Cheap flights To Winter Park (ORL) from $108

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Cheap Flights to Winter Park from $108 One Way, $198 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Nov 8 - Sat, Nov 15
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$198 Roundtrip, found 10 hours ago
$198
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Sat, Nov 8 from Punta Cana Intl. to Orlando Intl., returning Sat, Nov 15, priced at $198 found 10 hours ago
Fri, Nov 14 - Sun, Nov 16
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$226 Roundtrip, found 6 hours ago
$226
Roundtrip
found 6 hours ago
Select Arajet flight, departing Fri, Nov 14 from Punta Cana Intl. to Orlando Sanford Intl., returning Sun, Nov 16, priced at $226 found 6 hours ago
Sat, Nov 15 - Wed, Nov 19
KIN
Norman Manley Intl.
MCO
Orlando Intl.
$269 Roundtrip, found 17 hours ago
$269
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Norman Manley Intl. to Orlando Intl., returning Wed, Nov 19, priced at $269 found 17 hours ago
Fri, Nov 14 - Sun, Nov 16
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$320 Roundtrip, found 6 hours ago
$320
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Fri, Nov 14 from Punta Cana Intl. to Orlando Intl., returning Sun, Nov 16, priced at $320 found 6 hours ago
Wed, Nov 19 - Thu, Nov 27
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$335 Roundtrip, found 14 hours ago
$335
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, Nov 19 from Punta Cana Intl. to Orlando Intl., returning Thu, Nov 27, priced at $335 found 14 hours ago
Sat, Nov 22 - Tue, Nov 25
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 22 from Punta Cana Intl. to Orlando Intl., returning Tue, Nov 25, priced at $339 found 1 day ago
Fri, Mar 13 - Tue, Mar 24
GRU
Guarulhos - Governor André Franco Montoro Intl.
SFB
Orlando Sanford Intl.
$370 Roundtrip, found 1 hour ago
$370
Roundtrip
found 1 hour ago
Select Arajet flight, departing Fri, Mar 13 from Guarulhos - Governor André Franco Montoro Intl. to Orlando Sanford Intl., returning Tue, Mar 24, priced at $370 found 1 hour ago
Wed, Nov 19 - Thu, Nov 27
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$371 Roundtrip, found 14 hours ago
$371
Roundtrip
found 14 hours ago
Select Copa flight, departing Wed, Nov 19 from Punta Cana Intl. to Orlando Intl., returning Thu, Nov 27, priced at $371 found 14 hours ago
Thu, Dec 4 - Wed, Dec 10
LIM
Jorge Chávez Intl.
MCO
Orlando Intl.
$413 Roundtrip, found 1 day ago
$413
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Dec 4 from Jorge Chávez Intl. to Orlando Intl., returning Wed, Dec 10, priced at $413 found 1 day ago
Tue, Dec 2 - Fri, Dec 5
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$426 Roundtrip, found 1 day ago
$426
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Punta Cana Intl. to Orlando Intl., returning Fri, Dec 5, priced at $426 found 1 day ago

Winter Park Flight Information

Traveling To
Winter Park
Destination Airport IATA Code
ORL
Number of Airlines Serving
Airlines
Spirit Airlines, Arajet, Southwest Airlines, JetBlue Airways, American Airlines, Copa, Delta, World Ticket Ltd
Flight Price
$198
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

Dec 1 - Dec 3

2 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Boston (BOS)

Breeze Airways • Coach
Price was $367, price is now $170 per person
$170
per person
found 1 day ago
Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

Dec 20 - Dec 25

5 night stay

Minneapolis (MSP) to Orlando (MCO)

Sun Country Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,624, price is now $903 per person
$903
per person
found 1 day ago
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Dec 17 - Dec 24

7 night stay

Boston (BOS) to Orlando (MCO)

Breeze Airways • Roundtrip • Coach
Price was $838, price is now $427 per person
$427
per person
found 1 day ago
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See all available trips from Boston to Winter Park
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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (2,167 reviews)

Dec 3 - Dec 7

4 night stay

San Juan (SJU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,223, price is now $953 per person
$953
per person
found 22 hours ago
We love Florida Hotel, it is right inside the mall which made our stay enjoyable. The room is spacious and cozy and what really made us love the Hotel is the staff who are very attentive to us. Mr. Ted Kopsaftis was very helpful and he has a heart of gold for his unwaivering assistance with my return packages to amazon. I would have been miserable without his help. He went above and beyond helping me settle my problem with amazon. Thank you Florida Hotel for having an amazing staff.

