$40 Cheap flight deals from Pittsburgh (PIT) to Winter Park (ORL)

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This Weekend's Flight Deals from Pittsburgh to Winter Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jul 26 - Sat, Aug 30
LBE
Arnold Palmer Regional
MCO
Orlando Intl.
$170 Roundtrip, found 19 hours ago
$170
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sat, Jul 26 from Arnold Palmer Regional to Orlando Intl., returning Sat, Aug 30, priced at $170 found 19 hours ago
Sat, Jul 26 - Mon, Jul 28
PIT
Pittsburgh Intl.
MCO
Orlando Intl.
$274 Roundtrip, found 6 hours ago
$274
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sat, Jul 26 from Pittsburgh Intl. to Orlando Intl., returning Mon, Jul 28, priced at $274 found 6 hours ago

Airfares from $40 One Way, $80 Round Trip from Pittsburgh to Winter Park

Prices starting at $80 for return flights and $40 for one-way flights to Winter Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 25 - Tue, Mar 3
PIT
Pittsburgh
MCO
Orlando
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Feb 25 from Pittsburgh to Orlando, returning Tue, Mar 3, priced at $80 just found
Fri, Sep 26 - Tue, Sep 30
PIT
Pittsburgh
MCO
Orlando
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 26 from Pittsburgh to Orlando, returning Tue, Sep 30, priced at $82 just found
Sun, Oct 19 - Fri, Oct 24
PIT
Pittsburgh
MCO
Orlando
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sun, Oct 19 from Pittsburgh to Orlando, returning Fri, Oct 24, priced at $82 found 9 hours ago
Sat, Dec 6 - Sat, Dec 13
LBE
Latrobe
MCO
Orlando
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Dec 6 from Latrobe to Orlando, returning Sat, Dec 13, priced at $90 just found
Fri, Sep 12 - Mon, Sep 15
PIT
Pittsburgh
MCO
Orlando
$166 Roundtrip, found 10 hours ago
$166
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Fri, Sep 12 from Pittsburgh to Orlando, returning Mon, Sep 15, priced at $166 found 10 hours ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (995 reviews)

Aug 30 - Sep 4

5 night stay

Pittsburgh (PIT) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
Originally got a one bedroom villa and got a free upgrade to a two bedroom which was perfect. The villa was super clean, easy access, washer/dryer, kitchen fully stored with pots, pans, utensils, cups, and plates. They had enough towels for our entire stay, and even had beach towels as well. They had everything that you needed. I didn’t need to call the front desk for anything my entire stay. I loved that place and the size of the villa was perfect for the two of us and maybe more. Definitely will come back if I’m ever back in Orlando.

Reviewed on Jun 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! (5,097 reviews)

Aug 24 - Aug 30

6 night stay

Pittsburgh (PIT) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Pittsburgh (PIT)

Spirit Airlines • Coach
per person
found 1 day ago
Pros: Clean, beautiful grounds. There are pools throughout the property, and food/store options available onsite. Beds were comfortable. Nice patios. Able to get bus to Universal for free. Cons: Check in was awful. Took close to 1 hour. There is a shuttle that can take you from your building to the front as it's a long walk. However, we mostly had to walk because the shuttle was either parked up front or MIA. The property and rooms are dated. Plugs/outlets in the room were few and we had two just not even work in our room. The waterpark was fine, but requires additional paid entry for non-members. Pools on property are just open swimming..no attendants.

Reviewed on Jun 23, 2025

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.6/10 Excellent! (1,006 reviews)

Aug 29 - Sep 4

6 night stay

Pittsburgh (PIT) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Pittsburgh (PIT)

Spirit Airlines • Coach
per person
found 1 day ago
Only thing that we complained was bed sheets were dirty and floor in one of the room full of hair.

Reviewed on Jul 3, 2025

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More About Flying To Winter Park from Pittsburgh

Route Information for Flights from Pittsburgh to Winter Park

Origin Airport IATA Code
PIT
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Pittsburgh to Winter Park

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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.