Southern Wisconsin Luxury Vacations
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Top Luxury vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
￥322,514
per person
Nov 2 - Nov 7
found 3 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥405,665
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.
Reviewed on Aug 17, 2026
Level Chicago Fulton Market
Downtown Chicago
￥379,826
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
L7 Chicago by LOTTE
Downtown Chicago
￥393,084
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
Very nice hotel, great location and price. We stayed one night for just a quick trip to the City. It was a bit noisy at night being right off a busy intersection but settled down as the night went on. Victoria at the front desk was fantastic! Thanks Victoria for being so welcoming. 😊
Reviewed on Aug 17, 2026
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View all trips5* Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
￥545,081
per person
Oct 7 - Oct 11
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.
Reviewed on Aug 16, 2026
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View all trips3 Night Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE
Downtown Chicago
￥317,097
per person
Sep 17 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
Very nice hotel, great location and price. We stayed one night for just a quick trip to the City. It was a bit noisy at night being right off a busy intersection but settled down as the night went on. Victoria at the front desk was fantastic! Thanks Victoria for being so welcoming. 😊
Reviewed on Aug 17, 2026
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See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
￥400,452
per person
Oct 7 - Oct 11
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Fairmont maybe an old hotel but it is well maintained hotel. With large rooms, great views of the skyline especially at night from our window. And Le Labo toiletries is a plus. Also Many great restaurants nearby
Reviewed on Aug 17, 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.
