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, Sep 16 - Fri, Sep 26

ORD

O'Hare Intl.

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Portland Intl. Jetport

$210 Roundtrip, found 2 days ago

$210

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $210 found 2 days ago

Tue, Sep 16 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$223 Roundtrip, found 2 days ago

$223

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $223 found 2 days ago

Tue, Sep 16 - Tue, Sep 23

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$244 Roundtrip, found 2 days ago

$244

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 23, priced at $244 found 2 days ago

Tue, Sep 16 - Wed, Sep 24

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$261 Roundtrip, found 2 days ago

$261

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 24, priced at $261 found 2 days ago

Tue, Sep 16 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 2 days ago

$265

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $265 found 2 days ago

Mon, Sep 15 - Wed, Sep 24

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$270 Roundtrip, found 2 days ago

$270

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 24, priced at $270 found 2 days ago

Mon, Sep 15 - Thu, Sep 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 2 days ago

$279

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 25, priced at $279 found 2 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$286 Roundtrip, found 2 days ago

$286

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Sep 19 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $286 found 2 days ago

Wed, Sep 17 - Wed, Sep 24

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$288 Roundtrip, found 2 days ago

$288

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 24, priced at $288 found 2 days ago

Sun, Sep 14 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$292 Roundtrip, found 2 days ago

$292

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $292 found 2 days ago

Fri, Aug 22 - Thu, Oct 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$293 Roundtrip, found 4 days ago

$293

Roundtrip

found 4 days ago

Select American Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $293 found 4 days ago

Sat, Sep 20 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$297 Roundtrip, found 2 days ago

$297

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 20 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $297 found 2 days ago

Fri, Sep 19 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$299 Roundtrip, found 2 days ago

$299

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Sep 19 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $299 found 2 days ago

Sun, Sep 14 - Thu, Sep 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$303 Roundtrip, found 2 days ago

$303

Roundtrip

found 2 days ago

Select Delta flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Sep 25, priced at $303 found 2 days ago

Sun, Sep 14 - Sat, Sep 27

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$305 Roundtrip, found 2 days ago

$305

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $305 found 2 days ago

Fri, Aug 22 - Thu, Oct 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$307 Roundtrip, found 4 days ago

$307

Roundtrip

found 4 days ago

Select United flight, departing Fri, Aug 22 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $307 found 4 days ago

Wed, Sep 17 - Fri, Sep 26

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$315 Roundtrip, found 2 days ago

$315

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 17 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $315 found 2 days ago

Sat, Sep 20 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$327 Roundtrip, found 2 days ago

$327

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Sep 20 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $327 found 2 days ago

Sun, Sep 14 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$329 Roundtrip, found 2 days ago

$329

Roundtrip

found 2 days ago

Select United flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $329 found 2 days ago

Fri, Sep 19 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$347 Roundtrip, found 2 days ago

$347

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Sep 19 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $347 found 2 days ago