Flights from Winchester

Cheapest flights from Winchester

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$249 Roundtrip, found 12 hours ago

$249

Roundtrip

found 12 hours ago

Select American Airlines flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $249 found 12 hours ago

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$249 Roundtrip, found 12 hours ago

$249

Roundtrip

found 12 hours ago

Select United flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $249 found 12 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$259 Roundtrip, found 13 hours ago

$259

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $259 found 13 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$261 Roundtrip, found 13 hours ago

$261

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $261 found 13 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$264 Roundtrip, found 13 hours ago

$264

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $264 found 13 hours ago

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$269 Roundtrip, found 12 hours ago

$269

Roundtrip

found 12 hours ago

Select Delta flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $269 found 12 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$274 Roundtrip, found 13 hours ago

$274

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $274 found 13 hours ago

Fri, Sep 25 - Wed, Sep 30

LEX

Blue Grass

ORD

O'Hare Intl.

$279 Roundtrip, found 19 hours ago

$279

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Sep 30, priced at $279 found 19 hours ago

Sat, Jun 13 - Tue, Jun 23

LEX

Blue Grass

MCO

Orlando Intl.

$283 Roundtrip, found 2 days ago

$283

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Jun 13 from Blue Grass to Orlando Intl., returning Tue, Jun 23, priced at $283 found 2 days ago

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$284 Roundtrip, found 12 hours ago

$284

Roundtrip

found 12 hours ago

Select Delta flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $284 found 12 hours ago

Fri, Sep 25 - Wed, Sep 30

LEX

Blue Grass

ORD

O'Hare Intl.

$285 Roundtrip, found 19 hours ago

$285

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Sep 30, priced at $285 found 19 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$287 Roundtrip, found 13 hours ago

$287

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $287 found 13 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$289 Roundtrip, found 13 hours ago

$289

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $289 found 13 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$290 Roundtrip, found 13 hours ago

$290

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $290 found 13 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$291 Roundtrip, found 13 hours ago

$291

Roundtrip

found 13 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $291 found 13 hours ago

Sat, Jun 20 - Wed, Jul 1

LEX

Blue Grass

LAS

Harry Reid Intl.

$293 Roundtrip, found 5 days ago

$293

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Jun 20 from Blue Grass to Harry Reid Intl., returning Wed, Jul 1, priced at $293 found 5 days ago

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$294 Roundtrip, found 12 hours ago

$294

Roundtrip

found 12 hours ago

Select American Airlines flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $294 found 12 hours ago

Fri, Sep 25 - Wed, Oct 7

LEX

Blue Grass

ORD

O'Hare Intl.

$297 Roundtrip, found 13 hours ago

$297

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Oct 7, priced at $297 found 13 hours ago

Fri, Sep 25 - Wed, Sep 30

LEX

Blue Grass

ORD

O'Hare Intl.

$300 Roundtrip, found 19 hours ago

$300

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Sep 25 from Blue Grass to O'Hare Intl., returning Wed, Sep 30, priced at $300 found 19 hours ago

Thu, Sep 24 - Mon, Sep 28

LEX

Blue Grass

ORD

O'Hare Intl.

$304 Roundtrip, found 12 hours ago

$304

Roundtrip

found 12 hours ago

Select American Airlines flight, departing Thu, Sep 24 from Blue Grass to O'Hare Intl., returning Mon, Sep 28, priced at $304 found 12 hours ago