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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location

Reviewed on Jun 24, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 19 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.

Reviewed on Jun 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,891, price is now CA $1,359 per person
CA $1,359
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

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

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 $149 per night from Jul 16 to Jul 17
CA $149
CA $167 total
Jul 16 - Jul 17
includes taxes & fees
7/10 Good! (2,838 reviews)
"Very disappointed in the stay in Wisconsin Dells. Our room looks nothing like the pictures, the shower leaks all over the bathroom and today we asked to have our sheets changed due to our son peeing in the bed and they just left sheets on the bed for us to change it with no blankets at all. I would ..."

Reviewed on Jun 26, 2026

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
The price is CA $168 per night from Jun 28 to Jun 29
CA $168
CA $194 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (3,894 reviews)
"Second time in ten days we chose to stay and again it was the right choice all around!"

Reviewed on Jun 26, 2026

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Jun 29 to Jun 30
CA $96
CA $111 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (1,327 reviews)
"Very clean"

Reviewed on Jun 25, 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 3,756 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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Stay near popular Southwest Wisconsin attractions

Slidewheel water at a water park.

Mt. Olympus Water and Theme Park

7.4/5 (1,284 reviews)
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 lakeside or experience its entertainment choices.
See properties

Frequently asked questions

Can I cancel my flight booking to Southwest Wisconsin due to COVID-19?
Our Customer Service Portal is where you can get important information about changing or canceling your flight due to COVID-19. Before you reserve a seat, it's a good idea to look over the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Southwest Wisconsin that have flexible change policies?
It's as easy as counting to three with Expedia. First, enter your preferred travel dates and press "Search." Step 2: Check the "No change fee" box below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Reserve your flexible and cheap ticket to Southwest Wisconsin.
What are some of the general tips for travelers to Southwest Wisconsin during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a bit different these days. These are some helpful things to know before you hop on that plane to Southwest Wisconsin:
  • Investigate if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any requirements you'll need to follow on arrival, such as taking a COVID-19 test.
  • When you pass through airport screening, do not remove your face mask. You will be asked to lower it briefly for identification purposes. Travelers who refuse to wear a mask may face civil penalties and may also be escorted from the terminal.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. Once that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for scanning.
  • To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on instead of into the bins.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Southwest Wisconsin?
Arrange your airfare with United Airlines and then start piecing together your Southwest Wisconsin to-do list. This leading airline provides 238 flights every month to Dane County Regional Airport (MSN), a major gateway.
How can I find cheap tickets to Southwest Wisconsin?
In the last seven days, was the best price for a flight to Southwest Wisconsin. If you want to save even more, book ahead of time and be flexible with your travel dates. Search for your flight to Southwest Wisconsin, then see prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Southwest Wisconsin?
The cost of a round-trip flight to Southwest Wisconsin in the last seven days fluctuated between and . If you were heading one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Wisconsin?
Jet into Dane County Regional Airport (MSN) and enjoy all that Southwest Wisconsin has to offer. As the region's main entry point, around 1068 flights touch down here each month.
When is the cheapest time to fly to Southwest Wisconsin?
If you can be flexible with what date you travel to Southwest Wisconsin, try to fly out earlier in the week. The most economical day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with many vacationers opting to take off on the weekend.
How much is a plane ticket to Southwest Wisconsin?
In the last seven days, fares varied between and . Have a look at our fantastic deals to Southwest Wisconsin, pick your favorite and then start packing your bags.
Which airlines with flights to Southwest Wisconsin employ COVID-19 cleanliness policies?
In response to the current pandemic, many airlines have adopted extra rules and standards to help their passengers fly with peace of mind. Check out what these carriers are doing:
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.