$30 Cheap flight deals from Orlando (ORL) to Winchester (CHA)
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This Weekend's Flight Deals from Orlando to Winchester
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.
Airfares from $30 One Way, $60 Round Trip from Orlando to Winchester
Prices starting at $60 for return flights and $30 for one-way flights to Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Winchester economy flight packages
Nashville Airport Marriott
Dec 26 - Dec 29
Orlando (MCO) to Nashville (BNA)
Reviewed on Oct 26, 2025
Hutton Hotel
Dec 26 - Dec 29
Orlando (MCO) to Nashville (BNA)
Reviewed on Jul 31, 2025
More About Flying To Winchester from Orlando
Route Information for Flights from Orlando to Winchester
Origin Airport IATA Code | ORL |
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Destination Airport IATA Code | CHA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Orlando to Winchester
Orbitz is the number one travel site for finding guaranteed low prices on Orlando to Winchester flights. Not only do we have discount tickets on domestic and international tickets but our cutting-edge mobile tools keep you informed on the go.
Find Low Prices in One Place
Booking a trip from Orlando to Winchester has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Winchester to your flight or hotel reservation to keep the kids happy and active.
Flight Booking, Alerts, and More on Your Mobile Device
Use our mobile app for your iPhone, iPad, or Android phone—or our mobile website m.orbitz.com—to find bargains on flights from Orlando to Winchester wherever you are. Book your cheap Orlando to Winchester flights and a hotel room too—even at the last minute. Orbitz also makes your life easier with free alerts that are sent to your mobile phone or email about delays to your upcoming flights from Orlando to Winchester.
Don’t Miss out on Miles
Accumulate frequent flyer miles or points on your Orlando to Winchester flights. It’s as simple as entering your frequent flyer number when you’re making your flight reservation on Orbitz to rack up miles on qualified flights from Orlando to Winchester. You can save your frequent flyer numbers in your Orbitz account to save time during your next flight booking.
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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.