Southern Wisconsin Mountain Vacations
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Top Mountain vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥396,813, price is now ￥306,652 per person
￥306,652
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Excellent Staff,nice location,I'm would come again..
Reviewed on Jul 27, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥539,274, price is now ￥421,875 per person
￥421,875
per person
Sep 10 - Sep 17
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,271 reviews)
This hotel it’s a 10/10 I stayed in this place before and I totally love it. Rooms are super spacious,clean,good view,etc. Staff always helpful and very friendly. The only thing I wish they need is a pool but overall it’s an excellent place to stay.
Reviewed on Jul 26, 2026
The Emily Hotel
Downtown Chicago
Price was ￥446,236, price is now ￥355,220 per person
￥355,220
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
So this is what it's like to stay in a "tech-bro" hotel! No closet, just a chrome grid to hand my hoodie and messenger bag. (I actually didn't have either of these, so I felt the loss of a dresser/drawers.)
NOTHING to hang towels on in the bathroom. Would it kill them to have a couple of hooks?
Full bar, and I mean full--too bad I don't drink.
The beds were low, but the sheets and mattress was extremely comfortable. The resturant next to the hotel had great food.
Reviewed on Jul 27, 2026
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View all trips5* Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥523,276, price is now ￥427,836 per person
￥427,836
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)
Beautiful hotel and room!
Reviewed on Jul 26, 2026
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View all trips3 Night Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥476,196, price is now ￥365,624 per person
￥365,624
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Excellent Staff,nice location,I'm would come again..
Reviewed on Jul 27, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥403,166, price is now ￥336,040 per person
￥336,040
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,502 reviews)
$15 resort fee rebate did not cove one martini
Reviewed on Jul 27, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥396,813, price is now ￥306,652 per person
￥306,652
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Excellent Staff,nice location,I'm would come again..
Reviewed on Jul 27, 2026
The Emily Hotel
Downtown Chicago
Price was ￥446,236, price is now ￥355,220 per person
￥355,220
per person
Oct 12 - Oct 16
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
So this is what it's like to stay in a "tech-bro" hotel! No closet, just a chrome grid to hand my hoodie and messenger bag. (I actually didn't have either of these, so I felt the loss of a dresser/drawers.)
NOTHING to hang towels on in the bathroom. Would it kill them to have a couple of hooks?
Full bar, and I mean full--too bad I don't drink.
The beds were low, but the sheets and mattress was extremely comfortable. The resturant next to the hotel had great food.
Reviewed on Jul 27, 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.
