Flights from Chicago to Ocean Park

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 29 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 2 days ago

$243

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jul 29 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Aug 9, priced at $243 found 2 days ago

Fri, Jun 27 - Sat, Jul 5

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$250 Roundtrip, found 4 days ago

$250

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Jun 27 from Midway Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $250 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$254 Roundtrip, found 3 days ago

$254

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $254 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 3 days ago

$259

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $259 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 3 days ago

$259

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $259 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$260 Roundtrip, found 3 days ago

$260

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $260 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$263 Roundtrip, found 3 days ago

$263

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $263 found 3 days ago

Wed, Jul 30 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$270 Roundtrip, found 2 days ago

$270

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Aug 9, priced at $270 found 2 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$271 Roundtrip, found 3 days ago

$271

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $271 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$277 Roundtrip, found 3 days ago

$277

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $277 found 3 days ago

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 2 days ago

$279

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 5, priced at $279 found 2 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$284 Roundtrip, found 3 days ago

$284

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $284 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$289 Roundtrip, found 3 days ago

$289

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $289 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$290 Roundtrip, found 3 days ago

$290

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $290 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$291 Roundtrip, found 3 days ago

$291

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $291 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$295 Roundtrip, found 3 days ago

$295

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $295 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$298 Roundtrip, found 3 days ago

$298

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $298 found 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$299 Roundtrip, found 3 days ago

$299

Roundtrip

found 3 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $299 found 3 days ago

Tue, Jul 29 - Wed, Aug 6

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$301 Roundtrip, found 2 days ago

$301

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Aug 6, priced at $301 found 2 days ago

Thu, Jul 31 - Tue, Aug 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$303 Roundtrip, found 2 days ago

$303

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Jul 31 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 5, priced at $303 found 2 days ago