Southwest Wisconsin All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
Photo by Inbal Arieh
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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 Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥238,023, price is now ￥192,498 per person
￥192,498
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was ￥235,598, price is now ￥198,214 per person
￥198,214
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥301,802, price is now ￥255,608 per person
￥255,608
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
The Emily Hotel
Downtown Chicago
Price was ￥241,574, price is now ￥208,057 per person
￥208,057
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southwest Wisconsin
View all trips5* All inclusive vacations in Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥301,802, price is now ￥255,608 per person
￥255,608
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥271,656, price is now ￥261,632 per person
￥261,632
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Room was great and staff very attebtive and kind
Reviewed on Jan 20, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southwest Wisconsin
View all trips3 Night All inclusive vacations in Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥238,023, price is now ￥192,498 per person
￥192,498
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was ￥235,598, price is now ￥198,214 per person
￥198,214
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southwest Wisconsin
View all trips4 Night All inclusive vacations in Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,054, price is now ￥389,742 per person
￥389,742
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥543,549, price is now ￥431,088 per person
￥431,088
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥510,170, price is now ￥440,616 per person
￥440,616
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Friendly staff, accommodating- we arrived earlier than our check-in time and they were able to get us in our room promptly.
Reviewed on Feb 3, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southwest 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.
