Southwest Wisconsin Vacation Packages

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Your Southwest Wisconsin Vacation

Choose a vacation 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 vacation to when you get back home, Expedia will take care of you every step of the way.

Top Southwest Wisconsin Vacation Deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
Great location and beautiful hotel with nice rooms and awesome rooftop!

Reviewed on Aug. 10, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service. Hotel is located right next to the river cruises. Walgreens is 3 minutes away by foot. Very safe neighborhood several excellent restaurants within 10 minutes on foot. Try Wildberry resta for breakfast excellent food. Sanda for Asian food and Grand Boucher French The pizza place next to hotel (bonjiourno) overrated and subpar

Reviewed on Aug. 12, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Overall the staff were very prompt and helpful. My only complaints with the hotel is the rooms are smaller than I expected, the 4 of us had a hard time fitting into a double bed room. It would have been nice to know that most of the food places around the hotel close on the weekend. Definitely not the best choice for a family. Proximity to activities were doable , but a little far. Wells street at night was a little scary over the weekend. Parking in Chicago is really crazy but I found parking for $18 a night on the same block without in and out access. We parked and left the car the whole time. Overall staff was amazing, nothing bad to say there, but I was disappointed as a first time visitor with the size of the hotel rooms, the cleanliness was fair, dark room, windows you couldn’t see out of well. The room temp was set at 65 but we were all swearing overnight and had to purchase a fan to help.

Reviewed on Aug. 13, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,829 reviews)
Helpful staff, beautiful hotel in a great location!

Reviewed on Aug. 12, 2025

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 a house, a park and flowers

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

Ready to book your vacation to Southwest Wisconsin?

 

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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 CA $55 per night from Sep 1 to Sep 2
CA $55
CA $62 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (2,341 reviews)
"All 10 of us adults and kids had such a great time. Every worker was so pleasant to be around. The Hotel Rome room was fantastic since I had 2 rooms and they adjoined each other. Price were pretty good for food and drinks. Had the rented table and umbrella - oh that was a big plus the extra money ..."

Reviewed on Aug. 12, 2025

Mt. Olympus Water & Theme Park Resort
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 CA $66 per night from Sep 1 to Sep 2
CA $66
CA $74 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,511 reviews)
"Friendly and accommodating staff, very clean"

Reviewed on Aug. 10, 2025

Days Inn & Suites by Wyndham Wisconsin Dells
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 CA $172 per night from Aug 31 to Sep 1
CA $172
CA $199 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (2,971 reviews)
"Check in folks were excellent and the bar was as well Rooms were clean Nd very reasonably priced"

Reviewed on Aug. 12, 2025

The Madison Concourse Hotel and Governor's Club
See all 3,789 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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Discover the most popular places to visit in Southwest Wisconsin

Mt. Olympus Water and Theme Park

Mt. Olympus Water and Theme Park

Enjoy the rides and games at Mt. Olympus Water and Theme Park and see why this is a favorite amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Mt. Olympus Water and Theme Park
Top Secret

Top Secret

Enjoy a stop at Top Secret, an entertaining place to visit in Wisconsin Dells. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Top Secret
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 waterparks in this family-friendly area.

Devil's Lake State Park

Frequently asked questions

How much does a Southwest Wisconsin vacation package cost?
Starting from an incredible CA $541, 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 vacation 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 travelers.
How far in advance should I book my Southwest Wisconsin vacation?
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 travelers 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 organizing a luxury city stay with your love or an affordable family break, check out our vacation packages today.
Can I choose my airline with a Southwest Wisconsin Expedia vacation package?
You can. We have more than 550 partner airlines globally, so go with the carrier that matches your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Wisconsin vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.