Southwest Wisconsin Vacations from NT$29,314

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The Latest Southwest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (3,512 reviews)
Very nice staff, food is ok, location is good, beds are super comfy!

Reviewed on 2025/8/8

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (1,012 reviews)
The room is a little small for the price. However, it is a cute little hotel. The complimentary breakfast is barely average, but it's free. The staff was really nice. I appreciated how helpful they were when I asked questions. The fitness center is small barely has any equipment. Thankfully, it wasn't busy while I was in there. It's in a great spot to find nice places to eat and there is a Trader Joe's around the corner. Overall, it was a nice hotel. I would stay there again.

Reviewed on 2025/8/3

ACME Hotel Company

ACME Hotel Company

3.5 out of 5
Downtown Chicago
per person
Sep 22 - Sep 25
found 1 hour ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,739 reviews)
Central and walkable to the Magnificent Mile shopping, Navy Pier, Millenium Park, the Loop and many restaurants. Hotel is older but still comfortable. Parking available next door to hotel (public parking). Cute coffee shop and bakery in lobby and great tasting bar in hotel.

Reviewed on 2025/8/7

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 NT$1,198 per night from Sep 1 to Sep 2
NT$1,198
NT$1,345 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (2,320 reviews)
"Surprised with all the different type of hotels the facility had..all were friendly!"

Reviewed on 2025/8/6

Mt. Olympus Water & Theme Park Resort
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 NT$1,417 per night from Sep 1 to Sep 2
NT$1,417
NT$1,590 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,507 reviews)
"Great spot, walkable to downtown and close to many attractions."

Reviewed on 2025/8/4

Days Inn & Suites by Wyndham Wisconsin Dells
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
9.4/10 Exceptional! (2,950 reviews)
"Great location and excellent value. Having a restaurant and bar on site was a huge plus. Shuttle to the airport at 5 am was appreciated!"

Reviewed on 2025/8/5

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The Madison Concourse Hotel and Governor's Club
See all 3,666 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

Kalahari Indoor Waterpark

Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark

Frequently asked questions

How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible NT$29,314, 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.