Flights from Chicago to York Harbor

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.

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

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Portland Intl. Jetport

$288 Roundtrip, found 1 day ago

$288

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $288 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$293 Roundtrip, found 1 day ago

$293

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $293 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$322 Roundtrip, found 1 day ago

$322

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $322 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $323 found 1 day ago

Sat, Aug 9 - Fri, Aug 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$329 Roundtrip, found 1 day ago

$329

Roundtrip

found 1 day ago

Select United flight, departing Sat, Aug 9 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Aug 15, priced at $329 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$337 Roundtrip, found 1 day ago

$337

Roundtrip

found 1 day ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $337 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$338 Roundtrip, found 1 day ago

$338

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $338 found 1 day ago

Sat, Aug 9 - Thu, Aug 14

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$339 Roundtrip, found 1 day ago

$339

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Aug 9 from Midway Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $339 found 1 day ago

Fri, Aug 8 - Tue, Aug 12

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$339 Roundtrip, found 1 day ago

$339

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 12, priced at $339 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$342 Roundtrip, found 1 day ago

$342

Roundtrip

found 1 day ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $342 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$348 Roundtrip, found 1 day ago

$348

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $348 found 1 day ago

Fri, Aug 8 - Fri, Aug 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$350 Roundtrip, found 1 day ago

$350

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Aug 15, priced at $350 found 1 day ago

Wed, Aug 6 - Fri, Aug 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$353 Roundtrip, found 1 day ago

$353

Roundtrip

found 1 day ago

Select United flight, departing Wed, Aug 6 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Aug 15, priced at $353 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$357 Roundtrip, found 1 day ago

$357

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $357 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$363 Roundtrip, found 1 day ago

$363

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 8 from Midway Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $363 found 1 day ago

Wed, Aug 6 - Tue, Aug 12

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$363 Roundtrip, found 1 day ago

$363

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Aug 6 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 12, priced at $363 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$377 Roundtrip, found 1 day ago

$377

Roundtrip

found 1 day ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $377 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$384 Roundtrip, found 1 day ago

$384

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $384 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$387 Roundtrip, found 1 day ago

$387

Roundtrip

found 1 day ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $387 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$713 Roundtrip, found 1 day ago

$713

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $713 found 1 day ago