Southeast Wisconsin Vacation Packages 2026 from $976

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Your Southeast Wisconsin Vacation

Our Southeast Wisconsin vacation packages provide an affordable, easy and immersive way to enjoy everything this exciting destination has to offer. If it's distilleries and craft breweries and dining you're yearning for, this is the place to come. With so many things to see and do on a trip to Southeast Wisconsin, it can be tricky 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 top city worth adding to your itinerary is Lake Geneva. Be sure not to miss Geneva Lake and Walworth County Fairgrounds. Expedia has everything you need for planning your Southeast Wisconsin vacation. From accommodations and flights, to car rentals and activities, we know how to curate a travel experience like no other.

The Latest Southeast Wisconsin vacation packages

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

Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Save 100% on your flight

$976

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,164 reviews)

Reviewed on Aug 30, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$983

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (556 reviews)

Great! But parking was bad.

Reviewed on Aug 26, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$1,233

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,045 reviews)

Love the place

Reviewed on Aug 30, 2026

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$1,224

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,339 reviews)

Always an excellent experience, and convenient to everything in Fulton Market and West Loop.

Reviewed on Aug 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,100

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,654 reviews)

My stay was amazing, the view was spectacular- a self contained, day date to treat myself to the sites, sounds & view of Sweet Home Chicago! I booked a return visit for December before breakfast 😂

Reviewed on Aug 30, 2026

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Where to stay in Southeast Wisconsin

Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast 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 river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

1 out of top 10 points of interest in this area

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.

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.

A pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

East Town

East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.

Stay near popular Southeast 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 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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Milwaukee County Zoo

8.6/10 (799 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

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A wall of vintage motorcycle advertisements and models.

Harley-Davidson Museum

8.8/10 (1,541 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.

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A brightly lit Ferris wheel with multiple cabins at night.

Wisconsin State Fair Park

9.0/10 (217 reviews)

Enjoy an outing to Wisconsin State Fair Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

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A calm lake with sailboats docked on the left, surrounded by mountains and a clear sky.

Lake Como

8.8/10 (214 reviews)

Commune with nature and explore the great outdoors at Lake Como during your travels in Lake Geneva. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

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Baird Center

8.2/10 (522 reviews)

Learn about the events happening at Baird Center during your trip to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

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Southeast Wisconsin Hotel Deals

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$73 nightly

$85 total

Sep 1 - Sep 2

Total with taxes and fees

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

$166 nightly

$195 total

Sep 7 - Sep 8

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! (1,395 reviews)

"Loved the lake view."

Reviewed on Aug 29, 2026

See all 2,491 properties in Southeast 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.