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$22 Cheap Flights to Winter Park, FL

View $22 flight on Mon, Oct 19, 2026Opens in a new window

Popular airlines to Winter Park

How much is the cheapest flight to Winter Park?

Prices were available within the past 7 days and start at $22 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Allegiant Air
Frontier Airlines
Breeze Airways
Delta
American Airlines

Alternative airports near Winter Park

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

What you need to know for your flight to Winter Park

Flights to Winter Park at a glance

Traveling to Winter Park is easy; simply choose between full-service and budget airlines, compare travel times, and select the flights to Winter Park that fit your budget and itinerary. Get ready to explore the city’s renowned attractions and charming neighborhoods!

  • Major airports near Winter Park: Orlando International Airport (MCO), Orlando Sanford International Airport (SFB)
  • Closest (typical) airport to Winter Park: Orlando International Airport, MCO (around 12 miles)
  • Flights per week: 7,400+ flights arriving across Winter Park airports
  • Number of airlines that fly to Winter Park: around 75+ carriers

Popular airports near Winter Park

Winter Park is a vibrant city perfect for family outings, entertainment, and urban getaways. Visitors are drawn to Winter Park for its rich outdoor experiences, cultural attractions, and business opportunities. The city is conveniently accessible via two major airports, including MCO Airport and nearby options.

  • Orlando International Airport (MCO): Situated in Orange County, Florida, approximately 12 miles from Winter Park, this airport facilitates both domestic and international flights, linking to roughly 300 domestic cities and 245 international locations. Travelers can opt for enhanced comfort by upgrading to first class, premium economy, or business class, depending on the airline and route. Major airlines operating here include Frontier Airlines, Delta, and JetBlue Airways.
  • Orlando Sanford International Airport (SFB): Found in Seminole County, Florida, around 13 miles from Winter Park, this airport primarily handles international flights, serving about 2 destinations worldwide. Arajet is a key airline providing service from this airport.

Top routes to Winter Park

  • New York (JFK/LGA) to Winter Park (MCO), with one-way flights starting at around $50
  • Newark (EWR) to Winter Park (MCO), with one-way airfare from around $65
  • Chicago (ORD/MDW) to Winter Park (MCO), with one-way airfare from around $45
  • Boston (BOS) to Winter Park (MCO), with one-way airfare from around $60
  • Washington (IAD/DCA) to Winter Park (MCO), with one-way flights starting at around $45

Cheapest routes to Winter Park

  • Pensacola (PNS) to Winter Park (MCO), with budget one-way fares from around $30
  • Atlanta (ATL) to Winter Park (MCO), with cheap one-way fares from around $30
  • Baltimore (BWI) to Winter Park (MCO), with budget one-way fares from around $35
  • Charlotte (CLT) to Winter Park (MCO), with affordable one-way prices from around $35
  • Fort Lauderdale (FLL) to Winter Park (MCO), with budget one-way fares from around $40

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Winter Park

  • American Airlines: Operating flights to Orlando International Airport (MCO), this airline represents about 23% of arrivals in Winter Park. Passengers can expect an average one-way fare of around $320, with options for business and first-class service depending on the route.
  • Delta: Also flying into Orlando International Airport (MCO), Delta accounts for roughly 17% of arrivals to Winter Park. The average one-way fare is about $320, offering various premium cabins, including premium economy, business, and first class based on the route.
  • Southwest Airlines: Serving Orlando International Airport (MCO), Southwest Airlines comprises nearly 17% of Winter Park arrivals. Travelers can anticipate an average one-way fare of approximately $220, making it a budget-friendly option.
  • Frontier Airlines: With flights to Orlando International Airport (MCO), Frontier Airlines is responsible for around 10% of arrivals in Winter Park. The average one-way fare is roughly $140, making it a cost-effective choice for many travelers.
  • JetBlue Airways: Flying into Orlando International Airport (MCO), JetBlue accounts for about 9% of arrivals to Winter Park. The average one-way fare is around $260, with available premium cabins including premium economy and business class, depending on the route.

