Central Chicago All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
Photo by Phil Ostroff
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top All inclusive vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥363,203, price is now ￥303,241 per person
￥303,241
per person
Sep 15 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
Decaf coffee was like colored water--not sure if the 'leaded' was any better.
Would like a clock in the room.
The breakfasts were amazing (except forthat coffee).
Otherwise, a really great stay!
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥441,442, price is now ￥379,004 per person
￥379,004
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥421,500, price is now ￥363,458 per person
￥363,458
per person
Sep 15 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips5* All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was ￥375,831, price is now ￥346,797 per person
￥346,797
per person
Sep 15 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
Excellent hotel and location. 1 min away from Michigan avenue
Reviewed on Jun 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥421,500, price is now ￥363,458 per person
￥363,458
per person
Sep 15 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥480,282, price is now ￥426,559 per person
￥426,559
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
My stay was remarkable! Staff was extremely friendly, room clean, in room dining food was delicious!
Reviewed on Jun 21, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥388,336, price is now ￥334,356 per person
￥334,356
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
Decaf coffee was like colored water--not sure if the 'leaded' was any better.
Would like a clock in the room.
The breakfasts were amazing (except forthat coffee).
Otherwise, a really great stay!
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥441,442, price is now ￥379,004 per person
￥379,004
per person
Aug 9 - Aug 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all tripsThings to do
Wendella's 90-min Chicago River Architecture Tour
￥6,478
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
