Southwest Wisconsin Holidays from AU$1,858

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Your Southwest Wisconsin Holiday

Southwest Wisconsin's rich history and spectacular views are just the start of the great things this destination offers. Make the most of your break by building your own Southwest Wisconsin holiday package. The best and easiest way to organise your trip to Southwest Wisconsin is to start with its most popular cities, which include Wisconsin Dells, La Crosse and Lake Delton. Start packing your bags, because your Southwest Wisconsin holiday is only a few clicks away with Expedia.

The Latest Southwest Wisconsin Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
7.8/10 Good! (8,267 reviews)
I love the character of old hotels and this one did not disappoint. Pros: we had hot water for showers, plenty of towels, a comfortable bed, two onsite restaurants to choose from, and two complimentary bottles of water in our room. We called for room service one night; they were friendly and fast. The food was excellent and the portion sizes were more than generous. I ordered the hummus and the tacos, both appetizers, and I had enough food to feed 4 people! My husband ordered the club sandwich and he, too, could have fed 4 people with the size sandwich and amount fries he got. Cons: the temperature could not be set. It was either heat or nothing. Spend the extra money if you want a room with a view or you’ll be disappointed looking out your window. We would definitely recommend this hotel.

Reviewed on 25 Dec. 2024

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,923 reviews)
Amazing view of the river and the city, well worth the money and will definitely be coming back. Rooms are clean and staff is very helpfully and nice.

Reviewed on 27 Dec. 2024

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,197 reviews)
I was really happy during my stay here at RIU. Everything was perfect! Staff, atmosphere, vibe, the breakfast buffet- all amazingly good. Loved my room very much. had a little view of Michigan ave since they gave me the higher floor. it was just a nice overnight stay...will be back for sure❤️

Reviewed on 27 Dec. 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,246 reviews)
Room was marvelous. But water leaking into a bucket in hallway. No hot water! Had to take COLD shower in VIP suite

Reviewed on 23 Dec. 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,458 reviews)
Everything was perfect

Reviewed on 26 Dec. 2024

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 featuring flowers, a house and a garden

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 hotel + flight trips 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$257 per night from 5 Jan to 6 Jan
AU$257
includes taxes & fees
5 Jan - 6 Jan 2025
9.4/10 Exceptional! (2,197 reviews)
"Always an amazing stay! We stay on the Club level to enjoy the Governors Club. It never disappoints with the atmosphere in the lounge! I will say that the rooms could use some updating to match the vibe given off by the rest of the hotel. Freshen the decor up a bit."

Reviewed on 26 Dec. 2024

The Madison Concourse Hotel and Governor's Club
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$119 per night from 5 Jan to 6 Jan
AU$119
includes taxes & fees
5 Jan - 6 Jan 2025
6.6/10 (1,906 reviews)
"If you go in the winter only book a room at Hotel Rome. That’s connected to the indoor water park and theme park… You will have to walk outside for a quick second to get the the Theme Park… The water park we didn’t have to go outside at all to get to it… It was very close."

Reviewed on 25 Dec. 2024

Mt. Olympus Water & Theme Park Resort
DoubleTree by Hilton Madison East
DoubleTree by Hilton Madison East
4 out of 5
4402 E Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 2 Jan to 3 Jan
AU$203
includes taxes & fees
2 Jan - 3 Jan 2025
9.2/10 Wonderful! (824 reviews)
"On the road way, yet still quiet quiet and close to interstate"

Reviewed on 15 Dec. 2024

DoubleTree by Hilton Madison East
See all 3,585 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

Frequently asked questions

How much does a Southwest Wisconsin holiday package cost?
Starting from an incredible AU$1,858, 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.

Discover the most popular places to visit in Southwest Wisconsin

Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

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 riverfront or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Devil's Lake State Park

Devil's Lake State Park

Explore the great outdoors at Devil's Lake State Park, a lovely green space in Wisconsin Dells. Stroll along the lakeside or visit the fun-filled water parks in this family-friendly area.

Devil's Lake State Park

Noah's Ark Waterpark

Bring the family to Noah's Ark Waterpark and have a fun-filled day at this theme park in Lake Delton. Stroll along the area's riverfront or experience its entertainment choices.

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