Southwest Wisconsin Vacation Packages 2025 from $406

Southwest Wisconsin flight + hotel vacation packages

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

Super Sleep Inn By OYO I-80 Princeton

per person

Sep 3 - Sep 8

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

An indoor pool, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Harrah's Joliet Casino & Hotel

Save 100% on your flight

per person

Aug 15 - Aug 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (CHI)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Blue Chip Casino Hotel and Spa

Save 100% on your flight

per person

Aug 3 - Aug 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

This hotel features a casino, a full-service spa, and 3 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Enjoy the 2 hot tubs and indoor pool, and unwind with a drink at the bar/lounge.

Top Southwest Wisconsin hotels deals

The Madison Concourse Hotel and Governor's Club

1 W Dayton St, Madison, WI

Free Cancellation

Reserve now, pay when you stay

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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

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Free Cancellation

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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

Grand Marquis Waterpark Hotel & Suites

840 Wisconsin Dells Parkway South, Wisconsin Dells, WI

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Free water park access and an indoor pool are featured at this smoke-free hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Pool

Parking included

DoubleTree by Hilton Madison East

4402 E Washington Ave, Madison, WI

Free Cancellation

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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

SpringHill Suites Wisconsin Dells

461 Wisconsin Dells Parkway, Wisconsin Dells, WI

Free Cancellation

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This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Great Wolf Lodge Wisconsin Dells

1400 Great Wolf Dr, Baraboo, WI

Free Cancellation

Reserve now, pay when you stay

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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

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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

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.

Mt. Olympus Water and Theme Park

4/5(146 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.

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.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $406. 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.