Cheap flights To Winter Park (ORL) from $29

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Cheap Flights to Winter Park from $29 One Way, $64 Round Trip

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

Wed, May 20 - Thu, May 21
ORD
O'Hare Intl.
MCO
Orlando Intl.
$64 Roundtrip, found 10 hours ago
$64
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, May 20 from O'Hare Intl. to Orlando Intl., returning Thu, May 21, priced at $64 found 10 hours ago
Tue, May 12 - Thu, May 21
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, May 12 from Newark Liberty Intl. Airport to Orlando Intl., returning Thu, May 21, priced at $74 found 2 days ago
Fri, May 29 - Sat, May 30
ORD
O'Hare Intl.
MCO
Orlando Intl.
$80 Roundtrip, found 22 hours ago
$80
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, May 29 from O'Hare Intl. to Orlando Intl., returning Sat, May 30, priced at $80 found 22 hours ago
Thu, Jun 4 - Sun, Jun 7
TTN
Mercer
MCO
Orlando Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Jun 4 from Mercer to Orlando Intl., returning Sun, Jun 7, priced at $80 found 1 hour ago
Fri, May 29 - Thu, Jun 4
TTN
Mercer
MCO
Orlando Intl.
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 29 from Mercer to Orlando Intl., returning Thu, Jun 4, priced at $82 just found
Fri, May 29 - Tue, Jun 2
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$85 Roundtrip, just found
$85
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 29 from Newark Liberty Intl. Airport to Orlando Intl., returning Tue, Jun 2, priced at $85 just found
Tue, Sep 1 - Wed, Sep 2
ORD
O'Hare Intl.
MCO
Orlando Intl.
$86 Roundtrip, found 2 days ago
$86
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 1 from O'Hare Intl. to Orlando Intl., returning Wed, Sep 2, priced at $86 found 2 days ago
Tue, May 26 - Wed, Jun 3
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 26 from Newark Liberty Intl. Airport to Orlando Intl., returning Wed, Jun 3, priced at $88 found 1 day ago
Tue, Jul 7 - Mon, Jul 13
LGA
LaGuardia
MCO
Orlando Intl.
$88 Roundtrip, found 4 hours ago
$88
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jul 7 from LaGuardia to Orlando Intl., returning Mon, Jul 13, priced at $88 found 4 hours ago
Fri, May 29 - Sat, May 30
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$89 Roundtrip, found 11 hours ago
$89
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, May 29 from Newark Liberty Intl. Airport to Orlando Intl., returning Sat, May 30, priced at $89 found 11 hours ago

Winter Park Flight Information

Traveling To
Winter Park
Destination Airport IATA Code
ORL
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines
Flight Price
$64
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.
Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

Jun 6 - Jun 13

7 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $823, price is now $373 per person
$373
per person
found 1 day ago
Harbor Island Beach Club by Villatel
2.0-star property

Harbor Island Beach Club by Villatel

Jun 24 - Jun 30

6 night stay

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

American Airlines • Non-stop roundtrip • Coach
Price was $2,996, price is now $1,507 per person
$1,507
per person
found 5 hours ago
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

Jun 14 - Jun 20

6 night stay

Boston (BOS) to Orlando (MCO)

Delta • Coach

Orlando (MCO) to Boston (BOS)

Breeze Airways • Coach
Save 100% on your flight
Price was $1,279, price is now $722 per person
$722
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Winter Park
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Winter Park premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Orlando Resort Bonnet Creek
4.0-star property

Wyndham Grand Orlando Resort Bonnet Creek

9/10 Wonderful! (2,923 reviews)

Jun 1 - Jun 6

5 night stay

New York (NYC) to Orlando (MCO)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $788, price is now $633 per person
$633
per person
found 1 day ago
Clean, spacious room. Comfortable bed. Attractive lobby and restaurants. Property attractive

Reviewed on Mar 27, 2026

Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,134 reviews)

Jun 5 - Jun 7

2 night stay

New York (JFK) to Orlando (MCO)

Frontier Airlines • Non-stop • PremiumEconomy

Orlando (MCO) to New York (JFK)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $810, price is now $675 per person
$675
per person
found 3 hours ago
Clean room, Friendly Staff, the breakfast menu was fresh every day! Everything was great!

Reviewed on Apr 28, 2026

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens
4.0-star property

Riviere 3BR Apartment Stylish King Family Pets Friendly Pool & Gym Near Epic UniverseOpens

No reviews

Jun 5 - Jun 7

2 night stay

New York (JFK) to Orlando (MCO)

Frontier Airlines • Non-stop • PremiumEconomy

Orlando (MCO) to New York (JFK)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $1,048, price is now $885 per person
$885
per person
found 2 hours ago
Don't see what you're looking for?
See all available trips from New York to Winter Park
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Winter Park business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,092 reviews)

Jun 19 - Jun 22

3 night stay

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

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,038, price is now $853 per person
$853
per person
found 9 hours ago
Great location for hospital access

Reviewed on Jul 8, 2025

Margaritaville Cottages Orlando by Vstays with H2O Waterpark
4.0-star property

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

9.2/10 Wonderful! (1,009 reviews)

Jun 19 - Jun 22

3 night stay

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

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,402, price is now $1,075 per person
$1,075
per person
found 9 hours ago
This place is amazing! I just wish we had more time to enjoy the resort.

Reviewed on Apr 1, 2026

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
5.0-star property

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

9.2/10 Wonderful! (500 reviews)

Jun 19 - Jun 22

3 night stay

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

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,334, price is now $1,122 per person
$1,122
per person
found 9 hours ago
Few options for dining , not too much activities for a family with kids . Otherwise nice place to stay for those looking a good , quiet , and highly friendly environment.

Reviewed on Jan 10, 2025

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Winter Park

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Low Prices for Winter Park Flights

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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 $64 and $89. If you were flying one-way from Chicago (ORD), you could have nabbed fares from just $29.
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.