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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,200, price is now $717 per person
$717
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,673, price is now $927 per person
$927
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,105, price is now $1,280 per person
$1,280
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $750 per person
$750
per person
Sep 3 - Sep 8
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. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $828 per person
$828
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Top Southwest Wisconsin hotels deals

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
$105 nightly
The price is $118 total per night
$118 total
Jul 16 - Jul 17
Total with taxes and fees
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
Restaurant
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
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Jul 5 - Jul 6
Total with taxes and fees
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.
Pool
Hot Tub
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
$104 nightly
The price is $120 total per night
$120 total
Jul 1 - Jul 2
Total with taxes and fees
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 hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
Dellshire Resort

Dellshire Resort

3.5 out of 5
2277 Wisconsin Dells Pkwy Wisconsin Dells WI
$179 nightly
The price is $201 total per night
$201 total
Jul 5 - Jul 6
Total with taxes and fees
This smoke-free hotel features 3 restaurants, 3 indoor pools, and a hot tub. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Hot Tub
Natura Treescape Resort

Natura Treescape Resort

2.5 out of 5
400 County Road A Wisconsin Dells WI
$129 nightly
The price is $145 total per night
$145 total
Jul 5 - Jul 6
Total with taxes and fees
A private beach, 2 indoor pools, and 2 hot tubs are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the seasonal outdoor pool and perks like free WiFi.
On private beach
Pool
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
$169 nightly
The price is $190 total per night
$190 total
Jul 8 - Jul 9
Total with taxes and fees
Free water park access, 3 restaurants, and 6 indoor pools are all featured at this smoke-free resort. Bring the family and enjoy the children's pool, waterslide, and arcade/game room. Enjoy the 2 hot tubs and perks like free WiFi.
Pool
Hot Tub
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

A water park with a large Ferris wheel and a water slide.

Mt. Olympus Water and Theme Park

3.5/5(148 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 lakeside or experience its entertainment choices.

Mt. Olympus Water and Theme Park
A mural with a skeleton, a dragon, and various figures.

University of Wisconsin-Madison

4.5/5(895 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
A stone archway with inscriptions and statues, surrounded by greenery.

Camp Randall Stadium

4.5/5(313 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.

Camp Randall Stadium

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?
Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $717. Turn your travel dreams into reality and book your trip with Travelocity today.
Where can I get the best vacation package deals for Southwest Wisconsin?
There are terrific Southwest Wisconsin package deals waiting for you with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep this in mind the next time you're ready to check another destination off the old bucket list.
Why should I purchase my Southwest Wisconsin vacation bundle with Travelocity?
We've got 24/7 customer support, excellent service and a Price Match Guarantee. Life is one big journey — and we have amazing destinations for you to journey to in all four corners of the globe. Roam with us and your wallet will thank you for it.
Can I save on my Southwest Wisconsin car rental if I combine it with my hotel or flight?
You 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 see the savings start to pile up. With a rental car, all the popular attractions around Southwest Wisconsin are just a road trip away.
Which airport is best for Southwest Wisconsin?
Southwest Wisconsin has two main hubs — Dane County Regional Airport (MSN) and La Crosse Municipal Airport (LSE).
What is there to do in Southwest Wisconsin?
Southwest Wisconsin has hidden gems around every corner, but make sure you get to Mt. Olympus Water and Theme Park and The House on the Rock during your stay. These attractions are very popular with visitors to the region.

Photos of local treasures

Browse Southwest Wisconsin vacation photos for more inspiration

A lake surrounded by lush green hills and a rocky cliff.
A vast expanse of ice with a central peak and radiating ice formations.
A rocky cliff overlooking a calm lake surrounded by dense forest.
Three colorful chairs on a dock overlooking a calm lake at sunset.
A parade float with a Cheese Day logo, featuring a cow and a man in a chef's outfit.

Explore More Ways to Travel with Travelocity