Best time to fly to Winter Park

The most popular months for travelers to fly to Winter Park are February, March, and April, when peak temperatures in Winter Park can reach up to 72.5°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 80.2°F and typically the lowest average one-way fare (around $167), roughly 11% cheaper than the yearly average. Looking for additional cheaper months to fly? August, May, and October offer average one-way fares of around $178, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January60.3°F (15.7°C)Light RainMostly SunnyAverage$186
February64.0°F (17.8°C)Light RainMostly SunnyHigh$196
March67.5°F (19.7°C)Light RainMostly SunnyHigh$205
April72.5°F (22.5°C)Light RainMostly SunnyHigh$196
May77.0°F (25.0°C)Light RainMostly SunnyLow$178
June81.0°F (27.2°C)Light RainMostly SunnyAverage$193
July82.4°F (28.0°C)Light RainMostly SunnyAverage$182
August82.6°F (28.1°C)Moderate RainMostly SunnyAverage$177
September80.2°F (26.8°C)Light RainMostly SunnyLow$167
October75.0°F (23.9°C)Light RainMostly SunnyLow$180
November68.2°F (20.1°C)No Rain (Dry)Mostly SunnyAverage$189
December64.0°F (17.8°C)No Rain (Dry)Mostly SunnyAverage$213

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Winter Park

Getting some of the best deals on flights to Winter Park is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Winter Park hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Winter Park flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Winter Park

Winter Park welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Winter Park efficiently:

  • Public transportation: From Orlando International Airport, Brightline Orlando Station, a train station, is located about 1.9 miles away by car, while Sand Lake Road Station, a metro station, is situated about 5.7 miles away by car, providing convenient options for onward travel.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Winter Park, with options including free hotel shuttles and private rides, which can be arranged in advance.
  • Car rental: Renting a car in Winter Park is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Winter Park on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay in and around Winter Park

  • Orlando: As a vibrant metropolis, Orlando is a gateway to a multitude of attractions, making it an ideal destination for family vacations, entertainment seekers, and business travelers. Within the city, visitors can experience renowned venues such as the Walt Disney World® Resort, perfect for family fun, and the Orange County Convention Center, a hub for cultural events. Additionally, Orlando is home to beautiful beaches and theme parks, ensuring a diverse array of activities for every traveler. Situated in Orlando, Winter Park offers easy access to these exciting experiences.
  • Casselberry: Located 5 miles drive away from Winter Park, Casselberry is a charming city perfect for families and outdoor enthusiasts. With attractions such as Red Bug Lake Park, where visitors can enjoy nature and recreational activities, Casselberry is ideal for those seeking an urban park experience. The nearby Wekiwa Springs State Park offers stunning scenery and adventure, making it a popular choice for outdoor explorers. Education is also a key aspect here, with institutions like the University of Central Florida enhancing the local atmosphere.
  • Baldwin Park: Situated around the area of Winter Park, Baldwin Park is a delightful neighborhood that combines family-friendly activities with outdoor enjoyment. Visitors can explore the local shopping mall center or engage with educational institutions like Full Sail University, which has a rich history in the arts and entertainment sector. The Orlando Science Center provides engaging experiences for families, while Rollins College adds a touch of modern academia to the neighborhood. Baldwin Park's proximity to major attractions makes it a convenient stop for travelers.

Tips for short-haul flights to Winter Park

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, it’s often more economical to travel with just a carry-on. Optimize your packing by choosing mini toiletries, wearing your heaviest clothes, and coordinating outfits effectively. This way, you can also avoid the hassle of waiting at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may not provide in-flight entertainment. To keep yourself engaged, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it’s advisable to arrive at least 1.5 to 2 hours prior to departure, taking into account traffic and security checks.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Winter Park

