
Southern Wisconsin Cheap Vacations
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Top Cheap vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥265,634, price is now ¥210,174 per person
¥210,174
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The property is Great I got married there!
Reviewed on Sep 24, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥343,518, price is now ¥246,906 per person
¥246,906
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥399,230, price is now ¥289,662 per person
¥289,662
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,194, price is now ¥242,014 per person
¥242,014
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025

The Emily Hotel
Downtown Chicago
Price was ¥302,855, price is now ¥234,802 per person
¥234,802
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead
Reviewed on Sep 22, 2025
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View all trips5* Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥399,230, price is now ¥289,662 per person
¥289,662
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥373,586, price is now ¥297,150 per person
¥297,150
per person
Nov 17 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

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View all trips3 Night Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥373,498, price is now ¥291,684 per person
¥291,684
per person
Nov 17 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥373,586, price is now ¥297,150 per person
¥297,150
per person
Nov 17 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on Sep 8, 2025

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See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,194, price is now ¥242,014 per person
¥242,014
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥343,518, price is now ¥246,906 per person
¥246,906
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥399,230, price is now ¥289,662 per person
¥289,662
per person
Nov 29 - Dec 3
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025
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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.