Southern Wisconsin Holidays from NZ$991

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The Latest Southern Wisconsin Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

NZ$991
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
7.8/10 Good! (2,004 reviews)
N

Reviewed on 19 Sept 2026

Regal Inn - Chicago O'Hare Airport

Regal Inn - Chicago O'Hare Airport

NZ$1,026
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
8/10 Very good! (1,001 reviews)
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

NZ$1,023
per person
24 Nov - 29 Nov
found 1 day ago
Return direct flight included
Pittsburgh (PIT) to Chicago (ORD)
7.2/10 Good! (1,542 reviews)

Our guide on 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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee
A large domed building surrounded by modern cityscape and a body of water.

Downtown Madison

1 out of top 10 points of interest in this area

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Overture Center for the Arts or Orpheum Theater might round out your trip.

Find hotels in Downtown Madison
A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

Travellers come to Wauwatosa for its abundant dining options, and you can see top attractions like Mayfair Mall and The Mayfair Collection while you're in town.

Find hotels in Wauwatosa
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.

Find hotels in West Allis
A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience Milwaukee’s hot spot for art and fashion when you check out the dynamic boutiques, restaurants, theaters and galleries that fill this exciting district.

Find hotels in Historic Third Ward

Southern Wisconsin Holiday

Our pick of the best Southern Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
NZ$103
20 Sept - 21 Sept
includes taxes & fees
Mt. Olympus Water & Theme Park Resort
The Pfister Hotel

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI
NZ$401
20 Sept - 21 Sept
includes taxes & fees
The Pfister Hotel
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
NZ$238
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (4,177 reviews)
"Stay here amazing experience. I was in town for Ironman Wisconsin and walked everywhere! Great pool, hot tub and sauna in hotel. Food was amazing and super good room service, Starbucks added my coffee fix. Great stay in Madison walkable to great night life, dining, concerts/shows, and to Monona terrace. ..."

Reviewed on 19 Sept 2026

The Madison Concourse Hotel and Governor's Club
See all 7,754 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.

Stay near popular Southern 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.
See properties
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 water park with a large Ferris wheel and a water slide.

Mt. Olympus Water and Theme Park

7.4/10 (1,284 reviews)
Bring the family to Mt. Olympus Water and Theme Park and have a fun-filled day at this theme park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.
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Kalahari Indoor Waterpark

8.8/10 (445 reviews)
Enjoy the rides and games at Kalahari Indoor Waterpark and see why this is a favourite theme park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.
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Noah's Ark Waterpark

8.4/10 (959 reviews)
Bring the family to Noah's Ark Waterpark and have a fun-filled day at this theme park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.
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The House on the Rock

9.4/10 (246 reviews)
You can find out about the history of Spring Green with a stop at The House on the Rock. You can enjoy the cafes while in the area.
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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.
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Frequently asked questions

How much does a Southern Wisconsin holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Southern Wisconsin from just NZ$991. 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 holiday packages promise plenty of savings for the savvy traveller. 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 holiday 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 travellers 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 favourites. 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 holiday?
Savvy travellers 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 holiday 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.