$29 Find Cheap Flights to Winter Park

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Winter Park departing on 3/19. 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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Cheap Flights to Winter Park

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Winter Park 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 Winter Park

Thu, Mar 26 - Mon, Mar 30
Frontier Logo
5:45 am - 7:02 am
DFW
-
DEN
2h 17mnonstop
Frontier Logo
9:00 pm - 12:06 am
DEN
-
DFW
2h 06mnonstop
$58Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
10:34 pm - 11:58 pm
DFW
-
DEN
2h 24mnonstop
Frontier Logo
5:15 pm - 8:29 pm
DEN
-
DFW
2h 14mnonstop
$59Frontier
Tue, Apr 7 - Thu, Apr 16
Southwest Logo
5:45 pm - 7:25 pm
HOU
-
DEN
2h 40mnonstop
Southwest Logo
8:55 pm - 12:25 am
DEN
-
HOU
2h 30mnonstop
$144Southwest
Fri, Apr 10 - Mon, Apr 13
Southwest Logo
6:05 am - 7:35 am
HOU
-
DEN
2h 30mnonstop
Southwest Logo
7:20 am - 10:50 am
DEN
-
HOU
2h 30mnonstop
$145Southwest
Fri, Apr 10 - Sat, Apr 11
American Airlines Logo
6:01 am - 9:37 am
HOU
-
DEN
4h 36m
1 stop
American Airlines Logo
5:14 pm - 11:47 pm
DEN
-
HOU
5h 33m
1 stop
$165American Airlines
Tue, Mar 17 - Tue, Mar 24
American Airlines Logo
6:30 am - 11:53 am
JFK
-
DEN
7h 23m
1 stop
American Airlines Logo
11:59 pm - 10:14 am
DEN
-
JFK
8h 15m
1 stop
$167American Airlines
Fri, May 1 - Tue, May 5
United Airlines Logo
4:59 pm - 7:40 pm
LGA
-
DEN
4h 41mnonstop
United Airlines Logo
5:31 pm - 11:24 pm
DEN
-
LGA
3h 53mnonstop
$171United Airlines
Tue, Mar 31 - Sat, Apr 4
Delta Logo
7:10 pm - 9:46 pm
JFK
-
DEN
4h 36mnonstop
Delta Logo
11:59 pm - 6:00 am
DEN
-
JFK
4h 01mnonstop
$172Delta
Wed, May 6 - Sat, May 9
Delta Logo
6:59 am - 12:04 pm
LGA
-
DEN
7h 05m
1 stop
Delta Logo
1:20 pm - 11:44 pm
DEN
-
LGA
8h 24m
1 stop
$177Delta
Sat, May 30 - Tue, Jun 2
United Airlines Logo
4:57 pm - 7:45 pm
BOS
-
DEN
4h 48mnonstop
United Airlines Logo
11:59 pm - 5:58 am
DEN
-
BOS
3h 59mnonstop
$205United Airlines
Useful Info

Good to know - Book Cheap Winter Park Plane Tickets

Low seasonJanuary
Cheapest flight$29
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Dallas/Fort Worth Airport to Denver

