$28 Cheap Flights to Winter Park, FL

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Popular airlines to Winter Park

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Today's featured flight deals to Winter Park

Nonstop
Carry-on included
Lower price than typical

How much is the cheapest flight to Winter Park?

Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Mar 7 - Tue, Mar 10
SJU
San Juan
MCO
Orlando
$166 Roundtrip, just found
$166
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Mar 7 from San Juan to Orlando, returning Tue, Mar 10, priced at $166 just found
Frontier Airlines
Sat, Mar 14 - Sat, Mar 21
PUJ
Punta Cana
MCO
Orlando
$182 Roundtrip, just found
$182
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Mar 14 from Punta Cana to Orlando, returning Sat, Mar 21, priced at $182 just found
Arajet
Fri, Apr 10 - Tue, Apr 14
PUJ
Punta Cana
SFB
Orlando
$211 Roundtrip, found 2 days ago
$211
Roundtrip
found 2 days ago
Select Arajet flight, departing Fri, Apr 10 from Punta Cana to Orlando, returning Tue, Apr 14, priced at $211 found 2 days ago
Delta
Fri, Apr 17 - Tue, Apr 21
SJU
San Juan
MCO
Orlando
$256 Roundtrip, found 2 hours ago
$256
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Apr 17 from San Juan to Orlando, returning Tue, Apr 21, priced at $256 found 2 hours ago
JetBlue Airways
Sat, Sep 26 - Sun, Sep 27
SJU
San Juan
MCO
Orlando
$280 Roundtrip, found 1 hour ago
$280
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Sep 26 from San Juan to Orlando, returning Sun, Sep 27, priced at $280 found 1 hour ago

Alternative airports near Winter Park

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Orlando Intl. MCO. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $259
MCO
Orlando Intl.
Cheapest
Average driving time to city center23 min
Flights from $259

Find the cheapest month to fly from Columbus (CMH) to Orlando (MCO)

January is typically the cheapest month to fly

From $40 - $164 per traveler.

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Frequently asked questions

What month is the cheapest to fly to Winter Park?
September is the most affordable month to fly to Winter Park, with average fares around $407. This month often sees less travel activity, which can lead to better prices. You may also find reasonable fares in January, February, and May.*Prices based on flights available on Expedia in the last year.
Which US cities have the cheapest flights to Winter Park?
You can find some of the cheapest flights to Winter Park from these US cities:

  • New Haven (HVN)
  • Latrobe (LBE)
  • Portsmouth (PSM)
  • Newburgh (SWF)
  • Trenton (TTN)

with fares typically starting around $32.
Which US cities fly direct to Winter Park?
Direct flights to airports near Winter Park are available from these US cities:To Orlando Intl. (MCO)
  • Newark (EWR)
  • New York (JFK, LGA)
  • Chicago (MDW, ORD)
  • Philadelphia (PHL)
  • Boston (BOS)

To Tampa Intl. (TPA)
  • Newark (EWR)
  • New York (JFK, LGA)
  • Chicago (MDW, ORD)
  • Philadelphia (PHL)
  • Atlanta (ATL)

To Daytona Beach Intl. (DAB)
  • New York (JFK, LGA)
  • Boston (BOS)
  • Atlanta (ATL)
  • Charlotte (CLT)
  • Hartford (BDL)

How to find a cheap flight to Winter Park?
To find a cheap flight to Winter Park, be flexible with your dates. Traveling in the off-season or shoulder season can help you save. Mid-week flights are usually less expensive, too. Use flight search engines, like Expedia, to compare airlines, flight times and routes all in one place to find affordable rates. You may find that flights with layovers are cheaper than direct flights. You can also set up Price Tracking and receive alerts when fares go up or down.
Which airlines fly to Winter Park?
Multiple carriers fly to Winter Park:

  • American Airlines
  • Delta
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue Airways
  • Spirit Airlines
  • United

Where do you fly into Winter Park?
If you're heading to Winter Park, you have several airport options:

  • The closest major airport is Orlando, FL (MCO-Orlando Intl.), about 12 miles from the city center, which is a hub for American Airlines, United, and Frontier Airlines, with other airlines like Delta, WN also operating here.
  • Tampa, FL (TPA-Tampa Intl.) is another option, about 93 miles away, serving as a hub for American Airlines, Delta, and United, with Frontier Airlines, WN also operating here.
  • Daytona Beach, FL (DAB-Daytona Beach Intl.), about 45 miles away, serving as a hub for Delta, American Airlines, and JetBlue Airways, with MX, KLM also operating here.
  • Gainesville, FL (GNV-Gainesville Regional), about 99 miles away, serving as a hub for Delta, American Airlines, and MQ, with OH, Aeromexico also operating here.
  • Melbourne, FL (MLB-Orlando Melbourne Intl.), about 60 miles away, serving as a hub for Delta and American Airlines.

