Southwest Wisconsin Vacations from ￥158,343
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Southwest Wisconsin Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥230,232, price is now ￥158,343 per person
￥158,343
per person
Nov 13 - Nov 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Overall, the stay was enjoyable. Nice facilities. We really enjoyed the Rooftop restaurant on our first night. Suggestions for improvement include offering a variety of pillow options (preferably down alternatives), a microwave in the room, and vending or self-serve options for water or snacks. My son had to go to a 7-Eleven for water and Gatorade (even though we are club members). The night staff informed me that only one bottle of water was complimentary. I would have gladly paid for one, but that apparently wasn't an option either.
Reviewed on Sep 3, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥328,496, price is now ￥222,669 per person
￥222,669
per person
Nov 13 - Nov 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep 2, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ￥403,008, price is now ￥280,014 per person
￥280,014
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
Friendly and helpful staff
Reviewed on Sep 3, 2025
The Langham, Chicago
Downtown Chicago
Price was ￥334,268, price is now ￥245,994 per person
￥245,994
per person
Nov 13 - Nov 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
Where to stay in Southwest Wisconsin
Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
Downtown Madison
The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.
Find the Best Southwest Wisconsin Vacation Packages
Southwest Wisconsin Hotel Deals
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is ￥6,679 per night from Sep 4 to Sep 5
￥6,679
￥7,496 total
Sep 4 - Sep 5
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is ￥18,572 per night from Sep 14 to Sep 15
￥18,572
￥21,451 total
Sep 14 - Sep 15
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is ￥9,464 per night from Sep 21 to Sep 22
￥9,464
￥10,931 total
Sep 21 - Sep 22
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Southwest Wisconsin
University of Wisconsin-Madison
Enjoy the collegiate vibe around University of Wisconsin-Madison, a top college in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Mt. Olympus Water and Theme Park
Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
Capitol Square
You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.
Other vacations you might like
Expedia's Latest Trends
Flights
General
- Visit Oahu
- Visit Catalina Island
- Visit Long Island
- Visit Florida Panhandle
- Visit Nantucket Island
- Visit Aleutian Islands
- Visit Northern Arkansas
- Visit Upstate New York
- Visit Greenville - Spartanburg
- Visit Silicon Valley
- Visit Whidbey Island
- Visit Bay Area
- Visit Cape Cod
- Visit Glen Canyon National Recreation Area
- Visit Napa Valley
- Visit Cape May - Wildwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.