Southwest Wisconsin Holidays from AU$574

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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.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was AU$679, price is now AU$574 per person
AU$574
per person
22 Jan - 25 Jan
found 23 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
9/10 Wonderful! (3,188 reviews)

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was AU$839, price is now AU$675 per person
AU$675
per person
22 Jan - 25 Jan
found 23 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
8.8/10 Excellent! (1,390 reviews)

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was AU$731, price is now AU$591 per person
AU$591
per person
22 Jan - 25 Jan
found 23 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
9.4/10 Exceptional! (1,106 reviews)
Had a great time and the place had a great breakfast and staff!

Reviewed on 30 Oct 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was AU$753, price is now AU$628 per person
AU$628
per person
22 Jan - 25 Jan
found 23 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
8.6/10 Excellent! (2,885 reviews)

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was AU$705, price is now AU$604 per person
AU$604
per person
22 Jan - 25 Jan
found 23 hours ago
Return flight included
Los Angeles (QLA) to Chicago (ORD)
7.6/10 Good! (1,864 reviews)

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
A large domed building surrounded by modern cityscape and a body of water.

Downtown Madison

2 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

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

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 AU$194 per night from 8 Nov to 9 Nov
AU$194
8 Nov - 9 Nov
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Natura Vue Resort & Boathouse

Natura Vue Resort & Boathouse

2.5 out of 5
1015 River Rd Wisconsin Dells WI
The price is AU$124 per night from 1 Dec to 2 Dec
AU$124
1 Dec - 2 Dec
includes taxes & fees
8.4/10 Very good! (1,279 reviews)
"Great staff but very old decor and rooms are outdated deary restaurant not open until 4"

Reviewed on 28 Oct 2026

Natura Vue Resort & Boathouse
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundable
The price is AU$72 per night from 1 Dec to 2 Dec
AU$72
1 Dec - 2 Dec
includes taxes & fees
6.2/10 (1,059 reviews)
"They sold my room after I had booked it with Expedia and had my confirmation number. And when I called the staff was very rude and disrespectful"

Reviewed on 28 Oct 2026

Motel 6 Madison, WI - East
See all 3,935 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Southwest Wisconsin attractions

A coastal landscape with autumn foliage, a beach, and a building.

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.
See properties

Frequently asked questions

How much does a Southwest Wisconsin holiday package cost?
Starting from an incredible AU$574, you can handcraft your own Southwest Wisconsin package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Southwest Wisconsin?
If you love scoring a bargain, bundle your bookings into a Southwest Wisconsin holiday package. Whether you're looking for hotels, flights, activities or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1 000 000 hotel options globally to pick from. Fly with who you prefer, book a room where you like and save a tidy sum — now that's the ideal escape!
What are the top hotels in Southwest Wisconsin?
Chula Vista Resort, Trademark Collection by Wyndham and Adams Inn know how to make their guests feel at home in Wisconsin Dells. If your travel plans also include Baraboo, check out La Quinta Inn & Ste by Wyndham Wisconsin Dells- Lake Delton and Days Inn & Suites by Wyndham Wisconsin Dells. Both are popular with travellers.
How far in advance should I book my Southwest Wisconsin holiday?
It all depends on the airline, but you can usually look up international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travellers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Southwest Wisconsin travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Southwest Wisconsin getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Southwest Wisconsin travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything together will make your trip planning easier. So why waste your time or money? Whether you're organising a luxury city stay with your love or an affordable family break, check out our holiday packages today.
Can I choose my airline with a Southwest Wisconsin Expedia holiday package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and travelling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin holiday package?
Yes, it's possible to cancel your Southwest Wisconsin booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

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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.