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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

Downtown Chicago
¥338,580
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,119 reviews)
We felt welcome and safe. Everything went smoothly and easy to stay.

Reviewed on Sep 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥394,474
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥354,634
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥434,350
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,018 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥343,314
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.8/10 Excellent! (2,341 reviews)
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5* All inclusive vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥394,474
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥434,350
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,018 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥497,991
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
I liked everything about this

Reviewed on Sep 6, 2026

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3 Night All inclusive vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥271,980
per person
Nov 30 - Dec 3
found 23 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
The views from the hotel were breathtakingly beautiful. The food, the shops, restaurants, entertainment, etc. on the premises were Top Tier. I highly recommend this stay!

Reviewed on Sep 6, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥277,992
per person
Nov 30 - Dec 3
found 23 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥298,450
per person
Nov 30 - Dec 3
found 23 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,839 reviews)
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4 Night All inclusive vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago
¥383,792
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
9/10 Wonderful! (2,824 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥387,412
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip flight included
Hiroshima (HIJ) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
The views from the hotel were breathtakingly beautiful. The food, the shops, restaurants, entertainment, etc. on the premises were Top Tier. I highly recommend this stay!

Reviewed on Sep 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥399,682
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The Riu Plaza is more of a 2-3 star hotel staying there this week. Here are the reasons I experienced. Bed linen and towels dirty for 2 days having to be changed by cleaning staff. One bathroom sink stopped up. We visited the restaurant on the roof which had a nice ambiance but the service was extremely slow with the spicy wings I ate that did not agree with my stomach. Unfortunately there is no business center on the premises. The self-parking garage the hotel recommended is very scary. Overall, we were highly disappointed with the 3 night stay at the Riu Plaza and do not recommend it.

Reviewed on Sep 6, 2026

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.