Southeast Wisconsin Vacations from $482

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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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$482
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight
$630
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$981
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations. Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay. The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service. This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨

Reviewed on Sep 18, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$705
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (3,012 reviews)
Room was nice and spacious

Reviewed on Sep 18, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$1,251
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,512 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 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 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 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 sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.
Photo by trenton.badillo

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.
See properties
A church with two tall spires and a clock tower.
Photo by ‎‎Debra Fischer

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 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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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

The Pfister Hotel

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI
$194 nightly
$229 total
Sep 20 - Sep 21
Total with taxes and fees
The Pfister Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$74 nightly
$85 total
Oct 6 - Oct 7
Total with taxes and fees
AmericInn by Wyndham Brookfield
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
$110 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Regency Milwaukee
See all 2,479 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.

Find the Best Southeast Wisconsin Vacation Packages

Southeast Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)

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