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



Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥351,899, price is now ¥318,035 per person
¥318,035
per person
Dec 27 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Front desk very helpful with a check-in update. Good access to loop transportation.
Reviewed on Oct 14, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥351,929, price is now ¥326,088 per person
¥326,088
per person
Dec 27 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Beautiful hotel! Would stay again
Reviewed on Oct 14, 2025

Kinzie Hotel
Downtown Chicago
Price was ¥322,752, price is now ¥299,498 per person
¥299,498
per person
Dec 27 - Jan 2
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,903 reviews)
The staff was incredible. They were very friendly, helpful, and attentive to our needs. The hotel was very clean and high quality. Will stay there again!
Reviewed on Oct 11, 2025
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View all trips3 Night All inclusive vacations in Southwest Wisconsin
Price found within the past 48 hours. Click for updated prices.

Graduate by Hilton Madison
Downtown Madison
Price was ¥255,076, price is now ¥245,876 per person
¥245,876
per person
Dec 9 - Dec 12
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Madison (MSN)
9/10 Wonderful! (1,002 reviews)
We have come to prefer staying at Graduate hotels in any town that has them, even if we have no business with the Universities they are associated with. The hotels are always clean, comfortable, and staffed by friendly students. Front desk staff went out of their way to recommend great places to eat as well as printing out something for me that I needed. Truly outstanding service.
The decor is locally themed and unusual. Most places have a great coffee counter (Poindexters) to get your morning Joe and this one even had a rooftop bar. They are in the heart of a college campus, so not necessarily quiet, but the vibe is always lively and since it is in proximity to college kids, there are always a bunch of great and inexpensive dining options. This location in particular had an amazing array of things to do and places to get a great brat and some curds (Memorial Student Center is aces with views of the lake. Go to Der Rathskeller). The proximity to Lake Mendota and the Lakeshore Nature Preserve is fabulous. My only complaint is that the valet parking (pretty much the only available option) is a gouge, but the staff was lovely and you can get your car in and out as many times a day as you need. I would absolutely stay here again.
Reviewed on Oct 3, 2025

Hilton Madison Monona Terrace
Downtown Madison
Price was ¥267,654, price is now ¥251,916 per person
¥251,916
per person
Dec 9 - Dec 12
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to Madison (MSN)
8.6/10 Excellent! (1,002 reviews)
Beautiful hotel, right on the lake and downtown Madison, near great restaurants!
Reviewed on Oct 12, 2025

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