
Southern Wisconsin All inclusive Vacations
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Top All inclusive vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥338,022, price is now ¥229,282 per person
¥229,282
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though.
Reviewed on Jan 22, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥407,761, price is now ¥319,483 per person
¥319,483
per person
Apr 1 - Apr 6
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026


The Peninsula Chicago
Downtown Chicago
Price was ¥474,268, price is now ¥392,745 per person
¥392,745
per person
Apr 1 - Apr 6
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥275,472, price is now ¥233,604 per person
¥233,604
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
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View all trips5* All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥392,548, price is now ¥280,660 per person
¥280,660
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥474,268, price is now ¥392,745 per person
¥392,745
per person
Apr 1 - Apr 6
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥347,796, price is now ¥328,205 per person
¥328,205
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
Room was great and spacious. Service was great. The pool and sauna were nice also.
Reviewed on Jan 13, 2026
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View all trips4 Night All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hilton Orrington / Evanston
Downtown Evanston
Price was ¥274,210, price is now ¥246,694 per person
¥246,694
per person
Mar 17 - Mar 21
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
I would stay here again if I need to stay in Evanston again. Thanks
Reviewed on Jan 19, 2026


Hilton Chicago O'Hare Airport
O'Hare
Price was ¥328,756, price is now ¥293,110 per person
¥293,110
per person
Mar 17 - Mar 21
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Hotel was very clean. Concierge was great with advice. Sports bar pepperoni pizza was great and the french fries were just as freshly cooked. Room was clean. Bed was great. Shower pressure great. Toilet correct height for a man of my age. Pillows…..pillows with a firmness of that of a 48 year old mother who breast fed all her 7 children until 9 months old. Glad the kids are good but those pillows need work Hilton. God Bless and safe travels to all. See you next time.
Reviewed on Jan 20, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
