Cheap flights from Leesburg to Winchester from CA $656

View CA $656 flight on Mon, Aug. 18, 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 $656 for one-way flights and CA $1,117 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,117 Roundtrip, found 2 days ago
CA $1,117
Roundtrip
found 2 days ago
Select Aer Lingus flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,117 found 2 days ago
Aer Lingus
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,403 Roundtrip, found 2 days ago
CA $1,403
Roundtrip
found 2 days ago
Select Aer Lingus flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,403 found 2 days ago
Aer Lingus
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,410 Roundtrip, found 2 days ago
CA $1,410
Roundtrip
found 2 days ago
Select Aer Lingus flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,410 found 2 days ago
Aer Lingus
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,411 Roundtrip, found 2 days ago
CA $1,411
Roundtrip
found 2 days ago
Select Aer Lingus flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,411 found 2 days ago
American Airlines
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,436 Roundtrip, found 2 days ago
CA $1,436
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,436 found 2 days ago
Iberia
Mon, Aug. 18 - Wed, Sep. 3
MCO
Orlando
SOU
Southampton
CA $1,493 Roundtrip, found 2 days ago
CA $1,493
Roundtrip
found 2 days ago
Select Iberia flight, departing Mon, Aug. 18 from Orlando to Southampton, returning Wed, Sep. 3, priced at CA $1,493 found 2 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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