$193 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 7/8. 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, 0 bags

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Everything you should know

Cheapest round-trip
$244
United Airlines
Fri 11/13Mon 11/16
ORD - LSE • Non-stop
Cheapest non-stop
$428
American Airlines
Wed 7/1Sun 7/12
ORD - LSE • Non-stop
Arrival airport
You can't fly directly to Winona. It is served by La Crosse (LSE), located 22.4 miles from Winona.
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Flight Deals
Useful Info
Flight Deals

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

Fri, Nov 13 - Mon, Nov 16
United Airlines Logo
4:45 pm - 6:10 pm
ORD
-
LSE
1h 25mnonstop
United Airlines Logo
8:15 pm - 9:39 pm
LSE
-
ORD
1h 24mnonstop
$244United Airlines
Sat, Jul 4 - Sat, Jul 18
American Airlines Logo
11:35 am - 6:13 pm
DCA
-
LSE
7h 38m
1 stop
American Airlines Logo
5:41 pm - 11:59 pm
LSE
-
DCA
5h 18m
1 stop
$270American Airlines
Sat, Jul 4 - Wed, Jul 15
American Airlines Logo
9:59 am - 6:13 pm
DCA
-
LSE
9h 14m
2 stops
American Airlines Logo
5:53 pm - 11:59 pm
LSE
-
DCA
5h 06m
1 stop
$276American Airlines
Sat, Nov 14 - Wed, Nov 18
United Airlines Logo
11:43 am - 1:05 pm
ORD
-
LSE
1h 22mnonstop
United Airlines Logo
9:42 am - 11:06 am
LSE
-
ORD
1h 24mnonstop
$299United Airlines
Tue, Jul 7 - Wed, Jul 15
American Airlines Logo
5:22 pm - 11:59 pm
DCA
-
LSE
7h 37m
1 stop
American Airlines Logo
5:53 pm - 11:59 pm
LSE
-
DCA
5h 06m
1 stop
$306American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
5:29 am - 11:54 am
EWR
-
LSE
7h 25m
1 stop
American Airlines Logo
3:14 pm - 11:59 pm
LSE
-
EWR
7h 45m
1 stop
$306American Airlines
Tue, Jul 7 - Wed, Jul 15
American Airlines Logo
5:00 am - 11:31 am
DCA
-
LSE
7h 31m
2 stops
American Airlines Logo
5:53 pm - 11:59 pm
LSE
-
DCA
5h 06m
1 stop
$312American Airlines
Wed, Dec 2 - Sat, Dec 5
United Airlines Logo
7:30 am - 8:56 am
ORD
-
LSE
1h 26mnonstop
United Airlines Logo
9:42 am - 11:06 am
LSE
-
ORD
1h 24mnonstop
$314United Airlines
Sat, Jul 4 - Wed, Jul 15
American Airlines Logo
9:59 am - 6:13 pm
DCA
-
LSE
9h 14m
2 stops
American Airlines Logo
12:01 pm - 9:26 pm
LSE
-
DCA
8h 25m
2 stops
$317American Airlines
Wed, Jul 1 - Sun, Jul 12
Multiple Airlines Logo
4:59 pm - 4:40 pm
ORD
-
LSE
23h 41m
1 stop
Multiple Airlines Logo
5:30 pm - 9:11 am
LSE
-
ORD
15h 41m
1 stop
$441Multiple Airlines
Useful Info

Good to know - Book Cheap Winona Plane Tickets

Low seasonApril
Cheapest flight$193
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 18% 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 Chicago O'Hare Intl Airport1h 21m
  • Which airlines fly to La Crosse?

    Many airlines fly to La Crosse, the most common ones being Delta, Sun Country Air, and American Airlines. See the amount of flights per week for popular airlines flying to La Crosse.

  • 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.
  • Looking for a cheap flight? 25% of our users found flights on this route for $56 or less one-way and $106 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winona flight deals.

Reviews of the top airlines 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.
7.3
Allegiant AirOverall score based on 694 reviews
8.1Crew
6.9Comfort
7.6Boarding
5.8Food
5.4Entertainment
Airline reviews

Seats were very uncomfortable and being charged for snacks and water.........

4.0 OkayDennis, May 2026
ICT - LAS
Read more Allegiant Air reviews

Seats were very uncomfortable and being charged for snacks and water.........

Allegiant actually impressed me, original inbound flight from PBG was so late they gave us a bird inbound from Des Moines and only left 1h late and gained 40 minutes back in the air. Comfortable flight with no frills but no complaints.

Flight was delayed. Crew was good but hot coffee was not available.

Great. No choice for n/a. No food or entertainment options

No food is available without purchasing it and there is no in-flight entertainment. Both of these are OK because we got an inexpensive flight from Allegiant and, otherwise, our experience was excellent.

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Everything you need to know for your flight to Winona