Southern Wisconsin Vacation Packages 2025/2026 from $258

Southern Wisconsin flight + hotel vacation packages

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

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

Save 100% on your flight

$258

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

The Westin Michigan Avenue Chicago

Downtown Chicago

$638

per person

Dec 23 - Dec 28

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$383

per person

Nov 14 - Nov 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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$670

per person

Nov 28 - Dec 3

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, laundry facilities, and concierge services are also on offer.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$562

per person

Nov 28 - Dec 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Top Southern 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

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

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$258 total

Oct 16 - Oct 17

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool 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. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Pool

Spa

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.

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$215 total

Oct 8 - Oct 9

Total with taxes and fees

This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining.

Pool

Hot Tub

Natura Treescape Resort

400 County Road A, Wisconsin Dells, WI

$65 nightly

$73 total

Oct 6 - Oct 7

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

Potawatomi Hotel & Casino

1611 West Canal Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$171 total

Oct 7 - Oct 8

Total with taxes and fees

A casino, 7 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking. Free self parking, a 24-hour business center, and a coffee shop are also offered.

Parking included

Free WiFi

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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

4.5/5(872 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

4/5(146 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.

Harley-Davidson Museum

4.5/5(337 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Frequently asked questions

How much are vacation packages to Southern Wisconsin?

Prepare to be pleasantly surprised — you can recharge your batteries in Southern Wisconsin for just $258. Allow Travelocity to save you time and money with our excellent vacation packages. With flights, hotels and tours all ready to go, why wait any longer?

Where can I get the best vacation package deals for Southern Wisconsin?

With at least 400 airlines and 1,000,000 properties all over the world, it's hard to go past Travelocity. Make the most of our comprehensive range and create your dream Southern Wisconsin package deal. Isn't it great when trip planning is that easy?

Why should I book my Southern Wisconsin vacation bundle via Travelocity?

We have experiences and destinations for every type of traveler, top-quality service and 24/7 support. In addition to that, we'll match any cheaper price you discover with our Price Match Guarantee.

Can I save money on my Southern Wisconsin car rental if I combine it with my hotel or flight?

Combining your bookings into a Southern Wisconsin vacation package will leave you with some serious savings. Bundle a flight and car; a flight, hotel and car; or a car and hotel. There's no better way to discover the greater Southern Wisconsin area than with your own rental car. You can also add tours and experiences to your Travelocity package.

Which airport is best for Southern Wisconsin?

The top airports for Southern Wisconsin are General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN).

What is there to do in Southern Wisconsin?

Southern Wisconsin boasts hidden gems around every turn, however ensure you get to Gardens of the Fox Cities and American Family Field while you're here. These attractions are a must-see.