Cheap flights To Winter Park (ORL) from $106

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Cheap Flights to Winter Park from $106 One Way, $202 Round Trip

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

Sat, May 2 - Sat, May 9
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from Punta Cana Intl. to Orlando Intl., returning Sat, May 9, priced at $202 found 1 day ago
Tue, Mar 17 - Fri, Mar 20
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Arajet flight, departing Tue, Mar 17 from Punta Cana Intl. to Orlando Sanford Intl., returning Fri, Mar 20, priced at $206 found 1 day ago
Thu, Mar 5 - Wed, Mar 11
LIM
Jorge Chávez Intl.
MCO
Orlando Intl.
$210 Roundtrip, found 7 hours ago
$210
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Thu, Mar 5 from Jorge Chávez Intl. to Orlando Intl., returning Wed, Mar 11, priced at $210 found 7 hours ago
Thu, Feb 12 - Sun, Feb 15
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$288 Roundtrip, found 7 hours ago
$288
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Thu, Feb 12 from Punta Cana Intl. to Orlando Intl., returning Sun, Feb 15, priced at $288 found 7 hours ago
Sun, Jul 26 - Fri, Aug 14
PUJ
Punta Cana Intl.
SFB
Orlando Sanford Intl.
$303 Roundtrip, found 13 hours ago
$303
Roundtrip
found 13 hours ago
Select World Ticket Ltd flight, departing Sun, Jul 26 from Punta Cana Intl. to Orlando Sanford Intl., returning Fri, Aug 14, priced at $303 found 13 hours ago
Wed, Mar 25 - Tue, Apr 7
KIN
Norman Manley Intl.
MCO
Orlando Intl.
$308 Roundtrip, found 22 hours ago
$308
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Wed, Mar 25 from Norman Manley Intl. to Orlando Intl., returning Tue, Apr 7, priced at $308 found 22 hours ago
Sat, Feb 7 - Mon, Feb 9
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$335 Roundtrip, found 7 hours ago
$335
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Punta Cana Intl. to Orlando Intl., returning Mon, Feb 9, priced at $335 found 7 hours ago
Sat, Feb 7 - Mon, Feb 9
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$338 Roundtrip, found 7 hours ago
$338
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Feb 7 from Punta Cana Intl. to Orlando Intl., returning Mon, Feb 9, priced at $338 found 7 hours ago
Sat, Feb 7 - Mon, Feb 9
PUJ
Punta Cana Intl.
MCO
Orlando Intl.
$338 Roundtrip, found 7 hours ago
$338
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Feb 7 from Punta Cana Intl. to Orlando Intl., returning Mon, Feb 9, priced at $338 found 7 hours ago
Fri, Feb 27 - Sun, May 24
GRU
Guarulhos - Governor André Franco Montoro Intl.
SFB
Orlando Sanford Intl.
$356 Roundtrip, found 7 hours ago
$356
Roundtrip
found 7 hours ago
Select Arajet flight, departing Fri, Feb 27 from Guarulhos - Governor André Franco Montoro Intl. to Orlando Sanford Intl., returning Sun, May 24, priced at $356 found 7 hours ago

Winter Park Flight Information

Traveling To
Winter Park
Destination Airport IATA Code
ORL
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Arajet, Southwest Airlines, JetBlue Airways, World Ticket Ltd, Delta, American Airlines
Flight Price
$202
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

Mar 2 - Mar 6

4 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • Coach

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach
Price was $830, price is now $272 per person
$272
per person
found 1 day ago
Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

Mar 14 - Mar 19

5 night stay

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

Spirit Airlines • Roundtrip • Coach
Price was $2,427, price is now $1,077 per person
$1,077
per person
found 21 hours ago
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

Mar 26 - Mar 31

5 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $843, price is now $386 per person
$386
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.
The Grove Resort & Water Park Orlando
4.0-star property

The Grove Resort & Water Park Orlando

8/10 Very Good! (8,735 reviews)

Mar 15 - Mar 19

4 night stay

Philadelphia (PHL) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Philadelphia (PHL)

JetBlue Airways • PremiumEconomy
Price was $1,154, price is now $643 per person
$643
per person
found 9 hours ago
The room was fantastic and we enjoyed the pool area. The woman who checked us in was not friendly though.

Reviewed on Jan 7, 2026

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

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 11 - Mar 14

3 night stay

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

Frontier Airlines • PremiumEconomy

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

Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,009, price is now $730 per person
$730
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (2,232 reviews)

Mar 15 - Mar 19

4 night stay

Philadelphia (PHL) to Orlando (MCO)

Spirit Airlines • PremiumEconomy

Orlando (MCO) to Philadelphia (PHL)

JetBlue Airways • PremiumEconomy
Price was $978, price is now $704 per person
$704
per person
found 9 hours ago
What a stunning and beautiful hotel. My son loved it also and having full access to the mall was a bonus!! Will definitely be back soon!

Reviewed on Dec 9, 2025

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Winter Park first class 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! (2,232 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (ORD) to Orlando (MCO)

United • FirstClass

Orlando (MCO) to Chicago (ORD)

American Airlines • FirstClass
Price was $1,989, price is now $1,493 per person
$1,493
per person
found 22 hours ago
What a stunning and beautiful hotel. My son loved it also and having full access to the mall was a bonus!! Will definitely be back soon!

Reviewed on Dec 9, 2025

The Grove Resort & Water Park Orlando
4.0-star property

The Grove Resort & Water Park Orlando

8/10 Very Good! (8,735 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (ORD) to Orlando (MCO)

United • FirstClass

Orlando (MCO) to Chicago (ORD)

American Airlines • FirstClass
Price was $2,445, price is now $1,613 per person
$1,613
per person
found 22 hours ago
The room was fantastic and we enjoyed the pool area. The woman who checked us in was not friendly though.

Reviewed on Jan 7, 2026

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

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9.2/10 Wonderful! (1,001 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (ORD) to Orlando (MCO)

United • FirstClass

Orlando (MCO) to Chicago (ORD)

American Airlines • FirstClass
Price was $2,686, price is now $1,950 per person
$1,950
per person
found 22 hours ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

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See all available trips from Chicago to Winter Park
View all trips

Winter Park

Traveling to Winter Park and need a cheap flight? Orbitz has great deals on flights to Winter Park right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

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Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Winter Park or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Winter Park flights. When you need us, we’re here for you!

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 $202 and $356. If you were flying one-way from Punta Cana (PUJ), you could have nabbed fares from just $106.
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.