Southeast Wisconsin Vacation Packages
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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.
Top Southeast Wisconsin Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,851
per person
Oct 4 - Oct 9
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
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
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.
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.
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.
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.
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.
Ready to book your vacation to Southeast Wisconsin?
Southeast Wisconsin Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $186
CA $241 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,390 reviews)
"Great location."
Reviewed on Aug 26, 2026
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $111
CA $128 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (1,537 reviews)
"We had a glitch with our reservation but the staff, literally bent over backwards to help us solve the issue. We were so grateful! The rooms were very nice, and the location for restaurants, shopping, and frozen yogurt was great!"
Reviewed on Aug 27, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $205
CA $242 total
Sep 3 - Sep 4
includes taxes & fees
9.6/10 Exceptional! (2,231 reviews)
"Location and amenities are the best"
Reviewed on Aug 27, 2026
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.
Stay near popular Southeast Wisconsin attractions
Photo by Tim Ard
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.
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Southeast Wisconsin vacation package cost?
Much less than you might think — from as low as CA $1,338, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made vacation package, your getaway to Southeast Wisconsin is just clicks away.
How do I get a cheap travel package to Southeast Wisconsin?
Bundle your flights and hotels, add on extras such as activities, and save with a Southeast Wisconsin vacation package. You won't just pick up exciting discounts on your adventure — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 airlines and 1,000,000 hotels around the globe. Your next big adventure starts right here, right now!
Where should I stay in Southeast Wisconsin?
You'll fall in love with Milwaukee. Renowned sights, such as Milwaukee Art Museum and American Family Field, will keep you busy in this exciting city.
What are the top hotels in Southeast Wisconsin?
For hotels in Milwaukee with friendly service and comfy beds, you can't beat Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr. If you're visiting Lake Geneva as well, you can look forward to a solid night's sleep at Mt. Olympus Water & Theme Park Resort or Hilton Milwaukee City Center.
How far in advance should I book my Southeast Wisconsin vacation?
Savvy travelers always book early. Air carriers typically release flight tickets up to 12 months prior to departure, and this is your chance to land some of the lowest prices. Boss just told you to use up your vacation time next month? That's fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Southeast Wisconsin travel package include?
That's up to you. You can choose from a range of Southeast Wisconsin bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Southeast Wisconsin trip looks like, get set to save!
What should I know before booking a Southeast Wisconsin travel package?
When you book your hotels, flights and car rentals together, you'll land awesome discounts. Whether you're organizing a rural escape in a cottage or want to stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Southeast Wisconsin Expedia vacation package?
Definitely. Expedia has over 550 partner airlines to select from around the world. With so much choice, finding the right carrier to take you to Southeast Wisconsin will be a breeze.
If I'm not able to travel, can I cancel my Southeast Wisconsin vacation package?
It is possible to cancel your Southeast Wisconsin booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
