Southwest Wisconsin Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Southwest Wisconsin Vacation
Choose a vacation package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. La Crosse is another favourite city with Southwest Wisconsin travellers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Centre. From the moment you book your Southwest Wisconsin vacation to when you get back home, Expedia will take care of you every step of the way.
Top Southwest Wisconsin Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
CA $1,130
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
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
2 out of top 10 points of interest in this area
The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Overture Center for the Arts or Orpheum Theater might round out your trip.
Lake Delton
1 out of top 10 points of interest in this area
If you're spending some time in Lake Delton, Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are top sights worth seeing.
Historic Downtown La Crosse
1 out of top 10 points of interest in this area
The abundant dining options and stunning river views are top of the list for many visitors to Historic Downtown La Crosse. A stop by La Crosse Center or Oktoberfest Grounds might round out your trip.
Capitol
While visiting Capitol, you might make a stop by sights like Wisconsin State Capitol and Overture Center for the Arts.
Monona
Situated on Lake Monona's southeastern shore, this Madison suburb boasts the historic Indian Mounds Park, a site on the National Register of Historic Places.
Ready to book your vacation to Southwest Wisconsin?
Southwest Wisconsin Hotel Deals
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
CA $74
CA $83 total
Oct 12 - Oct 13
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
CA $174
CA $201 total
Sep 27 - Sep 28
includes taxes & fees
Natura Treescape Resort
400 County Road A Wisconsin Dells WI
CA $73
CA $98 total
Oct 16 - Oct 17
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.
Stay near popular Southwest Wisconsin attractions
Mt. Olympus Water and Theme Park
7.4/10 (1,284 reviews)
Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.
Camp Randall Stadium
9.0/10 (1,067 reviews)
Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Kalahari Indoor Waterpark
8.8/10 (445 reviews)
Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.
Noah's Ark Waterpark
8.4/10 (959 reviews)
Bring your family to Noah's Ark Waterpark and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
Chula Vista Waterparks
7.6/10 (630 reviews)
Enjoy a stop at Chula Vista Waterparks, an entertaining place to visit in Wisconsin Dells. While you're in the area, stroll along the riverfront.
Alliant Energy Center
8.6/10 (944 reviews)
Catch an event at Alliant Energy Center during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
La Crosse Center
8.8/10 (441 reviews)
Catch an event at La Crosse Center during your trip to La Crosse. Wander the area's riverfront or simply enjoy one of its lively bars.
Frequently asked questions
How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible CA $1,098, 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.
Explore a world of travel with Expedia
- Voyageur Inn and Conference Center
- Americinn & Suites By Wyndham Baraboo Event Center
- Waterpark Hotels in Wisconsin Dells
- Motels in Arena
- Pet-Friendly Hotels in Wisconsin Dells
- Americinn by Wyndham Boscobel
- Hotels near Mt. Olympus Water and Theme Park
- Hotels near Outlets at The Dells
- Cheap Hotels in Viola
- Hill Point Hotels
- Wilderness Resort
- Wild Rose Ranch Guest Cabin
- Muscoda Hotels
- Cottages in Sextonville
- Pet-Friendly Hotels in Southwest Wisconsin
- Great Wolf Lodge Wisconsin Dells
- Secluded cabin on 75 acres 360 views cedar hot tub infrared sauna outdoor Shower
- Motels in Viola
- Adults Only Resorts & in Wisconsin Dells
- Hampton Inn & Suites at Wisconsin Dells Lake Delton
- Fletcher Hotels in Ontario
- Boscobel Hotels
- Romantic Hotels in Ontario
- Cabin Rentals in Basswood
- Holiday Inn Express Wisconsin Dells by IHG
- Three Bedroom Deluxe Luxury Condo
- 5 Star Hotels in Ontario
- Baraboo Hotels
- Resorts in Lime Ridge
- Spacious Multi
- Brand New Cabin For Getaway Vacation
- B&B in La Farge
- Rock Springs Hotels
- Hilton Hotels in Reedsburg
- Winery Hotels in Southwest Wisconsin
- Hillsboro Hotels
- Beautiful Log Cabin Near Devil’s Lake
- Cabin Rentals in Ontario
- Hotels near Noah's Ark Waterpark
- Elroy Hotels
- Lake Delton Hotels
- Spring Green Hotels
- B&B in Gays Mills
- Wisconsin Dells Hotels
- Gays Mills Hotels
- The Round Barn Lodge
- Club Wyndham Glacier Canyon
- Resorts in Wisconsin Dells
- Glacier Canyon Resort With Free access to WaterParks and other Amenities
- Farmstay in Reedsburg
- Cabin Rentals in Gotham
- Geodesic Dome House: 18 Acres on Baraboo River!
- 3 Star Hotels in Muscoda
- Ramada by Wyndham Richland Center
- 2 Bedroom Presidential Condo
- Luxury Hotels in Reedsburg
- Pine Ridge Motel
- Cheap Hotels in Wisconsin Dells
- Polynesian Hotel & Suites Wisconsin Dells/Lake Delton
- Viola Hotels
- Historic Wisconsin Retreat on 26
- Soldiers Grove Hotels
- Luxury Hotels in Wisconsin Dells
- Atlantis Family Waterpark Hotel
- Ramada by Wyndham Wisconsin Dells
- Cabin Rentals in La Valle
- Ho
- Wingate by Wyndham Wisconsin Dells Waterpark
- Vacation Homes in Bell Center
- Burke Vacations
- Wisconsin Dells Vacations
- Visit Lake Delton
- Cuba City Vacations
- Tower Hill State Park
- Wizard Quest
- Lost Temple
- Kalahari Indoor Waterpark
- Noah's Ark Waterpark
- Verona Vacations
- Woodside Wisconsin Dells Center Dome
- Visit Southwest Wisconsin
- Prairie Du Chien Vacations
- Madison Vacations
- Arena Vacations
- Mt. Olympus Water and Theme Park
- Visit Wisconsin Dells
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
