Chicago Vacations from ￥251,298
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Chicago luxury home suites
Downtown Chicago
Price was ￥577,256, price is now ￥439,498 per person
￥439,498
per person
Feb 19 - Feb 23
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥379,200, price is now ￥302,369 per person
￥302,369
per person
Feb 21 - Feb 25
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on Dec 1, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥320,168, price is now ￥261,760 per person
￥261,760
per person
Feb 19 - Feb 23
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall
Reviewed on Dec 1, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥419,270, price is now ￥343,284 per person
￥343,284
per person
Feb 19 - Feb 23
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Excellent service throughout the hotel
Reviewed on Nov 29, 2025
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,669 per night from Dec 18 to Dec 19
￥14,669
￥17,220 total
Dec 18 - Dec 19
includes taxes & fees
8.4/10 Very Good! (5,350 reviews)
It was great
Reviewed on Dec 1, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,958 per night from Dec 7 to Dec 8
￥12,958
￥15,211 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,429 reviews)
3 day business trip. Hotel is a great location to dow,town. Easy walk to great restaurants and stores
Reviewed on Dec 2, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,521 per night from Dec 28 to Dec 29
￥16,521
￥23,298 total
Dec 28 - Dec 29
includes taxes & fees
8.4/10 Very Good! (2,116 reviews)
Great
Reviewed on Dec 1, 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.
Discover the most popular places to visit in Chicago
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
￥7,083
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,866
per adult
84% of travellers recommend
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