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for long flights, choosing your seat is essential for comfort. Full-service airlines typically allow free seat selection once online check-in opens, which is usually 24–48 hours prior to your flight. Some airlines provide the option to select seats even earlier.
  • Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before your departure for international flights to accommodate check-in, security, and immigration procedures.
  • Relax at the airport—if you find yourself with extra time, take the opportunity to explore the shops, enjoy a coffee at a café, or unwind at your gate or in a departure lounge if you have access. Most airports offer free and accessible Wi-Fi.
  • Adjust to the new time zone mid-flight—begin to sync your body clock by setting your watch and adjusting your sleep schedule to align with your destination's time zone. Try to either sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Winter Park?
The cheapest month to fly to Winter Park is October when demand is low. Off-peak months are usually when you'll find cheap flights. To keep costs down, steer clear of flying during school breaks and public holidays.
Which US cities have the cheapest flights to Winter Park?
Get cheap flights to Winter Park from New York, Atlanta and Chicago. These cities generally offer the lowest fares to this much-loved destination. But keep in mind that seasonality, demand and stopovers will also impact rates, so stay flexible and book when prices are right.
Which US cities fly direct to Winter Park?
Take your pick of 79 US destinations providing direct flights to Winter Park. When reserving on Expedia, click on the "Direct flights only" box to compare nonstop routes. Fly to Winter Park from any of these major cities:
  • New York
  • Atlanta
  • Chicago
  • Dallas
  • Newark
How to find a cheap flight to Winter Park?
Book early for the best chance of scoring cheap flights to Winter Park. Also, consider traveling during off-peak months like January and February. If you jet off on a Thursday, you can save an average of 16% compared to those departing on a Sunday.* Save time searching every day and set up a price alert on the Expedia app. We'll let you know when fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Winter Park?
Although booking in advance is generally the easiest way to save cash, don't worry if your Winter Park trip is last minute. It's still possible to find cheap flights to Winter Park, especially if your plans have a little wiggle room. Try changing your trip dates, exploring different ticket options or jetting out of another airport.
How far in advance should I book a flight to Winter Park?
To pick up the biggest savings on domestic journeys, book your flight to Winter Park 28 days ahead of your travel dates. For international flights, it's two to four months in advance. This boosts your chances of securing your preferred departure dates and seats.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Winter Park?
You can generally find cheap flights to Winter Park on Sundays. Travelers can save about 8% on average compared to booking on a Friday, which is often the most expensive day to book.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Winter Park?
Winter Park is accessible from 128 airports globally through 35 carriers, with Orlando Intl. Airport (MCO) as its primary gateway. Take your pick of these popular airlines to Winter Park when organizing your journey:
  • Delta Air Lines
  • United Airlines
  • American Airlines
  • JetBlue Airways
Where do you fly into Winter Park?
When flying to Winter Park, the main airport to arrive at is Orlando Intl. Airport (MCO). You can also head to nearby hubs like Orlando Sanford Intl. Airport (SFB), Daytona Beach Intl. Airport (DAB) or Orlando Melbourne Intl. Airport (MLB). Another option to consider when you fly to Winter Park is Orlando Executive Airport (ORL).
How far is the airport from central Winter Park?
Arriving at Orlando Intl. Airport (MCO) puts you approximately 12 mi south of central Winter Park.
Can I save money by booking a Winter Park trip package?
Bundle your hotel and flight and you could save hundreds of dollars. What's more, you can add extras like activities and car rentals to your Winter Park flight and hotel package deal. With Expedia, it's simple to look after all your Winter Park travel arrangements in one place.
Can I change or cancel my flight to Winter Park?
If you booked your flight to Winter Park within the last 24 hours, you can often change or cancel it for free. After that, extra charges may apply depending on the airline's terms and conditions. For more information, head to our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be offered a credit for future flights instead of a direct refund. During your search on Expedia, select the "No cancel fee" or "Changes included" filters to find tickets with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

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

October 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 $76, while one-way tickets start from from $22. 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

Frontier Airlines, Allegiant Air, Breeze Airways, Southwest Airlines, American Airlines, Delta 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 Sanford Intl.
Destination airport IATA code
SFB
Destination city name
Orlando
Roundtrip price
$76

Trending flights to Winter Park

Prices were available within the past 7 days and start at $22 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Allegiant Air

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