Search Cheap Flights to
Southwest Wisconsin

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Southwest Wisconsin Flights as Low as $229

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Wed, Jul 15 - Tue, Jul 28
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$229 Roundtrip, just found
$229
Roundtrip
just found
Select American Airlines flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Tue, Jul 28, priced at $229 just found
United
Wed, Jul 15 - Tue, Jul 28
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$244 Roundtrip, just found
$244
Roundtrip
just found
Select United flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Tue, Jul 28, priced at $244 just found
American Airlines
Thu, Jul 16 - Sun, Aug 2
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jul 16 from O'Hare Intl. to La Crosse Municipal, returning Sun, Aug 2, priced at $259 found 2 days ago
United
Wed, Jul 15 - Thu, Aug 6
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$260 Roundtrip, found 4 days ago
$260
Roundtrip
found 4 days ago
Select United flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Thu, Aug 6, priced at $260 found 4 days ago
United
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$260 Roundtrip, found 7 hours ago
$260
Roundtrip
found 7 hours ago
Select United flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $260 found 7 hours ago
United
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$270 Roundtrip, found 7 hours ago
$270
Roundtrip
found 7 hours ago
Select United flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $270 found 7 hours ago
United
Fri, Jul 17 - Wed, Aug 5
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select United flight, departing Fri, Jul 17 from O'Hare Intl. to La Crosse Municipal, returning Wed, Aug 5, priced at $275 found 4 days ago
American Airlines
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$280 Roundtrip, found 7 hours ago
$280
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $280 found 7 hours ago
United
Wed, Jul 15 - Thu, Aug 6
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$287 Roundtrip, found 4 days ago
$287
Roundtrip
found 4 days ago
Select United flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Thu, Aug 6, priced at $287 found 4 days ago
American Airlines
Wed, Jul 15 - Tue, Jul 28
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$299 Roundtrip, just found
$299
Roundtrip
just found
Select American Airlines flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Tue, Jul 28, priced at $299 just found
American Airlines
Wed, Jul 15 - Tue, Jul 28
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$305 Roundtrip, just found
$305
Roundtrip
just found
Select American Airlines flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Tue, Jul 28, priced at $305 just found
United
Wed, Jul 15 - Thu, Aug 6
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$305 Roundtrip, found 4 days ago
$305
Roundtrip
found 4 days ago
Select United flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Thu, Aug 6, priced at $305 found 4 days ago
United
Wed, Jul 15 - Tue, Jul 28
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$314 Roundtrip, just found
$314
Roundtrip
just found
Select United flight, departing Wed, Jul 15 from O'Hare Intl. to La Crosse Municipal, returning Tue, Jul 28, priced at $314 just found
American Airlines
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$316 Roundtrip, found 7 hours ago
$316
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $316 found 7 hours ago
American Airlines
Mon, Jul 20 - Fri, Jul 31
ORD
O'Hare Intl.
LSE
La Crosse Municipal
$320 Roundtrip, found 21 hours ago
$320
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Mon, Jul 20 from O'Hare Intl. to La Crosse Municipal, returning Fri, Jul 31, priced at $320 found 21 hours ago
Delta
Wed, May 13 - Sun, May 24
ORD
O'Hare Intl.
MSN
Dane County Regional
$670 Roundtrip, found 7 hours ago
$670
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, May 13 from O'Hare Intl. to Dane County Regional, returning Sun, May 24, priced at $670 found 7 hours ago

Cheap Flights to Southwest Wisconsin

Fall in love at first flight with your vacation to Southwest Wisconsin by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Southwest Wisconsin on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Southwest Wisconsin, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Southwest Wisconsin

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Southwest Wisconsin with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the RFD airport.

What is the cheapest month to fly to Southwest Wisconsin?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Southwest Wisconsin are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Southwest Wisconsin?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Southwest Wisconsin.

What airport is best to fly into Southwest Wisconsin?

When you’re planning your trip to Southwest Wisconsin, convenience is the name of the game. Luckily, Southwest Wisconsin Dane County Regional Airport is nearby so you can deplane and get going on checking off everything on your Southwest Wisconsin must-do list.

