Southeast Wisconsin Vacation Packages 2026 from $244

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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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$244

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,105 reviews)

The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well

Reviewed on Oct 14, 2026

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$483

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,347 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$476

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$498

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$441

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,163 reviews)

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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 waterfront cityscape at dusk with a calm river reflecting buildings and a bridge.

Wauwatosa

1 out of top 10 points of interest in this area

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 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.

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 cathedral at night with a large clock tower, surrounded by street lamps and a wet pavement.

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 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 relaxing area's lakeside and enjoy its top-notch restaurants.

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A motorcycle showroom with various models on display, including a red 1951 Big Twin.

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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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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The Rave-Eagles Club

8.0/10 (699 reviews)

You can enjoy a show at The Rave-Eagles Club 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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Southeast Wisconsin Hotel Deals

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

$93 nightly

$110 total

Nov 1 - Nov 2

Total with taxes and fees

8.6/10 Excellent! (1,531 reviews)

"The hotel was very good, the doorman and customer service at the desk were excellent. The hotel was very clean and we enjoyed our stay. I think the $36 for overnight parking was high, but other than that the stay was excellent. Everything we wanted to do (Pabst theatre, Usinger's sausage, riverwalk) ..."

Reviewed on Oct 14, 2026

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$64 nightly

$73 total

Nov 1 - Nov 2

Total with taxes and fees

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Fully refundableReserve now, pay when you stay

$119 nightly

$140 total

Nov 1 - Nov 2

Total with taxes and fees

See all 2,440 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.