Southwest Wisconsin Vacation Packages 2026 from $279

Southwest Wisconsin flight + hotel vacation packages

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

The Drake

Downtown Chicago

Save 100% on your flight

$279

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A coffee shop, limo/town car service, and a grocery/convenience store are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$958

per person

Mar 14 - Mar 21

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$472

per person

Mar 13 - Mar 15

found 20 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$402

per person

Feb 13 - Feb 17

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$439

per person

Mar 13 - Mar 15

found 20 hours ago

Roundtrip flight included

Charlotte (CLT) 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

Dec 28 - Dec 29

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

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$122 total

Dec 25 - Dec 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

Hampton Inn & Suites Madison-West

483 Commerce Dr Madison WI

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$83 total

Jan 9 - Jan 10, 2026

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

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

Jan 5 - Jan 6, 2026

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

Polynesian Hotel & Suites Wisconsin Dells/Lake Delton

857 N Frontage Rd Wisconsin Dells WI

$77 nightly

$86 total

Dec 30 - Dec 31

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

Tru by Hilton Madison West, WI

8102 Watts Rd. Madison WI

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$75 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Breakfast included

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

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.

Capitol Square

You can find out about the history of Madison with a visit to Capitol Square. Visit the area's shops, or simply enjoy its restaurants.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $279. 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.