Flights to Winter Park: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Winter Park 
DebraFlew with Alaska Airlines
SEA
-
DEN
Feb 2026
Seattle TSA much improved. Faster service. Baggage check-in ok. I'm sure will get faster as people get used to it.
MeghanFlew with Southwest
MCO
-
DEN
Feb 2026
MCO security doesn't have a mobile liquid container to drain your water bottles between the ID check and the luggage scan, you have to empty your bottles before you get in line (or drink it all before you make it to the luggage scan). Many other airports offer a space to empty your drink out, or warn you of that ahead of time, for MCO the warning didn't display until after you get through the ID check which was not helpful as there's no way to exit to find a sink once you're past that point.
Verified travelerFlew with Frontier
PDX
-
DEN
Jun 2025
Make sure your carry on bag meets the size limit as bin space on plane is limited. Check any bags online in advance to avoid extra charges for using agent at the airport.
Verified travelerFlew with Frontier
GRR
-
DEN
Jun 2025
Don't purchase vouchers with connections on the cheaper flights (such as frontier or Spirit), you're bound to have a delay. middle or more expensive airlines are more reliable, comfortable, and have consistent pleasant staff working.
Verified travelerFlew with Alaska Airlines
SEA
-
DEN
Mar 2025
Alaska Air is very efficient & on-time so allow enough time to get luggage, go thru Customs & Immigration, & long security lines. Terminals in SEA are readily accessible by trains but more signage is needed. Fortunately, Information booths are everywhere & are manned by very helpful staff.
Verified travelerFlew with Air Canada
PHX
-
DEN
Apr 2025
All was great would surly book again and recommend Be on the ball and find gate before landing
Verified travelerFlew with Delta
LAX
-
DEN
Apr 2025
It’s an easy short flight, so a quick recharge nap is nice. A neck pillow is recommended.
MichaelFlew with Delta
SEA
-
DEN
Apr 2025
Train from Denver airport to downtown is easy to use.
MatthewFlew with Frontier
MSP
-
DEN
Mar 2025
Bring a seat cushion? The seats aren’t very comfortable.
DavidFlew with JetBlue
JFK
-
DEN
Jan 2025
JetBlue leaves from JFK which can be a plus or minus depending on your plans in New York. Arrive early and check out the TWA hotel—with a great public lounge, bar, and food court in the restored 1960’s Eero Saarinen-designed building outside of terminal 5. The AirTran accepts OMNY tap to pay with your phone or credit card, take it to Jamaica station to transfer to the LIRR to go to Penn Station in Manhattan or check the MTA TrainTime app for schedules and tickets for other destinations.
BrittanyFlew with United Airlines
RSW
-
DEN
Dec 2024
Prepare for a long flight and always have back up entertainment options prepared in case a different plane gets subbed before your flight with no notice.
DavidFlew with United Airlines
MKE
-
DEN
Dec 2024
Fill up water bottles at the fountain right after security (there’s only one water filler per concourse).
DanaFlew with United Airlines
ATL
-
DEN
Nov 2024
Bring your own headset if you want to plug into the in chair TV. They don’t have any to pass out.
MohanFlew with Frontier
RDU
-
DEN
Oct 2024
Check-in online and ensure your personal item is not big, these guys are a pain to deal with
MartyFlew with Alaska Airlines
ANC
-
DEN
Jun 2024
Try to book a red eye flight. Premium class is worth it if you like extra leg room.
kristenFlew with United Airlines
ASE
-
DEN
Jul 2024
weather can cause delays, and pack light if you chose to carry-on
AdrianFlew with United Airlines
ICT
-
DEN
Aug 2024
Don’t have your connection flight scheduled so close together
RogerFlew with United Airlines
HNL
-
DEN
Jun 2024
According to HNL gate agent arriving UA 1805 from Denver Is “infamously” late, so don’t take the redeye UA 1806 turn around flight unless your prepared to camp out in the airport and possibly miss connections on the US mainland
Verified travelerFlew with Lufthansa
PSP
-
DEN
Mar 2024
Palm Springs is beautiful airport, check in your tickets before arriving. Busy drop off but still manageable.
Verified travelerFlew with United Airlines
SFO
-
DEN
Mar 2024
Get TSA PRE and CLEAR. Life will be easy.
Verified travelerFlew with Alaska Airlines
SEA
-
DEN
May 2024
When flying from Seattle to Denver, be ready to take our any electronics and put them in separate bins when going through security. You will also most likely have to take off your jacket as well. During our flight back the flight randomly changed so be on the lookout in case that happens to you! It was by chance that I checked my ticket and saw that the gate changed last minute.
JoanneFlew with Air Canada
MSP
-
DEN
Apr 2024
It was not clear to me that my Air Canada flight would be handled by United, so I had some uncertainty about check-in. A United employee helped me check in eventually. Check for code-sharing partners.
MichaelFlew with United Airlines
LAX
-
DEN
Mar 2024
Arrive early if you have carry-on luggage. Eat before you get on the plane.
Verified travelerFlew with Air Canada
COS
-
DEN
Mar 2024
Make sure to have snacks and drinks with you if you need them.
Verified travelerFlew with United Airlines
GEG
-
DEN
Apr 2024
Time to switch planes should be more than 60 minutes.
Verified travelerFlew with Frontier
DCA
-
DEN
Dec 2023
Always check the rules and guidelines prior to boarding. Be early. Rest and eat before departure.
Verified travelerFlew with United Airlines
PSC
-
DEN
Feb 2024
TSA doesn't open til 1030 so getting to the airport early isn't helpful
RonaFlew with Delta
MSP
-
DEN
Feb 2024
The TSA line in Mpls was really long, give yourself alot of time.
JaredFlew with United Airlines
LBB
-
DEN
Feb 2024
Download everything before the flight. Make sure you can make your layover.
JeffreyFlew with Delta
JFK
-
DEN
Jan 2024
Leave a lot of time to get to your gate.
BrianFlew with United Airlines
SBP
-
DEN
Jan 2024
Don’t arrive too early since it’s a small airport.
KristofferFlew with United Airlines
ATL
-
DEN
Feb 2024
Check prices all the time as they fluctuate often