Reviewed on Feb 4, 2025

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,019 reviews)

Dec 3 - Dec 7

4 night stay

San Juan (SJU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,346, price is now $1,096 per person
$1,096
per person
found 22 hours ago
Great location for hospital access

Reviewed on Jul 8, 2025

Villatel Orlando Resort
4.0-star property

Villatel Orlando Resort

9.4/10 Exceptional! (237 reviews)

Dec 3 - Dec 7

4 night stay

San Juan (SJU) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,835, price is now $1,589 per person
$1,589
per person
found 22 hours ago
If you're looking for a quiet AIR B&B style house to stay in, this is it. So nice to be in a quiet non crowded place to rest and relax.

Reviewed on Feb 3, 2025

Don't see what you're looking for?
See all available trips from San Juan to Winter Park
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Winter Park

Struggling to find international and domestic flights that suit your budget. Consider one of the cheaper options available when you book your flight with Orbitz, where you get guaranteed low prices

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You can now book flights to Winter Park on the new cutting-edge mobile tool for Android or iPhone users. Hotel packages, flight updates and changes can all be accessed using this tool. When you make any reservations or bookings using this service, confirmation will be provided on the same day the request was made. Take advantage of Orbitz friendly service and low cost Winter Park flights.

Discounted tickets available for flights to Winter Park

Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Winter Park flights with us and structure a package that includes car hire, family activities and cheap accommodation. Orbitz will ensure that all your requirements are met, letting you relax and enjoy your holiday as it was intended.

Orbitz offers discounted Winter Park flights

Discounted flights to Winter Park ensure that all who want to travel can Take advantage of Orbitz’ guaranteed low prices and affordable packages. You will enjoy a hassle free trip, an up to date travel planner and friendly service.

Traveler profile updates

When flying with Orbitz, take advantage of frequent updates on your flights to Winter Park. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Winter Park flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

Frequently asked questions

Which airlines fly to Winter Park?
With 20 airlines offering services to Orlando Intl. Airport (MCO), the main entry point to Winter Park, the choice is all yours. Grab an incredible deal among these top international airlines that'll take you to this city:

  • Spirit Airlines - 274 flights to Winter Park per month
  • JetBlue - 148 flights to Winter Park per month
  • Frontier Airlines - 105 flights to Winter Park per month

What is the best airport to fly to in Winter Park?
Orlando Intl. Airport (MCO) is the entry point to the city, so your toughest decision will be the aisle seat or the window seat. Downtown Winter Park is around 12 miles away and where many visitors kick off their adventure.
How much is a flight to Winter Park?
Prices for return flights to Winter Park this last week fluctuated between $198 and $426. If you were flying one-way from Punta Cana (PUJ), you could have nabbed fares from just $108.
How to book the cheapest flight to Winter Park?
With Orbitz, you'll uncover some of the most affordable flight deals around from a great range of airlines. But if you'd love to heighten your chances of landing cheap flights to Winter Park, here are some tips to bear in mind:

  • Consider alternative airports to increase your savings. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list the available options.
  • If you're flexible with your plans, click on the 'Show flexible dates' option. It'll bring up flight deals for the days either side of your selected departure. Fares often vary depending on the day of the week.
  • To refine your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also select your preferred flight times under 'Sort & Filter' to the left.
  • If you've worked out your travel dates, don't waste time booking your flight. Fares normally get more expensive as the departure date gets closer.
  • Consider bundling your flights, hotels and car rental into a package deal with Orbitz — the more you book, the more you save.
  • Whenever possible, don't travel in peak seasons. Airfares often surge during summer, school breaks and other vacation periods like Thanksgiving and Christmas.

