Cheap flights To Winter Park (ORL) from $38

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Cheap Flights to Winter Park from $38 One Way, $69 Round Trip

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

Sun, Apr 19 - Fri, Apr 24
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Raleigh - Durham Intl. to Orlando Intl., returning Fri, Apr 24, priced at $69 found 4 days ago
Sat, May 9 - Sat, May 23
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$72 Roundtrip, found 5 days ago
$72
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Raleigh - Durham Intl. to Orlando Intl., returning Sat, May 23, priced at $72 found 5 days ago
Tue, Apr 28 - Fri, May 1
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$76 Roundtrip, found 8 hours ago
$76
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Raleigh - Durham Intl. to Orlando Intl., returning Fri, May 1, priced at $76 found 8 hours ago
Fri, May 29 - Thu, Jun 4
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$78 Roundtrip, found 1 hour ago
$78
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 29 from Raleigh - Durham Intl. to Orlando Intl., returning Thu, Jun 4, priced at $78 found 1 hour ago
Tue, Apr 28 - Fri, May 1
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$79 Roundtrip, found 8 hours ago
$79
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Raleigh - Durham Intl. to Orlando Intl., returning Fri, May 1, priced at $79 found 8 hours ago
Sat, May 9 - Wed, May 13
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$80 Roundtrip, found 21 hours ago
$80
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sat, May 9 from Raleigh - Durham Intl. to Orlando Intl., returning Wed, May 13, priced at $80 found 21 hours ago
Fri, May 29 - Thu, Jun 4
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$81 Roundtrip, found 1 hour ago
$81
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 29 from Raleigh - Durham Intl. to Orlando Intl., returning Thu, Jun 4, priced at $81 found 1 hour ago
Tue, May 5 - Tue, May 12
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 1 hour ago
$82
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Tue, May 5 from Raleigh - Durham Intl. to Orlando Intl., returning Tue, May 12, priced at $82 found 1 hour ago
Tue, Apr 14 - Tue, Apr 21
RDU
Raleigh - Durham Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 3 days ago
$82
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Raleigh - Durham Intl. to Orlando Intl., returning Tue, Apr 21, priced at $82 found 3 days ago
Sat, Apr 25 - Sat, May 2
LGA
LaGuardia
MCO
Orlando Intl.
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 25 from LaGuardia to Orlando Intl., returning Sat, May 2, priced at $92 just found

Winter Park Flight Information

Traveling To
Winter Park
Destination Airport IATA Code
ORL
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways
Flight Price
$69
Earliest Departing Flight
Latest Departing Flight

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Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

Apr 26 - Apr 30

4 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $518, price is now $277 per person
$277
per person
found 1 day ago
Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

Apr 28 - May 3

5 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,014, price is now $497 per person
$497
per person
found 1 day ago
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

Apr 26 - Apr 30

4 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $558, price is now $290 per person
$290
per person
found 1 day ago
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Winter Park premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Grand Seas MOD Collection by Sonesta
3.5-star property

Grand Seas MOD Collection by Sonesta

7.8/10 Good! (1,004 reviews)

May 10 - May 14

4 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • PremiumEconomy

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $826, price is now $675 per person
$675
per person
just found
Beautiful ocean view. Will stay again.

Reviewed on Mar 14, 2025

Boardwalk Inn and Suites
2.5-star property

Boardwalk Inn and Suites

8.4/10 Very Good! (1,709 reviews)

May 10 - May 14

4 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • PremiumEconomy

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $917, price is now $692 per person
$692
per person
just found
Absolutely fantastic.

Reviewed on Feb 9, 2026

Best Western Aku Tiki Inn
2.5-star property

Best Western Aku Tiki Inn

7.8/10 Good! (1,355 reviews)

May 10 - May 14

4 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • PremiumEconomy

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $1,059, price is now $848 per person
$848
per person
just found
Property maintenance is questionable, In Room air conditioner had an error on the thermostat and worked how it wanted to, the pool was cloudy the whole stay (4 days) and the Air Conditioning in the dining area did not work at all.

Reviewed on Aug 14, 2025

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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,510 reviews)

May 8 - May 11

3 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $1,140, price is now $923 per person
$923
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed. He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides. He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter. Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it. The water park is an extra fee FYI There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.

Reviewed on Apr 6, 2025

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (5,960 reviews)

May 8 - May 11

3 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $1,463, price is now $974 per person
$974
per person
found 1 day ago
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.

Reviewed on Feb 12, 2026

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,068 reviews)

May 8 - May 11

3 night stay

Chicago (ORD) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $2,086, price is now $1,642 per person
$1,642
per person
found 1 day ago
Great location for hospital access

Reviewed on Jul 8, 2025

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Winter Park

Save money on your flights to Winter Park as well as on hotel and car packages.

 

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Mix and Match

At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Winter Park flights air ticket. Save more on air travel every day in every way at Orbitz.

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 $69 and $92. If you were flying one-way from Raleigh (RDU), you could have nabbed fares from just $38.
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.