
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.


Pendry Chicago
Downtown Chicago
Price was ¥303,328, price is now ¥251,270 per person
¥251,270
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on Sep 8, 2025

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥338,978, price is now ¥282,198 per person
¥282,198
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,912 reviews)
Amazing views and exceptional service
Reviewed on Sep 10, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥291,130, price is now ¥243,804 per person
¥243,804
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025

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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 ¥533,264, price is now ¥326,389 per person
¥326,389
per person
Dec 1 - Dec 3
found 1 day ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on Sep 8, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥569,377, price is now ¥356,444 per person
¥356,444
per person
Dec 1 - Dec 3
found 7 hours ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

Nobu Hotel Chicago
Downtown Chicago
Price was ¥515,066, price is now ¥331,554 per person
¥331,554
per person
Dec 1 - Dec 3
found 7 hours ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.4/10 Exceptional! (718 reviews)
Nobu hotel Chicago is exceptional. Their tasteful design makes me speechless.
Reviewed on Sep 2, 2025
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Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥306,856, price is now ¥238,872 per person
¥238,872
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
It waa right downtown, very clean smell great, staff awesome, but parking sucks, paying 55 dollars foe 24 h p irs and no in and out was hard. We had a car but jad ro ulber due to parking. And no pool
Reviewed on Sep 10, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥409,760, price is now ¥304,676 per person
¥304,676
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on Sep 8, 2025

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