Cheap Flight Deals to Winter Park FL from CA $130

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Winter Park?

The cheapest prices found with in the last 7 days for return flights were CA $70 and CA $130 for one-way flights to Winter Park for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSOrlandoMay 13 to May 21CA $70
PHLOrlandoApril 5 to April 12CA $84
LGAOrlandoApril 23 to April 30CA $91
DTWOrlandoMarch 31 to April 2CA $104
ORDOrlandoApril 2 to April 7CA $112
EWROrlandoMarch 30 to April 8CA $119
SJUOrlandoMarch 29 to April 5CA $151
MSPOrlandoMarch 27 to April 2CA $176
JFKOrlandoMarch 25 to April 4CA $197
LAXOrlandoApril 30 to May 12CA $212
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
DTWOrlandoMarch 16 to March 20CA $154
BOSOrlandoMarch 16 to March 20CA $169
LGAOrlandoMarch 16 to March 29CA $185
SJUOrlandoMarch 15 to March 31CA $192
EWROrlandoMarch 15 to March 18CA $207
JFKOrlandoMarch 16 to March 18CA $221
MSPOrlandoMarch 16 to March 23CA $346
PHLOrlandoMarch 15 to March 16CA $380
ORDOrlandoMarch 15 to March 26CA $441
LAXOrlandoMarch 14 to March 17CA $493
*Prices include taxes and fees

Your guide to flights to Winter Park, FL

Flair Airlines, Bahamasair fly to Winter Park, so use Travelocity to search, find, and compare some truly tempting deals from the 4 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 $70 and CA $884. Prices vary, but for the best fares, travel in April 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 $70. 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 April 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

The Alfond Inn

4 out of 5
300 East New England Avenue, Winter Park, FL
The price is CA $431 per night from Mar. 16 to Mar. 17
CA $431
CA $517 total
includes taxes & fees
16 Mar - 17 Mar
Stay at this 4-star spa hotel in Winter Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (1,007 reviews)
"The artwork in public places and the rooms….extraordinary!"

Reviewed on 27 Feb. 2025

The Alfond Inn
Park Plaza Hotel

Park Plaza Hotel

3 out of 5
307 South Park Avenue , Winter Park, FL
The price is CA $218 per night from Apr. 2 to Apr. 3
CA $218
CA $245 total
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3-star spa hotel in Winter Park. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff and the property condition ...
8.4/10 Very Good! (938 reviews)
Back in Time on Park Ave.
"Staying in Winter Park on Park Ave is a defined treat for adults. Lodging with Park Plaza Hotel was fun but the rooms needs updating in the bathrooms - old shower heads, non-enviromental toiletries, toilets that are pulling away from the walls, all speak to a refresh for the price. It's charm is ..."

Reviewed on 6 Mar. 2025

Park Plaza Hotel
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.

Family Friendly Hotels in Winter Park

The Alfond Inn

The Alfond Inn

4 out of 5
300 East New England Avenue, Winter Park, FL
The price is CA $431 per night from Mar. 16 to Mar. 17
CA $431
CA $517 total
includes taxes & fees
16 Mar - 17 Mar
Stay at this 4-star spa hotel in Winter Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.4/10 Exceptional! (1,007 reviews)
"The artwork in public places and the rooms….extraordinary!"

Reviewed on 27 Feb. 2025

The Alfond Inn
Park Plaza Hotel

Park Plaza Hotel

3 out of 5
307 South Park Avenue , Winter Park, FL
The price is CA $218 per night from Apr. 2 to Apr. 3
CA $218
CA $245 total
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3-star spa hotel in Winter Park. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff and the property condition ...
8.4/10 Very Good! (938 reviews)
Back in Time on Park Ave.
"Staying in Winter Park on Park Ave is a defined treat for adults. Lodging with Park Plaza Hotel was fun but the rooms needs updating in the bathrooms - old shower heads, non-enviromental toiletries, toilets that are pulling away from the walls, all speak to a refresh for the price. It's charm is ..."

Reviewed on 6 Mar. 2025

Park Plaza Hotel
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.

Best Winter Park Flight and Hotel Packages

Winter Park flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate River Ranch Resort & Rodeo
Westgate Palace Hotel / Universal / I-Drive
Harbor Island Beach Club by Villatel
Don't see what you're looking for?
See all available trips from Montreal to Winter Park
View all trips

Winter Park flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Westgate Palace Hotel / Universal / I-Drive
Hilton Daytona Beach Oceanfront Resort
Don't see what you're looking for?
See all available trips from Toronto to Winter Park
View all trips

Winter Park flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Margaritaville Cottages Orlando by VStays
ette hotel
Don't see what you're looking for?
See all available trips from Vancouver to Winter Park
View all trips

Need a car after flight to Winter Park?

Frequently asked questions

Which airlines fly to Winter Park?
20 airlines advertise flights to Winter Park, making it one of the world’s most frequented airline hubs. Lots of seasoned travelers fly with these carriers:

  • Southwest Airlines
  • Spirit Airlines
  • Delta Air Lines

What airport is best to fly into Winter Park?
Flying in and out of Winter Park is simple, as it has just one airport. You’ll find MCO approximately 19 kilometers from all the action downtown.
Where to stay in Winter Park
Life is one big journey, so why not get out there and really experience it in Winter Park? You can start by choosing from the 870 superb properties available there through Travelocity.Your vacation is here! It’s the perfect time to treat yourself to life’s little luxuries. Make a reservation at the The Alfond Inn or the Hilton Orlando/Altamonte Springs and enjoy outstanding service and a lavish room. The Days Inn by Wyndham N Orlando/Casselberry and the HomeTowne Studios by Red Roof Orlando - Casselberry are some less expensive options if you’d prefer to spend your cash on activities and experiences.
Places to visit in Winter Park
0 Seeking some more ideas? 0 But there’s more. 0
How to get through airport security fast when traveling to Winter Park
These handy tips and hints about airport security will save you lots of time and energy on your way to Winter Park:

  • Have your boarding pass and travel ID easily accessible. They’ll be the first things you’ll be instructed to produce by security personnel.
  • Keep in mind that metal belt buckles can set off the body scanner’s alarms. If you have one on, you may be instructed to step back and remove it before proceeding.
  • Laptops and other electronic devices must be placed in a tub to be X-rayed.
  • When it comes to flying with liquids and gels, every passenger is permitted a quart-sized clear zip-lock bag to transport containers no greater than 3.4 ounces (100 milliliters).
  • Hiking boots and other cumbersome shoes tend to be X-rayed by airport security. We suggest wearing simple sneakers instead.
  • Razors and knives are prohibited from entering the aircraft. Stash them away in your checked luggage to avoid losing them at the airport security checkpoint.

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!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.