Southwest Wisconsin Vacation Packages 2026 from $318

Southwest Wisconsin flight + hotel vacation packages

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

$318

per person

Jan 14 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.

Level Chicago Fulton Market

Downtown Chicago

$624

per person

Jan 23 - Jan 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Eurostars Magnificent Mile

Downtown Chicago

$796

per person

Jan 23 - Jan 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Villa Christina

Greater Grand Crossing

$514

per person

Jan 28 - Jan 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Hotel Riu Plaza Chicago

Downtown Chicago

$392

per person

Jan 14 - Jan 17

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.

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

$127 nightly

$146 total

Nov 16 - Nov 17

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

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Free Cancellation

$53 nightly

$61 total

Dec 4 - Dec 5

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

Natura Vue Resort & Boathouse

1015 River Rd Wisconsin Dells WI

$85 nightly

$95 total

Nov 15 - Nov 16

Total with taxes and fees

A marina and an indoor pool are featured at this smoke-free hotel. Enjoy a day at the beach water skiing, or relax with sun loungers. Enjoy a meal from the restaurant and perks like free WiFi.

Pool

Hot Tub

Natura Treescape Resort

400 County Road A Wisconsin Dells WI

$79 nightly

$89 total

Nov 20 - Nov 21

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

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road Wisconsin Dells WI

Free Cancellation

Reserve now, pay when you stay

$60 nightly

$67 total

Nov 15 - Nov 16

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

The Edgewater

1001 Wisconsin Place Madison WI

Free Cancellation

Reserve now, pay when you stay

$221 nightly

$255 total

Dec 13 - Dec 14

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Unwind with a drink at one of the 4 bars/lounges and enjoy perks like a free area shuttle.

Hot Tub

Spa

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.

Stay near popular Southwest Wisconsin attractions

A coastal landscape with autumn foliage, a beach, and a building.

Kalahari Indoor Waterpark

8.8/10 (445 reviews)

Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Southwest Wisconsin?

Vacation packages, which include hotels and flights in Southwest Wisconsin, start from $318. 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.