Cheap flights To Winter Park (ORL) from $108

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Cheap Flights to Winter Park from $108 One Way, $217 Round Trip

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

Thu, Nov 13 - Sun, Nov 16
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Punta Cana Intl. to Orlando Intl., returning Sun, Nov 16, priced at $217 found 2 hours ago
Fri, Nov 14 - Sun, Nov 16
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$226 Roundtrip, found 3 days ago
$226
Roundtrip
found 3 days ago
Select Arajet flight, departing Fri, Nov 14 from Punta Cana Intl. to Orlando Sanford Intl., returning Sun, Nov 16, priced at $226 found 3 days ago
Sat, Nov 15 - Thu, Nov 20
KIN
Norman Manley Intl.
MCO
Orlando Intl.
$291 Roundtrip, found 4 days ago
$291
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Norman Manley Intl. to Orlando Intl., returning Thu, Nov 20, priced at $291 found 4 days ago
Wed, Nov 26 - Sun, Nov 30
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$299 Roundtrip, found 13 hours ago
$299
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Wed, Nov 26 from Punta Cana Intl. to Orlando Intl., returning Sun, Nov 30, priced at $299 found 13 hours ago
Thu, Nov 20 - Sat, Dec 6
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$325 Roundtrip, found 2 days ago
$325
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 20 from Punta Cana Intl. to Orlando Intl., returning Sat, Dec 6, priced at $325 found 2 days ago
Thu, Nov 20 - Sat, Dec 6
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$326 Roundtrip, found 2 days ago
$326
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Nov 20 from Punta Cana Intl. to Orlando Intl., returning Sat, Dec 6, priced at $326 found 2 days ago
Fri, Nov 14 - Sun, Nov 16
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$335 Roundtrip, found 2 days ago
$335
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Nov 14 from Punta Cana Intl. to Orlando Intl., returning Sun, Nov 16, priced at $335 found 2 days ago
Tue, Dec 30 - Fri, Jan 16
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$349 Roundtrip, found 11 hours ago
$349
Roundtrip
found 11 hours ago
Select World Ticket Ltd flight, departing Tue, Dec 30 from Punta Cana Intl. to Orlando Sanford Intl., returning Fri, Jan 16, priced at $349 found 11 hours ago
Tue, Mar 17 - Tue, Mar 24
GRU
Guarulhos - Governor André Franco Montoro Intl.
SFB
Orlando Sanford Intl.
$370 Roundtrip, found 13 hours ago
$370
Roundtrip
found 13 hours ago
Select Arajet flight, departing Tue, Mar 17 from Guarulhos - Governor André Franco Montoro Intl. to Orlando Sanford Intl., returning Tue, Mar 24, priced at $370 found 13 hours ago
Wed, Nov 19 - Thu, Nov 20
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Select Copa flight, departing Wed, Nov 19 from Punta Cana Intl. to Orlando Intl., returning Thu, Nov 20, priced at $371 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, Frontier Airlines, JetBlue Airways, Delta, World Ticket Ltd, Hahn Air Technologies, American Airlines, Southwest Airlines, Copa
Flight Price
$217
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 7 - Dec 13

6 night stay

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach
Price was $982, price is now $298 per person
$298
per person
found 2 days ago
Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

Dec 11 - Dec 15

4 night stay

Boston (BOS) to Orlando (MCO)

Breeze Airways • Non-stop • Coach

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Non-stop • Coach
Price was $782, price is now $363 per person
$363
per person
found 1 day ago
Tropical Winds Oceanfront Hotel
2.5-star property

Tropical Winds Oceanfront Hotel

Dec 6 - Dec 14

8 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $752, price is now $409 per person
$409
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.
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 28 - Dec 31

3 night stay

Boston (BOS) to Orlando (MCO)

Delta • Roundtrip • PremiumEconomy
Price was $1,087, price is now $818 per person
$818
per person
found 1 day 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

Summerville Vacation Homes by Columbia Management
4.0-star property

Summerville Vacation Homes by Columbia Management

8.4/10 Very Good! (152 reviews)

Dec 22 - Dec 27

5 night stay

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

Delta • PremiumEconomy

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

Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $2,028, price is now $1,175 per person
$1,175
per person
found 10 hours ago
This concept is nicer than staying in a hotel room. The home was spacious and decorated very well. All necessities were provided. However, the ice maker in the refrigerator was not working. We were only there for 3 nights so I didn’t bother management with it.

Reviewed on Apr 19, 2021

Lake Buena Vista Resort Village & Spa
4.0-star property

Lake Buena Vista Resort Village & Spa

8.4/10 Very Good! (9,225 reviews)

Dec 21 - Dec 27

6 night stay

Chicago (ORD) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,584, price is now $1,170 per person
$1,170
per person
found 12 hours ago
This is our 3rd stay here. The best feature of the room is, the kitchen it comes equipped with everything you'll need. The laundry. A/C. The rooms need updating. Beds are comfy. Living area needs new furniture. Pool area with boat is the best part. Kids absolutely love it. Not deep. But there wasn't enough staff to keep the line moving or opened for the slide.

Reviewed on Sep 7, 2025

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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Orlando Airport
4.0-star property

DoubleTree by Hilton Orlando Airport

8.8/10 Excellent! (1,910 reviews)

Dec 11 - Dec 14

3 night stay

San Juan (SJU) to Orlando (MCO)

Delta • Non-stop • FirstClass

Orlando (MCO) to San Juan (SJU)

American Airlines • Non-stop • FirstClass
Price was $957, price is now $779 per person
$779
per person
found 1 day ago
Overall the property is good, but I use to work in a 5 star hotel before and I know good service and bad service. I just think maybe you guys need to train your staff members how provide better customer service. I had an issue your staff should always apologize to the customer on the company’s behalf. I didn’t get that from your staff. I telling my wife that I start up a company about teaching hospitality staff how to treat customers like they really matter.

Reviewed on Oct 11, 2025

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

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,395 reviews)

Dec 26 - Jan 1

6 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,167, price is now $1,579 per person
$1,579
per person
found 4 hours ago
It was ok for the price

Reviewed on Sep 27, 2025

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
3.0-star property

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

8/10 Very Good! (148 reviews)

Dec 26 - Jan 1

6 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,882, price is now $1,469 per person
$1,469
per person
found 4 hours ago
The staff were super nice especially the lady at the front desk and the lady around the cocktail area. The hotel was nice and clean with a nice view it was walkable to Icon park and restaurants. Will stay there again.

Reviewed on Jul 31, 2025

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Winter Park

If you are looking for affordable flights to Winter Park, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Winter Park now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Winter Park flights. With Orbitz, booking flights to Winter Park is easy and the lowest prices are guaranteed.

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Traveler profile updates

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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 $217 and $371. 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.