What is the cheapest airport to fly to in Winter Park?
The most budget-friendly airport to fly into Winter Park is usually Orlando, FL (MCO-Orlando Intl.), located approximately 12 miles from the city center. This proximity makes it a convenient choice for travelers.*Prices based on flights available on Expedia in the last year.
Which budget airlines fly to Winter Park?
For budget travel to Winter Park, there are 14 low-cost airlines to choose from, including:

  • Frontier Airlines: serves Orlando (MCO), Tampa (TPA)
  • Spirit Airlines: serves Orlando (MCO), Tampa (TPA)
  • Southwest Airlines: serves Orlando (MCO), Tampa (TPA)
  • JetBlue Airways: serves Orlando (MCO), Daytona Beach (DAB), Tampa (TPA)
  • Breeze: serves Orlando (MCO), Daytona Beach (DAB), Tampa (TPA)
  • WestJet: serves Orlando (MCO), Daytona Beach (DAB), Melbourne (MLB), Tampa (TPA), Gainesville (GNV)
  • Sun Country Airlines: serves Orlando (MCO), Tampa (TPA)
  • Volaris: flies to Orlando (MCO)
  • Azul: flies to Orlando (MCO)
  • Flair Airlines: flies to Orlando (MCO)

What is the best month to visit Winter Park?
The best month to visit Winter Park depends on your priorities, whether you want ideal weather, fewer crowds, or the lowest prices. If affordability matters most, look for cheap March flights outside of peak season.
How far in advance should I book a flight to Winter Park?
For domestic travel to Winter Park, booking around 1 month in advance can help you find the best prices. For international flights to Winter Park, aim to book around 1 month ahead to get cheaper fares. For added peace of mind, use Expedia's Price Drop Protection™ when you make your booking. It's free to use for Gold and Platinum members on the Expedia app. Once a qualifying flight is purchased, we'll automatically check your flight on Expedia until the day of your departure and notify you if there are price changes. If your flight price drops after you book, we'll automatically award the price difference in OneKeyCash™* into your One Key account after your trip ends.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What day of the week is cheapest day to buy a plane ticket to Winter Park?
Friday is typically the cheapest day to buy a plane ticket to Winter Park, with an average price of around $430.44. This lower fare is often due to reduced demand as many travelers fly on weekends. If Friday doesn't fit your schedule, consider looking at flights on Thursday. Use Expedia's Price Tracking tool to monitor prices for your trip and receive alerts when fares go up or down.*Cheapest day to book based on flights available on Expedia in the last year.
What is the most expensive month to fly to Winter Park?
December is typically the most expensive month to fly to Winter Park, with average return ticket prices around $511. This is about 13% higher than the average throughout the year, as holiday travel demand peaks during this festive season. If you're looking to save, consider visiting in January or August when prices tend to be lower.*Prices based on flights available on Expedia in the last year.
What public holidays or seasonal events might make flights to Winter Park more expensive?
If you're considering a visit to Winter Park, be aware that flights can be more expensive during peak holiday periods. For Winter Park, Colorado, expect higher prices around New Year's, Martin Luther King Jr. Day in January, and President's Day in February. For Winter Park, Florida, spring break in mid-March to early April and the holiday season from late December to early January also see increased travel costs.
How far is the airport from central Winter Park?
There are 2 airports serving Winter Park:

  • Orlando, FL (MCO-Orlando Intl.): 9 miles southeast
  • Orlando, FL (SFB-Orlando Sanford Intl.): 19 miles northeast

These options give you flexibility when planning your trip.
How can I track flight prices to Winter Park?
Our Price Tracking tool allows you to monitor fares to Winter Park. You can view flight price history and see predictions of future prices as available. When you're signed into your Expedia account, you can set up flight price alerts too. This way, you'll receive notifications when prices go up or down, so you know when it's the right time to book.
How to get a cheap last-minute flight to Winter Park?
It is possible to find cheap, last-minute flights to Winter Park, especially if you can be flexible with your dates, times and route. Whether you're planning a spontaneous getaway or need to travel for business, there are plenty of last-minute flight deals on Expedia. You can also bundle your flight and hotel for even more savings with a package deal.
Can I earn miles booking a flight to Winter Park with Expedia?
You can earn miles when booking a flight to Winter Park on Expedia. Before confirming your booking, just select the frequent flyer program name and enter your program number. For even more rewards, join One Key™—our free travel rewards program. One Key members earn OneKeyCash™* on eligible bookings for every dollar spent.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Can I save money by booking a Winter Park trip package?
Book a Winter Park flight and hotel package deal on Expedia, and you can make significant savings. It's simple to bundle your accommodations and flights, and you can also add car rentals and activities to create your own customized Winter Park trip. Plus, nothing beats the convenience of booking everything in the same place.
Can I change or cancel my flight to Winter Park?
It's often possible to cancel or change your flight to Winter Park using Expedia. Many airlines let you cancel your flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may offer to reschedule your flight rather than provide a direct refund. To find affordable flights to Winter Park with flexible change policies, select "No cancel fee" or "Changes included" when you search. Need more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

Book with confidence

Tips to find the cheapest flights to Winter Park

The cheapest day to fly

Get started finding a cheap flight to Winter Park on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

March is the cheapest month to fly to Winter Park. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Winter Park. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Winter Park, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Winter Park

The lowest price for round-trip flights to Winter Park in 2026 starts from from $56, while one-way tickets start from from $28. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Winter Park. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winter Park

Spirit Airlines, Frontier Airlines, Arajet, Delta, JetBlue Airways are just some of the airlines that can typically offer cheap tickets to Winter Park. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Winter Park and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Winter Park, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Winter Park. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Winter Park plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Winter Park

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Winter Park.

Stopover savings

The cheapest tickets to Winter Park are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Winter Park. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Winter Park for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Winter Park. Simply download the free Expedia app to your smart device and activate Winter Park flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Winter Park. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Tips to find the cheapest flights to Winter Park

Travel information

Destination airport
Orlando Intl.
Destination airport IATA code
MCO
Destination city name
Orlando
Roundtrip price
$165

Trending flights to Winter Park

Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Apr 20 - Fri, Apr 24
PHL
Philadelphia
MCO
Orlando
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Apr 20 from Philadelphia to Orlando, returning Fri, Apr 24, priced at $56 just found

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*Available to One Key members.