Flights from Chicago to Portland

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 23 - Wed, Sep 24

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$278 Roundtrip, found 1 day ago

$278

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Portland Intl. Jetport, returning Wed, Sep 24, priced at $278 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$288 Roundtrip, found 5 days ago

$288

Roundtrip

found 5 days 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 5 days ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$293 Roundtrip, found 5 days ago

$293

Roundtrip

found 5 days 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 5 days ago

Tue, Sep 23 - Fri, Sep 26

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$299 Roundtrip, found 1 day ago

$299

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $299 found 1 day ago

Sat, Sep 20 - Tue, Sep 23

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$311 Roundtrip, found 1 day ago

$311

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 20 from Midway Intl. to Portland Intl. Jetport, returning Tue, Sep 23, priced at $311 found 1 day ago

Sun, Sep 21 - Tue, Sep 23

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$314 Roundtrip, found 1 day ago

$314

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Sep 21 from Midway Intl. to Portland Intl. Jetport, returning Tue, Sep 23, priced at $314 found 1 day ago

Tue, Sep 23 - Sat, Sep 27

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$319 Roundtrip, found 1 day ago

$319

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $319 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$322 Roundtrip, found 5 days ago

$322

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $322 found 5 days ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$323 Roundtrip, found 5 days ago

$323

Roundtrip

found 5 days 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 5 days ago

Sat, Aug 9 - Fri, Aug 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$329 Roundtrip, found 5 days ago

$329

Roundtrip

found 5 days ago

Select United flight, departing Sat, Aug 9 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Aug 15, priced at $329 found 5 days ago

Sat, Sep 20 - Fri, Sep 26

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$332 Roundtrip, found 1 day ago

$332

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 20 from Midway Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $332 found 1 day ago

Sun, Sep 21 - Fri, Sep 26

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$335 Roundtrip, found 1 day ago

$335

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Sep 21 from Midway Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $335 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$337 Roundtrip, found 5 days ago

$337

Roundtrip

found 5 days ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $337 found 5 days ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$338 Roundtrip, found 5 days ago

$338

Roundtrip

found 5 days 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 5 days ago

Fri, Aug 8 - Tue, Aug 12

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$339 Roundtrip, found 5 days ago

$339

Roundtrip

found 5 days 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 5 days ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$342 Roundtrip, found 5 days ago

$342

Roundtrip

found 5 days ago

Select United flight, departing Fri, Aug 8 from O'Hare Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $342 found 5 days ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$348 Roundtrip, found 5 days ago

$348

Roundtrip

found 5 days 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 5 days ago

Fri, Aug 8 - Fri, Aug 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$350 Roundtrip, found 5 days ago

$350

Roundtrip

found 5 days 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 5 days ago

Sat, Sep 20 - Sat, Sep 27

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$352 Roundtrip, found 1 day ago

$352

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 20 from Midway Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $352 found 1 day ago

Fri, Aug 8 - Thu, Aug 14

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$713 Roundtrip, found 5 days ago

$713

Roundtrip

found 5 days 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 5 days ago