Flights from Chicago to York

Cheapest flights from Chicago

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.

Tue, Jul 22 - Wed, Aug 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$229 Roundtrip, found 6 days ago

$229

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $229 found 6 days ago

Tue, Jul 22 - Sun, Aug 10

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 6 days ago

$233

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Aug 10, priced at $233 found 6 days ago

Fri, Jul 18 - Wed, Aug 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$239 Roundtrip, found 6 days ago

$239

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 18 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $239 found 6 days ago

Fri, Jul 18 - Tue, Aug 12

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$249 Roundtrip, found 6 days ago

$249

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 18 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 12, priced at $249 found 6 days ago

Tue, Jul 22 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$263 Roundtrip, found 6 days ago

$263

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $263 found 6 days ago

Tue, Jul 22 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 6 days ago

$265

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Aug 9, priced at $265 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 6 days ago

$265

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $265 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$268 Roundtrip, found 6 days ago

$268

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $268 found 6 days ago

Wed, Jul 23 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$274 Roundtrip, found 6 days ago

$274

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jul 23 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Aug 9, priced at $274 found 6 days ago

Wed, Jul 23 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$278 Roundtrip, found 6 days ago

$278

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jul 23 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $278 found 6 days ago

Sat, Jul 19 - Wed, Aug 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 6 days ago

$279

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $279 found 6 days ago

Fri, Jul 18 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$284 Roundtrip, found 6 days ago

$284

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 18 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Aug 9, priced at $284 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$285 Roundtrip, found 6 days ago

$285

Roundtrip

found 6 days ago

Select Delta flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $285 found 6 days ago

Thu, Jul 24 - Wed, Aug 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$286 Roundtrip, found 6 days ago

$286

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Jul 24 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $286 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$290 Roundtrip, found 6 days ago

$290

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $290 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$293 Roundtrip, found 6 days ago

$293

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $293 found 6 days ago

Thu, Jul 24 - Tue, Aug 12

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$296 Roundtrip, found 6 days ago

$296

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Jul 24 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 12, priced at $296 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$300 Roundtrip, found 6 days ago

$300

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $300 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$303 Roundtrip, found 6 days ago

$303

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $303 found 6 days ago

Mon, Jul 21 - Mon, Aug 11

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$305 Roundtrip, found 6 days ago

$305

Roundtrip

found 6 days ago

Select United flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 11, priced at $305 found 6 days ago