How much are flights to Southwest Wisconsin?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Southwest Wisconsin on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $229, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Southwest Wisconsin?

The trick to saving a stack of cash on your flight to Southwest Wisconsin? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $229 right now, why wait?

Southwest Wisconsin Flight Information
Destination airport
La Crosse Municipal
Destination airport IATA code
LSE
Roundtrip price
$228

Last Minute Hotel Deals in Southwest Wisconsin

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
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (3,681 reviews)
Excellent!

Reviewed on Apr 27, 2026

Get rates
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
Book a stay at this family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise the ...
Get rates
Mt. Olympus Water & Theme Park Resort
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Book a stay at this family-friendly resort in Baraboo. Enjoy 6 indoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,006 reviews)
We have a 2 year old and a 15 year old. Both had a great time. Clean rooms.

Reviewed on Apr 26, 2026

Get rates
Great Wolf Lodge Wisconsin Dells
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,009 reviews)
Nice hotel. Good food. We did not use the pool or gym.

Reviewed on Apr 27, 2026

Get rates
DoubleTree by Hilton Madison East
Natura Treescape Resort

Natura Treescape Resort

2.5 out of 5
400 County Road A Wisconsin Dells WI
Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, 2 indoor pools, and a private beach. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (1,131 reviews)
maybe teach staff to be nicer and speak clear so customers can understand

Reviewed on Apr 23, 2026

Get rates
Natura Treescape Resort
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
Great hotel

Reviewed on Apr 21, 2026

Get rates
Best Western Plus InnTowner Madison
Natura Vue Resort & Boathouse

Natura Vue Resort & Boathouse

2.5 out of 5
1015 River Rd Wisconsin Dells WI
Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, an outdoor pool, and a marina. Our guests praise the restaurant and the helpful staff in ...
8.2/10 Very Good! (1,251 reviews)
There was a small issue with check in

Reviewed on Apr 24, 2026

Get rates
Natura Vue Resort & Boathouse
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
Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,732 reviews)
Parking close and easy. Upgrading was well worth it for extra room.

Reviewed on Apr 26, 2026

Get rates
Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,755 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.

Top Hotels With Free Airport Shuttle

Best Western East Towne Suites

Best Western East Towne Suites

2.5 out of 5
4801 Annamark Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,002 reviews)
Parts of the hotel have fresh paint and carpet, but most of it needs a lot of TLC. It's poorly maintained. The breakfast room was dirty. They only had 1 person there to clean, refill and maintain the room. He was not able to keep up. They should have more help. It was gross. The staff were friendly ...

Reviewed on Apr 27, 2026

Get rates
Best Western East Towne Suites
AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

2.5 out of 5
1835 Rose Street La Crosse WI
Book a stay at this beach hotel in La Crosse. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
7.6/10 Good! (1,001 reviews)
Would stay again.

Reviewed on Apr 25, 2026

Get rates
AmericInn by Wyndham La Crosse Riverfront-Conference Center
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
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
8/10 Very Good! (1,234 reviews)
The room was not clean. Dusty and one of the pillows looked like it wasn’t even washed. The sink drain was extremely slow, pool didn’t have any clean tools. Hotel staff clearly didn’t want to be at work. Breakfast was average.

Reviewed on Apr 26, 2026

Get rates
Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
Great hotel

Reviewed on Apr 21, 2026

Get rates
Best Western Plus InnTowner Madison
Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
22 S Carroll Street Madison WI
Book a stay at this spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,003 reviews)
Excellent location-walk to all the places downtown. Bed was comfortable!

Reviewed on Apr 24, 2026

Get rates
Best Western Premier Park Hotel
AmericInn by Wyndham Prairie du Chien

AmericInn by Wyndham Prairie du Chien

2 out of 5
37502 Us Highway 35 And 18 S Prairie Du Chien WI
Book a stay at this business-friendly hotel in Prairie Du Chien. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (606 reviews)
Clean rooms, good continental breakfast, and friendly staff. Very reasonably placed hotel

Reviewed on Apr 26, 2026

Get rates
AmericInn by Wyndham Prairie du Chien
See all 3,755 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.