Cheap Flights to Winter Park
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| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ORD | Orlando | July 14 to July 21 | $115 |
| SWF | Orlando | August 30 to September 3 | $127 |
| PSM | Orlando | August 29 to September 3 | $149 |
| PHL | Orlando | August 30 to September 3 | $162 |
| EWR | Orlando | September 1 to September 9 | $167 |
| MSP | Orlando | September 2 to September 7 | $203 |
| LAX | Orlando | July 7 to July 14 | $211 |
| JFK | Orlando | August 29 to September 6 | $222 |
| DTW | Orlando | August 18 to August 26 | $240 |
| SJU | Orlando | July 7 to July 14 | $256 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SWF | Orlando | May 30 to June 12 | $160 |
| PSM | Orlando | May 30 to June 18 | $172 |
| PHL | Orlando | May 30 to June 3 | $214 |
| ORD | Orlando | May 30 to August 2 | $306 |
| EWR | Orlando | May 31 to June 6 | $337 |
| MSP | Orlando | May 31 to June 7 | $357 |
| JFK | Orlando | May 30 to June 1 | $374 |
| SJU | Orlando | May 30 to June 4 | $379 |
| DTW | Orlando | May 31 to June 4 | $408 |
| LAX | Orlando | May 31 to June 2 | $541 |
Winter Park Flight Information
Traveling to | Winter Park |
|---|---|
Lowest Price | $115 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Breeze Airways, JetBlue Airways, Southwest Airlines, Delta |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Luxury Hotels in Winter Park
The Alfond Inn
300 East New England Avenue Winter Park FL
$314 nightly
The price is $353 total per night from May 29 to May 30
$353 total
May 29 - May 30
Total with taxes and fees
Book a stay at this luxury hotel in Winter Park. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
9.6/10 Exceptional! (1,001 reviews)
"Absolutely stunning hotel! Clean, fancy and beautiful. Perfect for our family of 4 getaway. Our boys are ages 4 and 6 and loved the pool and sidewalks for walking/riding their bikes. Staff was very helpful and hospitable."
Reviewed on May 27, 2026
Park Plaza Hotel
307 South Park Avenue Winter Park FL
$216 nightly
The price is $243 total per night from Jun 7 to Jun 8
$243 total
Jun 7 - Jun 8
Total with taxes and fees
Book a stay at this golf hotel in Winter Park. Enjoy free WiFi, room service, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
"Old hotel, small rooms with minimal amentities. We arrived a day early by mistake. My error. They, however, would not let us use our reservation the day we arrived even though they had the same room available and made us pay for an additional day. We stayed one night and had to pay for two."
Reviewed on May 28, 2026
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
300 East New England Avenue Winter Park FL
The price is $353 total per night from May 29 to May 30
$353 total
per night
May 29 - May 30
Book a stay at this luxury hotel in Winter Park. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
9.6/10 Exceptional! (1,001 reviews)
"Absolutely stunning hotel! Clean, fancy and beautiful. Perfect for our family of 4 getaway. Our boys are ages 4 and 6 and loved the pool and sidewalks for walking/riding their bikes. Staff was very helpful and hospitable."
Reviewed on May 27, 2026
Park Plaza Hotel
307 South Park Avenue Winter Park FL
The price is $243 total per night from Jun 7 to Jun 8
$243 total
per night
Jun 7 - Jun 8
Book a stay at this golf hotel in Winter Park. Enjoy free WiFi, room service, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
"First time to book hotels.com. Termites in room on bed. Showed staff and they agreed it was termites. They said they would credit one night. More termites Saturday and Sunday. Will not book with hotels.com. Great location and nice staff but hotel very old. No water in room, no safe and old elevator ..."
Reviewed on May 26, 2026
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.
Winter Park flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from San Juan to Winter Park
View all tripsWinter Park flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Winter Park
View all tripsNeed a Car For After Your Flight?
Special
ORLANDO, USA
$1
$18 total
found 15 hours ago
Compact
Orlando, USA
$4
$8 total
found 15 hours ago
Economy
Orlando, USA
$4
$8 total
found 15 hours ago
Midsize
Orlando, USA
$5
$10 total
found 5 hours ago
Lowest prices found within the past 15 hours. Prices and availability subject to change. Additional terms may apply.
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!
More Ways To Wander
Winter Park Hotels
Find the perfect hotel after your flight
Winter Park Vacation Rentals
Great Deals on alternative accommodations
Winter Park Car Rentals
Affordable cars to get you around town
Winter Park Vacations
Save more by combining flights, hotels and cars
Things to do in Winter Park
Activities, attractions and tours
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