How long is a flight to Winter Park?
The length of your flight will depend on where you're jetting in from, whether that's the East Coast, the West Coast or someplace else. Listed below are three of the busiest routes to Winter Park and average flight times:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Orlando Intl. Airport (MCO) - 1 hour and 46 minutes
  • Newark, NJ (EWR-Liberty Intl.) to Orlando Intl. Airport (MCO) - 2 hours and 50 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Orlando Intl. Airport (MCO) - 2 hours and 38 minutes

What is the best time to book a flight to Winter Park?
Generally speaking, the cheapest time to book a seat is January. This is followed by February then August. When searching for a cheap flight to Winter Park, it's worth being ready to book. Cheap deals pop up suddenly and don't hang around!
What day of the week is the cheapest to book a flight to Winter Park?
If you're after inexpensive fares to Winter Park, the best days of the week to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a terrific flight deal will be all yours.
What is the cheapest day of the week to fly to Winter Park?
Look into going early in the week if you want to score cheap flights to Winter Park. Orbitz data from 2020 shows Monday is generally the cheapest day to set off, followed by Tuesday. Saturday was found to have the most expensive ticket fares. This is probably because most passengers choose to begin their getaway when the weekend rolls around.
What is the cheapest month to fly to Winter Park?
To secure cheap flights to Winter Park, you should depart in August. If saving on your ticket is your number one priority, Orbitz data shows that this is generally an excellent month to take a trip. June is when fares are at their peak.
Which airlines allow free cancellation?
When searching for flights on Orbitz, click on "Filter by flexible change policies." This filter will quickly find all the carriers offering free cancellation and no change fees. Relax knowing that if your travel dates change, your reservation can too.
What do I need for the flight to Winter Park?
Flying doesn't have to be a drag. In fact it can be fun if you're well prepared! Make your journey a total breeze with these practical tips:

  • Before you step foot on the plane, you'll need to show proof of identification, like your passport. You'll also need your ticket. If you're traveling with the kids, check with your airline about which documents they may need.
  • Take some activities to pass the time on your trip to Winter Park. Books, magazines and electronic devices like e-readers and tablets should do the trick. Be sure to take a refillable water bottle too. Even on a short flight, it's important to keep well-hydrated.
  • It can get cool on the plane. If you'd rather not shiver your way through the flight, pack an extra layer.

How many direct flights are there to Winter Park?
There are 1,109 flights that travel straight to Winter Park every month, which means you won't have to stress over long stopovers. Reserve a fare with Southwest Airlines or Spirit Airlines and then settle back and enjoy the flight. Frontier Airlines, Delta Air Lines, JetBlue Airways and American Airlines also provide nonstop flights to Winter Park.
How do I get cheap first-class/business deals to Winter Park?
Savvy travelers have a way of finding first or business-class fares to Winter Park that don't cost an arm and a leg. Take their lead with these useful hints:

  • Flexibility isn't just useful for your yoga. Avoid locking in your travel dates so you can snap up cheaper airfares when a big sale drops.
  • Budget airlines offer business-class seats at a fraction of the normal price. Ditch the full-service carriers and go with one of these cheaper options.
  • Take advantage of your airline's flight rewards program and upgrade your seat. You can also bid for an upgrade in an online auction.

How to get into Winter Park from the airport?
Make things easier with an Orlando Intl. Airport (MCO) car rental. Arrive at Orlando Intl. Airport (MCO) and then collect a set of wheels from one of the two outlets on-site. Enterprise and EZ Rent-A-Car both have a terrific variety of vehicles to choose from. After you've buckled up, you'll need to travel approximately 12 miles to the north to make it to the excitement of central Winter Park. Renting a car from the city center is another popular option with unbeatable deals available from Winter Park car rentals.
What is the best time to go to Winter Park?
People come from every direction to visit Winter Park in March, July and August. So if you want to discover this exciting destination in the tourist season, this is the time to go. Like most places in the Northern Hemisphere, the summer begins June 20 in Winter Park, with average daily temperatures between 75 ºF and 90 ºF.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.