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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $983, price is now $639 per person
$639
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,283, price is now $888 per person
$888
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was $2,237, price is now $1,548 per person
$1,548
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,919, price is now $1,328 per person
$1,328
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,722, price is now $1,258 per person
$1,258
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Top Southwest Wisconsin hotels 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
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Mar 29 - Mar 30
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
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $167 total per night
$167 total
Apr 5 - Apr 6
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 seasonal outdoor pool, and unwind with a drink at the bar/lounge.
Pool
Hot Tub
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
$50 nightly
The price is $56 total per night
$56 total
Apr 5 - Apr 6
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
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
$126 nightly
The price is $146 total per night
$146 total
Mar 28 - Mar 29
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
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $122 total per night
$122 total
Mar 25 - Mar 26
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 and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Atlantis Family Waterpark Hotel, an Ascend Collection Hotel

Atlantis Family Waterpark Hotel, an Ascend Collection Hotel

3 out of 5
1570 Wisconsin Dells Pkwy Wisconsin Dells WI
Free Cancellation
$71 nightly
The price is $80 total per night
$80 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel's 3 indoor pools and seasonal outdoor pool are among the featured amenities. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking and 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

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
Historic Arched Entry to Camp Randall Stadium

Camp Randall Stadium

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
Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

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 riverfront or experience its entertainment choices.

Mt. Olympus Water and Theme Park

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?
Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $639. 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

Devil's lake state park in Wisconsin! The "The Ice Age Scenic trail loop", a short part of the National scenic trail. If you're around the area,make sure to put this park and specifically this trail on your check list! It is a beautiful hike,with a very special view of a range of deep to light colors of blue lake surrounding by 500 foot high quartzite bluffs,which was created by glacier. This trail is 14 mile trek with many offered amenities; such as fishing, boat ramp, swimming, and bird watching, there is plenty to keep everyone having fun. Best of all-this park is pet friendly! #hiking #travel #crosscountry #devilslake #wisconsin #statepark #backpacking
Ice castle at Wi Dells.
Along the CCC Trail, east wall.
Madison Union terrace. Madison has so many things to do- rent out some boats, canoes, go hiking, walk the trails, or sit by the water and enjoy the beauty!
Cheese days

Explore More Ways to Travel with Travelocity