Central Chicago All inclusive Vacations
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Top All inclusive vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥478,828, price is now ￥397,772 per person
￥397,772
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥396,582, price is now ￥343,612 per person
￥343,612
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥478,828, price is now ￥397,772 per person
￥397,772
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips3 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 ￥316,616, price is now ￥269,518 per person
￥269,518
per person
Mar 11 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥360,070, price is now ￥301,847 per person
￥301,847
per person
Mar 11 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 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 ￥396,582, price is now ￥343,612 per person
￥343,612
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥478,828, price is now ￥397,772 per person
￥397,772
per person
Mar 7 - Mar 11
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
