Southern Wisconsin Holidays from AU$2,576

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Your Southern Wisconsin Holiday

Our Southern Wisconsin holiday 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 organising your Southern Wisconsin holiday. From hotels and flights, to car rentals and more, we know how to curate a travel experience like no other.

The Latest Southern Wisconsin Holiday 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 AU$5,156, price is now AU$2,576 per person
AU$2,576
per person
17 Oct - 24 Oct
just found
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Property has a very small load in space. Hotel key did not work on the room door twice. Swimming pool was out of order and it was buried in the fine print. Not what you want to find out on a hot sunny day. Other than that the property was clean and well maintained.

Reviewed on 1 Sep. 2025

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 AU$5,399, price is now AU$2,702 per person
AU$2,702
per person
17 Oct - 24 Oct
just found
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
Very nice views of Lake Michigan Beautiful room and bathroom Very pricey Staff at front deck was ok, I felt rushed and they weren’t very friendly.

Reviewed on 31 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$6,594, price is now AU$3,369 per person
AU$3,369
per person
17 Oct - 24 Oct
just found
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was AU$5,603, price is now AU$2,920 per person
AU$2,920
per person
17 Oct - 24 Oct
just found
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,971, price is now AU$2,606 per person
AU$2,606
per person
17 Oct - 24 Oct
just found
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back!

Reviewed on 31 Aug. 2025

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
Milwaukee

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

Southern Wisconsin Holiday

Southern Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Top Sights
Milwaukee County Zoo, Devils Lake State Park and Devils Lake

Our pick of the best 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 AU$77 per night from 3 Sept to 4 Sept
AU$77
3 Sept - 4 Sept
includes taxes & fees
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
Get rates
The Madison Concourse Hotel and Governor's Club
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 AU$333 per night from 21 Sept to 22 Sept
AU$333
21 Sept - 22 Sept
includes taxes & fees
The Pfister Hotel
See all 7,601 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Southern Wisconsin

University of Wisconsin-Madison

University of Wisconsin-Madison

Enjoy the student vibe around University of Wisconsin-Madison, a top university in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

Have a fun-filled day at Mt. Olympus Water and Theme Park and see why people love this theme park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Harley-Davidson Museum which includes 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.