Deals on vacations and trips to Southwest Wisconsin

Save when you book Southwest Wisconsin package deals

Choose two or more items and save on your trip:

Southwest Wisconsin flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This smoke-free hotel features 2 restaurants, 4 beach bars, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A nightclub, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and limo/town car service.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Southwest Wisconsin hotel deals

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 $139 per night
$139
per night
Jun 16 - Jun 17
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Hot Tub
Pet friendly
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Free Cancellation
Reserve now, pay when you stay
The price is $25 per night
$25
per night
May 29 - May 30
Free water park access and a lazy river are featured at this smoke-free resort. Bring the family and enjoy the children's pool, waterslide, and playground. There's a restaurant and a bar/lounge for dining and drinks, and also a seasonal outdoor pool on site.
Pool
Parking available
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue, Madison, WI
Free Cancellation
Reserve now, pay when you stay
The price is $150 per night
$150
per night
May 29 - May 30
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. Enjoy the spa tub and conveniences like a 24-hour front desk and laundry facilities.
Hot Tub
Breakfast included
Natura Treescape Resort

Natura Treescape Resort

2.5 out of 5
400 County Road A, Wisconsin Dells, WI
The price is $59 per night
$59
per night
May 29 - May 30
A private beach, 2 indoor pools, and 2 spa tubs are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
Hot Tub
Pool
Atlantis Family Waterpark Hotel, Ascend Hotel Collection

Atlantis Family Waterpark Hotel, Ascend Hotel Collection

3 out of 5
1570 Wisconsin Dells Pkwy, Wisconsin Dells, WI
Free Cancellation
Reserve now, pay when you stay
The price is $79 per night
$79
per night
May 29 - May 30
This smoke-free hotel's free water park and 3 indoor pools are some of the highlights. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Hot Tub
Pool
Chula Vista Resort, Trademark Collection by Wyndham

Chula Vista Resort, Trademark Collection by Wyndham

3.5 out of 5
2501 River Rd, PO Box 30, Wisconsin Dells, WI
Free Cancellation
Reserve now, pay when you stay
The price is $162 per night
$162
per night
May 29 - May 30
This resort features a golf course, free water park access, and 5 restaurants. There's fun for all ages with a lazy river and mini golf, and barbecue grills are available on site. Enjoy the 3 spa tubs and perks like free WiFi.
Hot Tub
Pet friendly
Don't see what you're looking for?
See all available properties in Southwest Wisconsin
View all properties
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.

Popular places to visit

Image for University of Wisconsin-Madison

University of Wisconsin-Madison

4.5/5(872 reviews)

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
Image for Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

4/5(146 reviews)

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
Image for Devil's Lake State Park

Devil's Lake State Park

4.5/5(185 reviews)

Explore the great outdoors at Devil's Lake State Park, a lovely green space in Wisconsin Dells. Stroll along the lakeside or visit the fun-filled waterparks in this family-friendly area.

Devil's Lake State Park

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?
With deals starting at just $470, hotel and flight packages are a fabulous way to make your vacation budget stretch further. Southwest Wisconsin, here you come!
Where can I get the best vacation package deals for Southwest Wisconsin?
You’ll find a tempting selection of Southwest Wisconsin package deals on Travelocity. With 400 airlines and 1,000,000 properties around the globe, organizing your ultimate getaway will be a piece of cake.
Why should I book my Southwest Wisconsin vacation package with Travelocity?
We take the hassle out of travel planning. Whether you’re after a new destination to wander around or want to ensure you get the best price on offer, we’re here to assist. Our 24/7 customer support, top-quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Will I save money on my Southwest Wisconsin car rental if I bundle it with my hotel or flight?
You sure can with our Southwest Wisconsin vacation packages. With one of these, there are lots of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and watch your savings start to pile up. With your own set of wheels, all the key sights in and around Southwest Wisconsin are a memorable road trip away.
What is the best time of year to go to Southwest Wisconsin?
If you love wandering wisely, is a terrific time to do it. That’s when you’ll find hotel rates are at their most affordable. In contrast, prices are at their highest in . June, July and August are the most popular times to stay in Southwest Wisconsin, so expect long lines for top attractions. Hoping to travel outside the busy season? You’ll find fewer crowds in November, December and January.
Which airport is best for Southwest Wisconsin?
If the plan is to fly into Southwest Wisconsin, chances are you’ll be touching down at Dane County Regional Airport (MSN) or La Crosse Municipal Airport (LSE).