Southern Wisconsin Vacation Packages 2026 from $331

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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.

Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Save 100% on your flight

$331

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.6/10 Good! (2,711 reviews)

need your own parking spaces.

Reviewed on Aug 19, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$746

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$453

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,089 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$737

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

Save 100% on your flight

$384

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (3,942 reviews)

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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

2 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 Orpheum Theater or Overture Center for the Arts might round out your trip.

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 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.

Witches Gulch, Wisconsin Dells, Wisconsin

Lake Delton

1 out of top 10 points of interest in this area

If you're spending some time in Lake Delton, Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are top sights worth seeing.

Stay near popular Southern Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.

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

Mt. Olympus Water and Theme Park

7.4/10 (1,284 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.

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A park with a pond, trees, and a modern building with yellow and black colors.

EAA Aviation Museum

9.2/10 (245 reviews)

You can spend an afternoon studying the exhibits at EAA Aviation Museum in Oshkosh. Visit the area's shops or attend a sporting event.

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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 stone archway with inscriptions and statues, surrounded by greenery.

Camp Randall Stadium

9.0/10 (1,067 reviews)

Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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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 lakeside or experience the entertainment choices in this family-friendly area.

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Noah's Ark Waterpark

8.4/10 (959 reviews)

Enjoy the excitement at Noah's Ark Waterpark and find out why this is a popular amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

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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

$50 nightly

$56 total

Aug 30 - Aug 31

Total with taxes and fees

7/10 Good! (2,956 reviews)

"There were no street light on near entry and dirty entry and staircase. No drinking water facility . Other guests were doing party in general until 3 am morning making lots of di"

Reviewed on Aug 19, 2026

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$80 nightly

$93 total

Aug 20 - Aug 21

Total with taxes and fees

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Fully refundableReserve now, pay when you stay

$169 nightly

$191 total

Sep 7 - Sep 8

Total with taxes and fees

9.2/10 Wonderful! (1,390 reviews)

"I loved staying here. It is within walking distance to the center of Lake Geneva but it is also quiet in the evening. It is so calming to sit and look out on the lake before dinner. Would definitely return."

Reviewed on Aug 18, 2026

See all 7,688 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.