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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥339,105, price is now ￥271,120 per person
￥271,120
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It’s a very prime location, absolutely love it.
Reviewed on Mar 13, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!
Reviewed on Mar 13, 2026
Hilton Chicago
Downtown Chicago
Price was ￥605,910, price is now ￥499,852 per person
￥499,852
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on Mar 12, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥419,910, price is now ￥349,994 per person
￥349,994
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥415,929, price is now ￥356,362 per person
￥356,362
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Great room but the beds were really small. The bathroom door was frosted but you could still see through the door and there was a large mirror in front of the bathroom door. To top it off the bathroom door was a sliding door that did not close all the way, so absolutely no privacy in a room that sleeps 4!
Reviewed on Mar 13, 2026
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View all trips5* All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
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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 ￥496,890, price is now ￥358,822 per person
￥358,822
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It’s a very prime location, absolutely love it.
Reviewed on Mar 13, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥465,726, price is now ￥372,726 per person
￥372,726
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026
Level Chicago - River North
Downtown Chicago
Price was ￥452,740, price is now ￥368,338 per person
￥368,338
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (858 reviews)
I would stay here again without a second thought. Great
Reviewed on Mar 11, 2026
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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥505,796, price is now ￥391,960 per person
￥391,960
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great spot and view, would stay again!
Reviewed on Mar 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥574,240, price is now ￥402,408 per person
￥402,408
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It’s a very prime location, absolutely love it.
Reviewed on Mar 13, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥528,000, price is now ￥412,964 per person
￥412,964
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026
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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.
