
Southern Wisconsin All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top All inclusive vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
Price was ¥280,959, price is now ¥226,887 per person
¥226,887
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay
Reviewed on Sep 19, 2025


The Emily Hotel
Downtown Chicago
Price was ¥356,734, price is now ¥288,542 per person
¥288,542
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on Sep 26, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥321,722, price is now ¥261,166 per person
¥261,166
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,296, price is now ¥268,442 per person
¥268,442
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.



The Ritz-Carlton, Chicago
Downtown Chicago
Price was ¥279,276, price is now ¥272,536 per person
¥272,536
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one.
Reviewed on Sep 15, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips3 Night All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥366,658, price is now ¥298,221 per person
¥298,221
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥410,157, price is now ¥331,901 per person
¥331,901
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe
Reviewed on Sep 27, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥357,383, price is now ¥302,136 per person
¥302,136
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on Sep 26, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥321,722, price is now ¥261,166 per person
¥261,166
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025


The Emily Hotel
Downtown Chicago
Price was ¥356,734, price is now ¥288,542 per person
¥288,542
per person
Nov 2 - Nov 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on Sep 26, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.