Cheap flights from Leesburg to Winchester from CA $784

View CA $784 flight on Sun, Aug. 17, 2025Opens in a new window

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Cheap flights from Leesburg (ORL) to Winchester (SOU)

Prices were available within the past 7 days and start at CA $784 for one-way flights and CA $1,081 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,081 Roundtrip, found 5 days ago
CA $1,081
Roundtrip
found 5 days ago
Select Aer Lingus flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,081 found 5 days ago
Aer Lingus
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,372 Roundtrip, found 5 days ago
CA $1,372
Roundtrip
found 5 days ago
Select Aer Lingus flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,372 found 5 days ago
Virgin Atlantic
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,379 Roundtrip, found 5 days ago
CA $1,379
Roundtrip
found 5 days ago
Select Virgin Atlantic flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,379 found 5 days ago
American Airlines
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,434 Roundtrip, found 5 days ago
CA $1,434
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,434 found 5 days ago
Delta
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,448 Roundtrip, found 5 days ago
CA $1,448
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,448 found 5 days ago
Iberia
Sun, Aug. 17 - Tue, Aug. 26
MCO
Orlando
SOU
Southampton
CA $1,505 Roundtrip, found 5 days ago
CA $1,505
Roundtrip
found 5 days ago
Select Iberia flight, departing Sun, Aug. 17 from Orlando to Southampton, returning Tue, Aug. 26, priced at CA $1,505 found 5 days ago

Find the cheapest month to fly from Orlando (MCO) to Southampton (SOU)

March is typically the cheapest month to fly

From CA $1,042 - CA $2,027 per traveller.

Graph displaying average flight prices per month

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