Southern Wisconsin Vacation Packages 2025 from $214

Southern Wisconsin flight + hotel vacation packages

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

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

per person

Aug 24 - Aug 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Palmer House a Hilton Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 24 - Aug 26

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 historic 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 limo/town car service.

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

per person

Aug 24 - Aug 26

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 express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 24 - Aug 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

per person

Aug 24 - Aug 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out 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

Jun 8 - Jun 9

Total includes 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

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$254 nightly

$283 total

Jun 8 - Jun 9

Total includes 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

Harbor Shores on Lake Geneva

300 Wrigley Dr, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$175 total

Jun 3 - Jun 4

Total includes taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

$205 nightly

$242 total

Jun 29 - Jun 30

Total includes 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

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

Jun 3 - Jun 4

Total includes 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

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street, Milwaukee, WI

$127 nightly

$150 total

Jun 8 - Jun 9

Total includes 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 24-hour gym and free buffet breakfast each morning.

Pool

Hot Tub

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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 $214. 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.