Southeast Wisconsin Vacation Packages 2026 from $300

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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.

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$300

per person

Dec 21 - Dec 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$783

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$376

per person

Dec 21 - Dec 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,841 reviews)

I didn’t like the fact that they said I would get a discount on being a senior citizen. The party lied and price was more

Reviewed on Oct 20, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$383

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

The first room I checked in to had the door not flushly closing, and looked like someone had pried their way into the room. I checked in at 2:30am after driving from the Green Bay Packers football game in Green Bay, and they insisted that I check out at 11am. After two or three calls, they managed to delay it to 12:30pm. They want a $100 an hour for every hour you stay in the room after 11am and they very aggressively enforce it. I did not pay this amount and won't be staying at this hotel again and recommend that they change their customer service approach or clients will be choosing other hotels.

Reviewed on Oct 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$433

per person

Jan 7 - Jan 13

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 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 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 Cathedral Square. 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 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 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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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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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

$84 nightly

$99 total

Nov 9 - Nov 10

Total with taxes and fees

8.6/10 Excellent! (1,553 reviews)

"Enjoyed the high floor room, & had housekeeping everyday I requested. Enjoyed the bar staff. Good food & drinks. A little bit of a dated hotel, but that's ok! We hope to return again next year- Great stay!"

Reviewed on Oct 21, 2026

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$87 nightly

$100 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

9.6/10 Exceptional! (2,417 reviews)

"Best hotel I've stayed at"

Reviewed on Oct 19, 2026

See all 2,451 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.