Southwest Wisconsin Vacations from ￥248,500

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The Latest Southwest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥343,557, price is now ￥248,500 per person
￥248,500
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥353,710, price is now ￥268,396 per person
￥268,396
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
The place was in a great location, close to everything. I was traveling alone and felt very comfortable. The roof bar was gorgeous but the service was just ok up there.

Reviewed on Aug 28, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥358,844, price is now ￥278,143 per person
￥278,143
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on Aug 25, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥323,910, price is now ￥251,450 per person
￥251,450
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on Aug 26, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥409,499, price is now ￥319,112 per person
￥319,112
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
The Hotel is very convenient, but needs updating. The bathrooms are old, etc. The staff was very friendly and the dining options are excellent and very convenient given you’re in the middle of the airport.

Reviewed on Aug 26, 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
Madison showing a garden, a house and flowers

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 hotels in Downtown Madison

Find the Best Southwest Wisconsin Vacation Packages

Southwest Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is ￥6,626 per night from Sep 2 to Sep 3
￥6,626
￥7,436 total
Sep 2 - Sep 3
includes taxes & fees
6.8/10 (2,357 reviews)
"Bathtub and toilet not draining properly and mattress not the best. Other than that we had a great time"

Reviewed on Aug 25, 2025

Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
The price is ￥18,423 per night from Aug 31 to Sep 1
￥18,423
￥21,280 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (3,016 reviews)
"Governors Club access was definitely worth it. Staff were extremely friendly and helpful. Hotel was very quiet and clean. I only wish they had some outside sitting areas to be able to enjoy the amazing weather- but otherwise excellent. Very walkable as well to almost anything you wanted to do."

Reviewed on Aug 25, 2025

The Madison Concourse Hotel and Governor's Club
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is ￥7,135 per night from Sep 15 to Sep 16
￥7,135
￥8,009 total
Sep 15 - Sep 16
includes taxes & fees
Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,791 properties in Southwest Wisconsin
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

Cool street art in Madison, 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.

University of Wisconsin-Madison
Mt. Olympus Water and Theme Park

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.

Mt. Olympus Water and Theme Park
Capitol Building

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.

Capitol Square

Frequently asked questions

How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible ￥248,500, you can handcraft your own Southwest Wisconsin package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Southwest Wisconsin?
If you love scoring a bargain, bundle your bookings into a Southwest Wisconsin vacation package. Whether you're looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options globally to pick from. Fly with who you prefer, book a room where you like and save a tidy sum — now that's the ideal escape!
What are the top hotels in Southwest Wisconsin?
Chula Vista Resort, Trademark Collection by Wyndham and Adams Inn know how to make their guests feel at home in Wisconsin Dells. If your travel plans also include Baraboo, check out La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton and Days Inn & Suites by Wyndham Wisconsin Dells. Both are popular with travelers.
How far in advance should I book my Southwest Wisconsin vacation?
It all depends on the airline, but you can usually look up international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travelers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Southwest Wisconsin travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Southwest Wisconsin getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Southwest Wisconsin travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything together will make your trip planning easier. So why waste your time or money? Whether you're organizing a luxury city stay with your love or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Southwest Wisconsin Expedia vacation package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin vacation package?
Yes, it's possible to cancel your Southwest Wisconsin booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.