Cheap Flight Deals to Winter Park FL from CA $156
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How to find cheap flights to Winter Park?
The cheapest prices found with in the last 7 days for return flights were CA $167 and CA $156 for one-way flights to Winter Park for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| PSM | Orlando | October 24 to October 31 | CA $167 |
| SWF | Orlando | September 23 to October 1 | CA $221 |
| SJU | Orlando | September 27 to October 14 | CA $272 |
| DTW | Orlando | November 14 to November 17 | CA $275 |
| MSP | Orlando | November 18 to November 24 | CA $285 |
| EWR | Orlando | November 9 to November 17 | CA $286 |
| JFK | Orlando | October 6 to October 10 | CA $302 |
| ORD | Orlando | November 18 to November 19 | CA $327 |
| PHL | Orlando | October 26 to October 31 | CA $431 |
| LAX | Orlando | October 27 to October 31 | CA $436 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| SJU | Orlando | August 30 to September 1 | CA $399 |
| PSM | Orlando | August 29 to September 3 | CA $409 |
| SWF | Orlando | August 29 to September 2 | CA $469 |
| LAX | Orlando | August 30 to September 9 | CA $508 |
| ORD | Orlando | August 30 to September 1 | CA $525 |
| EWR | Orlando | August 30 to September 2 | CA $608 |
| JFK | Orlando | August 29 to September 6 | CA $654 |
| MSP | Orlando | August 30 to September 6 | CA $655 |
| PHL | Orlando | August 30 to September 2 | CA $744 |
| DTW | Orlando | August 29 to September 6 | CA $1,226 |
Your guide to flights to Winter Park, FL
Southwest Airlines, Flair Airlines fly to Winter Park, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winter Park FL currently costs between CA $167 and CA $1,226. Prices vary, but for the best fares, travel in September when prices are at their lowest.
Top tips for finding cheap flights to Winter Park
The cheapest flight for a round trip to Winter Park is currently CA $167. When you search for flights to Winter Park, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winter Park for nearby days. The cheapest month to travel to Winter Park is November from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Winter Park
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Winter Park with Travelocity
We have top deals on plane tickets even for last minute flights to Winter Park, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winter Park for less.
Find The Perfect Hotel For After Your Flight
Luxury Hotels in Winter Park
The Alfond Inn
"I already reviewed this on my other stay, so I won't repeat the review."
Reviewed on Aug 26, 2026
Park Plaza Hotel
"Balcony was key over looking the rose garden & park. Location is perfect across the street from gelato open late. We’ll be back for Christmas"
Reviewed on Aug 26, 2026
Family Friendly Hotels in Winter Park
The Alfond Inn
"I already reviewed this on my other stay, so I won't repeat the review."
Reviewed on Aug 26, 2026
Park Plaza Hotel
"Balcony was key over looking the rose garden & park. Location is perfect across the street from gelato open late. We’ll be back for Christmas"
Reviewed on Aug 26, 2026
Best Winter Park Flight and Hotel Packages
Winter Park flight + hotel packages - economy flights
Winter Park flight + hotel packages - business class flights
Winter Park flight + hotel packages - first class flights
Need a car after flight to Winter Park?
Economy
Compact
Midsize
SUV
Frequently asked questions
Plane Tickets To Winter Park
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winter Park. Browse through our inventory to explore a wide range of cheap flights to Winter Park to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winter Park as you anxiously await to exit the plane and explore what Winter Park has to offer. Considering all the amazing local food and culture in Winter Park, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winter Park to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winter Park without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winter Park with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winter Park today!
Need more than a Flight to Winter Park?
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