
$36 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 $36 One Way, $66 Round Trip from Orlando to Winchester
Prices starting at $66 for return flights and $36 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

Sonesta Nashville Airport
Dec 4 - Dec 6
Orlando (MCO) to Nashville (BNA)
Reviewed on Aug 12, 2025

Hutton Hotel
Dec 4 - Dec 6
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
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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.