Southern Wisconsin Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Evae

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • 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.
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
Price was CA $1,429, price is now CA $1,057 per person
CA $1,057
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,318 reviews)
During off season not as many activities

Reviewed on Mar 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,924, price is now CA $1,236 per person
CA $1,236
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Clean room, very nice front desk and great location

Reviewed on Mar 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,651, price is now CA $1,087 per person
CA $1,087
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Would be nice if I had better view

Reviewed on Mar 25, 2026

Lodge Geneva National

Lodge Geneva National

4 out of 5
Price was CA $1,972, price is now CA $1,404 per person
CA $1,404
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,366 reviews)
It was ok rooms were noisy can here everything in hall and in next room

Reviewed on Mar 23, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,303, price is now CA $1,691 per person
CA $1,691
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Staff was soooo friendly

Reviewed on Mar 25, 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 skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

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

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Apr 9 to Apr 10
CA $261
CA $308 total
Apr 9 - Apr 10
includes taxes & fees
9.6/10 Exceptional! (2,035 reviews)
Amazing hotel - charm, food selection, nice swanky lounge at top of hotel

Reviewed on Mar 25, 2026

The Pfister Hotel
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 $163 per night from Apr 19 to Apr 20
CA $163
CA $188 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (3,576 reviews)
Very helpful front desk staff. We drove down. No airport shuttle was needed.

Reviewed on Mar 24, 2026

The Madison Concourse Hotel and Governor's Club
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Apr 12 to Apr 13
CA $164
CA $184 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Rooms are ok need some up dating and more options for guest.

Reviewed on Mar 23, 2026

Great Wolf Lodge Wisconsin Dells
See all 7,438 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

Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this 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

Bring the family to Kalahari Indoor Waterpark and have a fun-filled day at this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark

Frequently asked questions

Can I cancel my flight booking to Southern Wisconsin due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we recommend looking over the terms and conditions of your airfare before booking a seat.
What's the best way to find cheap flights to Southern Wisconsin that have flexible change policies?
By using our clever "No change fee" filter, that's how. All you have to do is enter your preferred dates and destination, click "Search," then click the checkbox directly under the "Flexible change policies" heading (it's on the left of your screen). Expedia makes it a snap to find inexpensive, flexible tickets to Southern Wisconsin.
What are some of the general tips for travelers to Southern Wisconsin during the COVID-19 outbreak?
In the face of the COVID-19 outbreak, traveling now comes with some extra challenges. Make a note of these valuable tips before jumping on your flight to Southern Wisconsin:
  • Understand what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight.
  • Wear a face mask during airport screening. A TSA employee will ask you to temporarily lower your mask for ID purposes.
  • Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. After that, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Southern Wisconsin?
Delta offers flights into or near Southern Wisconsin, including 573 that arrive at General Mitchell Intl. Airport (MKE) each month. Figure out your travel dates and then book your fare early for the best deal.
How can I find cheap tickets to Southern Wisconsin?
Book ahead of time, fly to or from nearby airports, avoid school vacation time — there are lots of ways! Another one is to take advantage of Expedia's "flexible dates" function. Search for your Southern Wisconsin flight, then check out the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to Southern Wisconsin was .
How much is a flight to Southern Wisconsin?
One-way flights leaving () sold for as low as in the last seven days. During this period, the cost of a round-trip journey to Southern Wisconsin ranged between and . If you find a fantastic deal, book fast — these prices don't wait around for long.
What are the most popular airports to fly into in Southern Wisconsin?
Get ready to pack your bags and fly into General Mitchell Intl. Airport (MKE), Southern Wisconsin's leading flight hub. Book one of the 2400 flights that touch down at this popular destination each month.
When is the cheapest time to fly to Southern Wisconsin?
Leave for Southern Wisconsin early on in the week and you'll usually be rewarded with cheaper fares. Tuesday is known for being the cheapest day to get on a plane, closely followed by Monday. If you're hoping to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Southern Wisconsin?
In the last seven days, airfares to Southern Wisconsin ranged between and . Prices depend on multiple things, particularly the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Southern Wisconsin employ COVID-19 cleanliness policies?
As lockdowns and restrictions start to lift, airlines are back in the skies with new strategies including physical distancing and an increased supply of face masks, gloves and sanitizer. Here's what some carriers are doing to help stop the spread of COVID-19:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.