Southeast Wisconsin Vacation Packages 2026 from $471

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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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$471

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Location and facility was very nice

Reviewed on Sep 7, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$571

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Breakfast had some cold cuts, but for a vegan there wasn't much more options than your standard US continental. The TV (which turns on automatically every time you enter the room - very annoying) was the worst setup I've seen in a hotel, the connection to cast wasn't working because the TV wasn't connected to wifi, the remote was weird (no volume/channel controls). Lobby was nauseatingly over-fragranced, makes me wonder what horrible scent they're trying to cover up. Tried to use the stairs instead of the slow elevators and couldn't get out on the 2nd floor for breakfast since the stair exits are locked. Overall fair to ok but missing the attention to detail that would've been nice at the price point. I definitely wouldn't stay for business travel.

Reviewed on Sep 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,029

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

The view is stunning! Just a heads up for those without a car: it’s quite a walk even to the bus terminal, which can be pretty exhausting after a long day of exploring.

Reviewed on Sep 9, 2026

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

$1,417

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$525

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Old,

Reviewed on Sep 8, 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

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 boat named "Vista King" on a river with a building featuring fish decorations in the background.

Westown

2 out of top 10 points of interest in this area

While visiting Westown, you might make a stop by sights like Miller High Life Theatre and UW–Milwaukee Panther Arena.

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 Southeast 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 church with two tall spires and a clock tower.

Marquette University

8.8/10 (968 reviews)

Walk around the campus at Marquette University 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 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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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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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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Mayfair Mall

8.4/10 (878 reviews)

You can search for that perfect souvenir at Mayfair Mall 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

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

$194 nightly

$229 total

Sep 27 - Sep 28

Total with taxes and fees

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$78 nightly

$90 total

Sep 10 - Sep 11

Total with taxes and fees

8/10 Very Good! (1,567 reviews)

"Clean, friendly staff, room was nice. And the price was right."

Reviewed on Sep 9, 2026

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Fully refundableReserve now, pay when you stay

$144 nightly

$163 total

Oct 6 - Oct 7

Total with taxes and fees

9.2/10 Wonderful! (1,430 reviews)

"We paid more for a lake view but it was worth it. The room was clean, staff were friendly, and the room looked updated since the last time we’d been there."

Reviewed on Sep 9, 2026

See all 2,487 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.