Southern Wisconsin Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
Photo by Evae
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Luxury vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥1,181,084, price is now ￥913,977 per person
￥913,977
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,283 reviews)
I mean….loved this place! It was clean, the staff were very helpful, the rooftop bar is to die for.
Reviewed on Jul 1, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥1,169,453, price is now ￥906,070 per person
￥906,070
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,392 reviews)
Gorgeous property, excellent view and room was very clean. Staff were friendly and helpful.
Reviewed on Jun 21, 2026
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ￥1,194,984, price is now ￥937,844 per person
￥937,844
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,524 reviews)
Felt it was more like a 3 star rather than 4 star. Comparable to a Holiday express. But the breakfast was very good.
Reviewed on Jun 29, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥895,568, price is now ￥768,496 per person
￥768,496
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is very clean
Good air conditioning
The staff is great
The bar at the restaurant is very good
The location is the best in Chicago
Fancy neighborhood
Reviewed on Jun 30, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips3 Night Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥129,289, price is now ￥100,034 per person
￥100,034
per person
Aug 16 - Aug 19
found 15 hours ago
Roundtrip flight included
Los Angeles (QLA) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥103,972, price is now ￥83,353 per person
￥83,353
per person
Aug 16 - Aug 19
found 15 hours ago
Roundtrip flight included
Los Angeles (QLA) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.
Reviewed on Jul 1, 2026
Don't see what you're looking for?
See all available trips from Los Angeles to Southern Wisconsin
View all trips4 Night Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥709,500, price is now ￥599,950 per person
￥599,950
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
