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.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥262,870
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
First thing you notice when walking in is how wonderful it smells!! The front desk staff were very friendly and helpful. The room was very nice and they even provide toiletries. The only downside is there is no ice machine or an option for snacks later in the evening. If you contact the front desk they will bring ice up to you.

Reviewed on Aug 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥354,762
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥299,425
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥273,598
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Absolutely, better than amazing view of the Chicago view and lake. Rented the room for a special occasion that worked out great. After searching for other hotels in the area with a great view, this choice was the best choice I could have made. Since Navy Pier is one of Chicago biggest tourist attractions, I highly recommend a comfortable pair of walking shoes. I do think some of the furniture pieces should be updated to something more modern or stylish for the price of the room. It will make the vibe much better. That's my personal opinion. Service was amazing and staff was friendly and very helpful. Parking was very reasonable.

Reviewed on Aug 28, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥274,777
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,314 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
¥354,762
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

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4 Night All inclusive vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥276,589
per person
Nov 2 - Nov 6
found 9 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥292,324
per person
Nov 2 - Nov 6
found 9 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The staff were helpful, the room was nice and clean, and the buffet breakfast was amazing. We enjoyed our stay.

Reviewed on Aug 28, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥304,695
per person
Nov 2 - Nov 6
found 9 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)
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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.