was nice and free breakfast.
Reviewed on Jan 20, 2026
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.
Discover the most popular places to visit in Chicago
Michigan Avenue
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago
Chicago: Navy Pier Centennial Wheel Ticket
￥3,883
per adult
88% of travellers recommend
Chicago Blackhawks Ice Hockey Game at United Center
￥10,515
per adult
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
