Flights from Chicago to South Coast

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, Jul 23

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$203 Roundtrip, found 6 days ago

$203

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $203 found 6 days ago

Tue, Jul 22 - Fri, Jul 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 6 days ago

$210

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 25, priced at $210 found 6 days ago

Tue, Jul 29 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 19 hours ago

$243

Roundtrip

found 19 hours 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 19 hours ago

Fri, Jun 27 - Sat, Jul 5

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$250 Roundtrip, found 2 days ago

$250

Roundtrip

found 2 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 2 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day 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 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 1 day ago

$259

Roundtrip

found 1 day 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 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 1 day ago

$259

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $259 found 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$260 Roundtrip, found 1 day ago

$260

Roundtrip

found 1 day 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 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$263 Roundtrip, found 1 day ago

$263

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $263 found 1 day ago

Fri, Jul 18 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$269 Roundtrip, found 6 days ago

$269

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Fri, Jul 18 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $269 found 6 days ago

Wed, Jul 30 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$270 Roundtrip, found 19 hours ago

$270

Roundtrip

found 19 hours 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 19 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$271 Roundtrip, found 1 day ago

$271

Roundtrip

found 1 day 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 1 day ago

Mon, Jul 21 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$273 Roundtrip, found 6 days ago

$273

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $273 found 6 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$277 Roundtrip, found 1 day ago

$277

Roundtrip

found 1 day 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 1 day ago

Thu, Jul 17 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$278 Roundtrip, found 6 days ago

$278

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Jul 17 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $278 found 6 days ago

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 19 hours ago

$279

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 5, priced at $279 found 19 hours ago

Sat, Jul 19 - Fri, Jul 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$280 Roundtrip, found 6 days ago

$280

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 25, priced at $280 found 6 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$284 Roundtrip, found 1 day ago

$284

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $284 found 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$289 Roundtrip, found 1 day ago

$289

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $289 found 1 day ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$290 Roundtrip, found 1 day ago

$290

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $290 found 1 day ago