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.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The room was very nice and large. The beds were very comfortable. The views from our room were great.
Reviewed on Aug 21, 2026
Level Chicago - River North
Downtown Chicago
￥342,336
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
I was only there for one night, but the room I stayed in was super clean and had everything I would need - washer/dryer, full kitchen, living space. I did use the office space in the building to take a few work calls before I was able to check in, which was a really nice perk. Also, close distance to many things around Chicago. I would stay here again!
Reviewed on Aug 21, 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
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The room was very nice and large. The beds were very comfortable. The views from our room were great.
Reviewed on Aug 21, 2026
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View all trips3 Night All inclusive vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
￥232,888
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,004 reviews)
Very Clean affordable stay near ORD. Shuttle runs every 30 minutes to ORD. We came in for a brief stay and found it to be clean and comfortable. The shuttle was very convenient.
Gibson's was very good next door so there is a great food option as well, but surounded by multiple other things.
Reviewed on Aug 21, 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.
Level Chicago Fulton Market
Downtown Chicago
￥314,960
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥374,326
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The room was very nice and large. The beds were very comfortable. The views from our room were great.
Reviewed on Aug 21, 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.
