Southwest Wisconsin Vacation Packages 2026 from $344

Southwest Wisconsin flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

$344

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

JW Marriott Chicago

Downtown Chicago

$467

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$459

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$558

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$606

per person

Apr 16 - Apr 20

found 12 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

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

$139 nightly

$161 total

Feb 15 - Feb 16

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

1400 Great Wolf Dr Baraboo WI

$149 nightly

$167 total

Feb 16 - Feb 17

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

655 N. Frontage Road Wisconsin Dells WI

Free Cancellation

Reserve now, pay when you stay

$50 nightly

$56 total

Feb 12 - Feb 13

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

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr Madison WI

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$71 total

Mar 13 - Mar 14

Total with taxes and fees

This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd Wisconsin Dells WI

$77 nightly

$86 total

Feb 23 - Feb 24

Total with taxes and fees

This hotel features an indoor pool and a lazy river. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Pet friendly

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Free Cancellation

Reserve now, pay when you stay

$55 nightly

$64 total

Feb 16 - Feb 17

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.

Pet friendly

Parking included

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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

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

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.

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.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $344. 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.