Southern Wisconsin Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,073, price is now CA $658 per person
CA $658
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on Aug. 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,441, price is now CA $1,974 per person
CA $1,974
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,444, price is now CA $1,439 per person
CA $1,439
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on Aug. 17, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,954, price is now CA $2,330 per person
CA $2,330
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was CA $1,046, price is now CA $662 per person
CA $662
per person
Oct 11 - Oct 14
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on Aug. 18, 2025

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
Milwaukee

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.

Find hotels in Downtown Milwaukee

Ready to book your vacation to Southern Wisconsin?

 

Choose your dates

Southern Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is CA $62 per night from Sep 1 to Sep 2
CA $62
CA $70 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (2,351 reviews)
"Great"

Reviewed on Aug. 18, 2025

Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Aug 31 to Sep 1
CA $174
CA $200 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (2,997 reviews)
"good"

Reviewed on Aug. 18, 2025

The Madison Concourse Hotel and Governor's Club
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Sep 2 to Sep 3
CA $184
CA $237 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,222 reviews)
I give this hotel a 10/10
"Very nice view of water. Friendliest staff ever. The housekeepers were always smiling. Very clean. Amenities were plentiful. Very comfortable room."

Reviewed on Aug. 18, 2025

Harbor Shores on Lake Geneva
See all 7,460 properties in Southern 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Southern Wisconsin

Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

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.

Mt. Olympus Water and Theme Park
Harley-Davidson Museum featuring interior views

Harley-Davidson Museum

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.

Harley-Davidson Museum

Kalahari Indoor Waterpark

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.

Kalahari Indoor Waterpark

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 $658. 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?
To see popular sights like Milwaukee Art Museum and American Family Field, Milwaukee is the place to be. Lots of travelers also love visiting Appleton, home to Gardens of the Fox Cities and Hearthstone Historic House Museum. If time is on your side, why not visit both cities?
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.