Southwest Wisconsin Vacation Packages 2025/2026 from $202

Southwest Wisconsin flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$202

per person

Dec 12 - Dec 14

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.

The Westin Michigan Avenue Chicago

Downtown Chicago

$517

per person

Dec 23 - Dec 27

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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$282

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$689

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip non-stop 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.

Illinois Beach Hotel

Save 100% on your flight

$296

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Top Southwest Wisconsin hotels deals

The Madison Concourse Hotel and Governor's Club

1 W Dayton St, Madison, WI

$139 nightly

$161 total

Oct 12 - Oct 13

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

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr, Madison, WI

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$82 total

Oct 12 - Oct 13

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

Natura Treescape Resort

400 County Road A, Wisconsin Dells, WI

$65 nightly

$73 total

Oct 7 - Oct 8

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.

On private beach

Pool

Aloha Beach Resort

1370 E Hiawatha Dr, Wisconsin Dells, WI

$70 nightly

$79 total

Oct 7 - Oct 8

Total with taxes and fees

A private beach and an indoor pool are featured at this hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and perks like free WiFi.

On private beach

Pool

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road, Wisconsin Dells, WI

Free Cancellation

Reserve now, pay when you stay

$55 nightly

$62 total

Oct 7 - Oct 8

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

Motel 6 Madison, WI - East

4202 E Towne Blvd, Madison, WI

Free Cancellation

Reserve now, pay when you stay

$40 nightly

$47 total

Nov 2 - Nov 3

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

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.

Devil's Lake

Commune with nature and explore the great outdoors at Devil's Lake during your travels in Baraboo. Discover the entertainment venues in this family-friendly area, or seek out its hiking trails.

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $202. 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.