$345 Find Cheap Flights to Winona

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Winona departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights to Winona

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Winona that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Winona

Thu, Nov 27 - Sat, Nov 29
American Airlines Logo
8:00 am - 9:20 amORD-LSE
1h 20mnonstop
American Airlines Logo
9:50 am - 11:11 amLSE-ORD
1h 21mnonstop
$367American Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
4:31 pm - 5:45 pmORD-LSE
1h 14mnonstop
American Airlines Logo
4:10 pm - 5:34 pmLSE-ORD
1h 24mnonstop
$405American Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
American Airlines Logo
4:31 pm - 5:45 pmORD-LSE
1h 14mnonstop
American Airlines Logo
6:00 am - 7:24 amLSE-ORD
1h 24mnonstop
$445American Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1
American Airlines Logo
7:10 am - 5:58 pmBOS-LSE
11h 48m2 stops
American Airlines Logo
10:54 am - 4:49 pmLSE-BOS
4h 55m1 stop
$452American Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1
American Airlines Logo
11:05 am - 5:58 pmBOS-LSE
7h 53m2 stops
American Airlines Logo
10:54 am - 7:11 pmLSE-BOS
7h 17m2 stops
$457American Airlines
Find Deal
Wed, Oct 29 - Sat, Nov 1
American Airlines Logo
12:41 pm - 5:58 pmBOS-LSE
6h 17m1 stop
American Airlines Logo
6:15 pm - 11:54 pmLSE-BOS
4h 39m1 stop
$458American Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
American Airlines Logo
5:24 am - 10:24 amBOS-LSE
6h 00m1 stop
American Airlines Logo
6:00 am - 11:33 amLSE-BOS
4h 33m1 stop
$470American Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
9:25 am - 5:45 pmDEN-LSE
7h 20m1 stop
American Airlines Logo
4:10 pm - 10:22 pmLSE-DEN
7h 12m1 stop
$476American Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
American Airlines Logo
11:00 am - 5:45 pmBOS-LSE
7h 45m2 stops
American Airlines Logo
9:50 am - 6:29 pmLSE-BOS
7h 39m1 stop
$476American Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
American Airlines Logo
12:20 pm - 5:45 pmBOS-LSE
6h 25m2 stops
American Airlines Logo
9:50 am - 6:47 pmLSE-BOS
7h 57m2 stops
$481American Airlines
Find Deal

Everything you should know

Cheapest round-trip
$367
American Airlines
Thu 11/27Sat 11/29
ORD - LSE • Non-stop
Cheapest one-way
$345
American Airlines
Tue 12/16
ORD - LSE • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winona!
Useful Info

Good to know - Book Cheap Winona Plane Tickets

Low seasonMarch
Cheapest flight$345
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to La Crosse

FAQs - booking Winona flights

  • How long is the flight to Winona?

    Flights from Chicago1h 21m

  • How to fly to Winona?

    You cannot fly directly to Winona. KAYAK recommends you fly to La Crosse (LSE) (22.4 miles from Winona). From there you can rent a car or get a taxi.

  • What airports are near Winona?

    The closest airport is La Crosse (LSE) (22.4 mi). Other nearby airports are Rochester (RST) (43.66 mi), Sparta/Fort McCoy (CMY) (45.21 mi), Eau Claire (EAU) (56.8 mi) or Minneapolis St Paul (MSP) (96.33 mi). KAYAK recommends you fly to La Crosse.

  • How far is La Crosse Airport from central La Crosse?

    The city center of La Crosse is 5 miles from La Crosse Airport.

  • What is the name of La Crosse’s airport?

    There is only 1 airport in La Crosse, called La Crosse Airport (LSE). It can also be referred to as La Crosse or La Crosse Mnpl.

  • How does KAYAK find such low prices on flights to Winona?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Winona.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Winona?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winona is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Winona?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winona with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Winona?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winona up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Winona

  • There is no major airport in Winona. It is instead served by La Crosse Airport.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winona flight deals.

Reviews of the top airline flying to Winona

 
Need help choosing which airline to fly with from the United States to Winona? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11026 reviews
6.9Entertainment
6.4Food
7.5Boarding
7.2Comfort
8.0Crew
Airline reviews

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

8.0 ExcellentChristina, Oct 2025BTV - CLT
Read more American Airlines reviews

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Everything you need to know for your flight to Winona

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