Southwest Wisconsin Vacation Packages 2026 from $509

Southwest Wisconsin flight + hotel vacation packages

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

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$509

per person

Aug 27 - Aug 29

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. 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.

Viceroy Chicago

Downtown Chicago

Save 100% on your flight

$902

per person

Aug 19 - Aug 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$823

per person

Aug 19 - Aug 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

$626

per person

Aug 27 - Aug 29

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.

The Royal Sonesta Chicago River North

Downtown Chicago

Save 100% on your flight

$584

per person

Jul 19 - Jul 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

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

Jun 14 - Jun 15

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.

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road Wisconsin Dells WI

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$84 total

Jun 1 - Jun 2

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.

Great Wolf Lodge Wisconsin Dells

1400 Great Wolf Dr Baraboo WI

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$167 total

Jun 1 - Jun 2

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.

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr Madison WI

Free Cancellation

Reserve now, pay when you stay

$54 nightly

$63 total

Jun 7 - Jun 8

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.

Natura Treescape Resort

400 County Road A Wisconsin Dells WI

$89 nightly

$100 total

Jun 1 - Jun 2

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.

Best Western Plus InnTowner Madison

2424 University Avenue Madison WI

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$150 total

Jun 1 - Jun 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

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $509. 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.