FAQs - booking Winter Park flights

  • How long is the flight to Winter Park?

    Flights from Phoenix2h 01m
    Flights from San Francisco2h 50m
    Flights from Minneapolis2h 08m
    Flights from Boston4h 19m
    Flights from Los Angeles2h 37m
  • What is the cheapest flight to Denver?

    In the last 3 days, the cheapest flight deal to Denver was found on the route from Dallas, at $58 return. The most popular connection is from Minneapolis to Denver and KAYAK users have found round-trip deals for as low as $68 in the last 3 days.

  • Which airlines fly to Denver?

    Many airlines fly to Denver, the most common ones being United Airlines, Southwest, and Frontier. See the amount of flights per week for popular airlines flying to Denver.

  • How to fly to Winter Park?

    You cannot fly directly to Winter Park. KAYAK recommends you fly to Denver Intl (DEN) (57.79 miles from Winter Park). From there you can rent a car or get a taxi.

  • What airports are near Winter Park?

    The closest airport is Denver Intl (DEN) (57.79 mi). Another nearby airport is Vail Eagle County (EGE) (63.67 mi). KAYAK recommends you fly to Denver Intl.

  • How far is Denver Intl Airport from central Denver?

    The city center of Denver is 18 miles from Denver Intl Airport.

  • What is the name of Denver’s airport?

    Denver is served by Denver Intl Airport, also commonly referred to as Denver or Denver Intl. The airport code is DEN.

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

    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 Winter Park.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winter Park 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 Winter Park?

    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 Winter Park 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 Winter Park?

    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 Winter Park 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 Winter Park

  • There is no major airport in Winter Park. It is instead served by Denver Intl Airport.
  • Looking for cheap airfare to Winter Park? 25% of our users found round-trip tickets to Winter Park for the following prices or less: From Los Angeles $425, from Boston $565, from Miami $679
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winter Park flight deals.

Reviews of the top 5 airlines flying to Winter Park

 
Need help choosing which airline to fly with from the United States to Winter Park? 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.
8.0
SouthwestOverall score based on 4301 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

As great a red-eye flight as red-eye flights can be.

Both of my flights arrived early and check in process was smooth

Everything was on time Will use united again for sure

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Hotter than Hades in August. Why, why do crews think that in the winter when we are already dressed for cold weather we need a cabin that is 82 degrees. Even the vents were blowing hot air.

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

Not good - outbound flight was delayed and missed my connection even though I got to the gate after running through the airport - the agent would not let me on because the door was closed (flight had not left). There was no notification from United - overall experience was very disappointing. Additionally, I was downgraded from first class to coach on the alternative flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

Lack of gluten free options in food service. I have Celiac disease and it appears you no longer offer special meals for people with dietary restrictions. I am a frequent flyer traveling into and out of Omaha airport. I have noticed over the course of several months that although our flight typically arrives ahead of schedule (awesome job AA!) - we typically sit on the runway for several minutes waiting for the ground crew to get in place. Not sure if it is a ground crew issue or a gate availability issue (due to construction at this airport). Seems to be more of a ground crew being on time issue.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Gate not determined until I got to the airport - hard to plan the trip to the airport.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

The experience was good. No frills but I got there safe and sound and on time.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Everything you need to know for your flight to Winter Park