Southwest Wisconsin Holidays from AU$2,184

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Your Southwest Wisconsin Holiday

Choose a holiday package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. La Crosse is another favourite city with Southwest Wisconsin travellers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Centre. From the moment you book your Southwest Wisconsin holiday to when you get back home, Expedia will take care of you every step of the way.

The Latest Southwest 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$3,172, price is now AU$2,184 per person
AU$2,184
per person
20 Oct - 26 Oct
found 22 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on 29 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 19 hours ago
Return direct 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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 19 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 22 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 22 hours ago
Return flight included
Melbourne (MEL) 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

Our guide on where to stay in Southwest Wisconsin

Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
Madison which includes flowers, a house and a park

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.

Find hotels in Downtown Madison

Southwest Wisconsin Holiday

Southwest Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Top Sights
Devils Lake State Park, Devils Lake and Mirror Lake State Park

Our pick of the best Southwest 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
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is AU$83 per night from 30 Sept to 1 Oct
AU$83
30 Sept - 1 Oct
includes taxes & fees
Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,791 properties in Southwest 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.
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beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Southwest 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

Kalahari Indoor Waterpark

Enjoy the rides and games at Kalahari Indoor Waterpark and see why this is a favourite theme park in Baraboo. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

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