Southern Wisconsin Vacation Packages
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Your Southern Wisconsin Vacation
Our Southern Wisconsin vacation packages provide an easy, affordable and immersive way to experience everything this incredible destination has to offer. If it's distilleries and craft breweries and dining you're after, this is the place to be. With so much to see and do on a trip to Southern Wisconsin, it can be hard 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 city worthy of a spot on your itinerary is Wisconsin Dells. Be sure not to miss Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Expedia is a one-stop shop when it comes to organizing your Southern Wisconsin vacation. From hotels and flights, to car rentals and more, we know how to curate a travel experience like no other.
Top Southern Wisconsin Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
CA $1,062
per person
Oct 2 - Oct 6
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
Front desk staff were very friendly and helpful even though we didn't get to the hotel until after midnight because of flight delays.
Reviewed on Aug 10, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,405
per person
Oct 2 - Oct 6
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel is in a great spot! We loved everything about our stay except the fact the lobby bar closes at 11 on a Saturday night! 8.5/10
Reviewed on Aug 10, 2026
Where to stay in Southern Wisconsin
Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern 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.
Downtown Madison
The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.
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.
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.
Lake Delton
1 out of top 10 points of interest in this area
If you're spending some time in Lake Delton, Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are top sights worth seeing.
Ready to book your vacation to Southern Wisconsin?
Southern Wisconsin Hotel Deals
Mt. Olympus Water & Theme Park Resort
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
CA $70
CA $78 total
Aug 30 - Aug 31
includes taxes & fees
7/10 Good! (2,895 reviews)
"Cool"
Reviewed on Aug 10, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $187
CA $243 total
Sep 7 - Sep 8
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
CA $168
CA $194 total
Sep 6 - Sep 7
includes taxes & fees
9.4/10 Exceptional! (4,082 reviews)
"Without a doubt the best hotel fitness room I’ve ever seen. Downsides would be the very small rooms. We had to switch rooms for the last night, and both rooms were not much bigger than the undersized queen beds. Claustrophobic! Make sure you have a small car if you plan on parking onsite, as it’s ..."
Reviewed on Aug 10, 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 Southern 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.
Mt. Olympus Water and Theme Park
7.4/10 (1,284 reviews)
Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
Photo by Noelani Irene Herner
EAA Aviation Museum
9.2/10 (245 reviews)
You can spend an afternoon studying the exhibits at EAA Aviation Museum in Oshkosh. Visit the area's shops or attend a sporting event.
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.
Camp Randall Stadium
9.0/10 (1,067 reviews)
Catch an event at Camp Randall Stadium during your trip to Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Kalahari Indoor Waterpark
8.8/10 (445 reviews)
Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.
Noah's Ark Waterpark
8.4/10 (959 reviews)
Enjoy the excitement at Noah's Ark Waterpark and find out why this is a popular amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
Chula Vista Waterparks
7.6/10 (630 reviews)
Enjoy a stop at Chula Vista Waterparks, an entertaining place to visit in Wisconsin Dells. While you're in the area, stroll along the riverfront.
Frequently asked questions
How much does a Southern Wisconsin vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Southern Wisconsin from just CA $1,062. And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Southern Wisconsin?
Our Southern Wisconsin vacation packages promise plenty of savings for the savvy traveler. For the best deal, simply bundle your flights, hotels and activities into one neat package. But great bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels throughout the world to choose from. Whatever your style, there's a vacation package with your name on it.
Where should I stay in Southern Wisconsin?
What are the top hotels in Southern Wisconsin?
When it comes to hotels in Milwaukee, Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr are among the favorites. If you're also staying in Wisconsin Dells, Inn of the Pines and Silver Spruce Resort are waiting to welcome you.
How far in advance should I book my Southern Wisconsin vacation?
Savvy travelers often book early. You can usually start comparing international fares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Cheap prices sometimes occur just weeks before departure.
What does an Expedia Southern Wisconsin travel package include?
From hotels and flights to car rentals, Expedia can help you put together a Southern Wisconsin package that works for you. Heading away for a few weeks? Check out a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, a flight and hotel deal could be more your style. Tours and activities can be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Southern Wisconsin travel package?
So many places to travel to, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and see how much you save.
If I'm not able to travel, can I cancel my Southern Wisconsin vacation package?
Yes, you can cancel your Southern Wisconsin booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out 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.
