Southern Wisconsin Vacation Packages 2026 from $590

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Your Southern Wisconsin Vacation

Our Southern Wisconsin vacation packages provide an easy, affordable and immersive way to experience everything this incredible destination has to offer. If it's distilleries and craft breweries and dining you're after, this is the place to be. With so much to see and do on a trip to Southern Wisconsin, it can be hard to know where to begin. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another city worthy of a spot on your itinerary is Wisconsin Dells. Be sure not to miss Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Expedia is a one-stop shop when it comes to organizing your Southern Wisconsin vacation. From hotels and flights, to car rentals and more, we know how to curate a travel experience like no other.

The Latest Southern Wisconsin vacation packages

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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$590

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

Amazing place to stay in Chicago!

Reviewed on Sep 18, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$760

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Had to request towels three times throughout the day before brought up. Thermostat stopped working, maintenance came and “fixed”, it stopped again in the middle of night spent a stuffy, hot night’s sleep. Shower drain clogged, informed front desk, maintenance never came that day. Glad we checked out the next day before anything else went wrong. Spend your $ somewhere else!

Reviewed on Sep 18, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

$1,047

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$630

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.6/10 Excellent! (1,001 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$737

per person

Nov 23 - Nov 27

found 3 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

This place was 10/10. The room was extremely clean. Had everything you needed. Even a washer and dryer. The staff were very helpful and friendly. They have a cute children’s area. The amenities floor was amazing and comfortable. Great area to walk to dinning and shopping and the oak st beach. We are walkers so while nothing was right around the corner we could walk to many sights like the river walk, the bean, chicago 360, all the stores.

Reviewed on Sep 17, 2026

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Where to stay in Southern Wisconsin

Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern Wisconsin

A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

A large domed building surrounded by modern cityscape and a body of water.

Downtown Madison

1 out of top 10 points of interest in this area

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Overture Center for the Arts or Orpheum Theater might round out your trip.

A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.

A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

Stay near popular Southern Wisconsin attractions

A sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.

American Family Field

9.0/10 (2,832 reviews)

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

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A cityscape with a variety of buildings, including a prominent white structure with a curved roof, a tall tower, and a mix of older and modern architecture.

Fiserv Forum

9.2/10 (2,312 reviews)

Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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A water park with a large Ferris wheel and a water slide.

Mt. Olympus Water and Theme Park

7.4/10 (1,284 reviews)

Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

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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.

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Noah's Ark Waterpark

8.4/10 (959 reviews)

Bring your family to Noah's Ark Waterpark and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

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The House on the Rock

9.4/10 (246 reviews)

You can find out about the history of Spring Green when you stop by The House on the Rock. You can enjoy the coffeehouses while in the area.

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Chula Vista Waterparks

7.6/10 (630 reviews)

Enjoy a stop at Chula Vista Waterparks, an entertaining place to visit in Wisconsin Dells. While you're in the area, stroll along the riverfront.

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Southern Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road Wisconsin Dells WI

Fully refundableReserve now, pay when you stay

$53 nightly

$59 total

Sep 19 - Sep 20

Total with taxes and fees

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

$194 nightly

$229 total

Sep 20 - Sep 21

Total with taxes and fees

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI

Fully refundableReserve now, pay when you stay

$139 nightly

$161 total

Sep 20 - Sep 21

Total with taxes and fees

9.4/10 Exceptional! (4,171 reviews)

"The carpet meats to be replaced in all the rooms. Looks dirty. Bedding was way too warm. Should have lighter options."

Reviewed on Sep 18, 2026

See all 7,754 properties in Southern Wisconsin

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.