Flights from Chicago to Orrs Island

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, Jun 27 - Sat, Jul 5

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Fri, Jun 27 from Midway Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $254 found 1 day ago

Mon, Jun 23 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$310 Roundtrip, found 1 day ago

$310

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jun 23 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $310 found 1 day ago

Tue, Jun 24 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$340 Roundtrip, found 1 day ago

$340

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $340 found 1 day ago

Mon, Jun 23 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$350 Roundtrip, found 1 day ago

$350

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jun 23 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $350 found 1 day ago

Tue, Jun 24 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$380 Roundtrip, found 1 day ago

$380

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $380 found 1 day ago

Sat, Jun 21 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$417 Roundtrip, found 1 day ago

$417

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 21 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $417 found 1 day ago

Wed, Jun 25 - Fri, Jul 4

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$421 Roundtrip, found 1 day ago

$421

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jun 25 from Midway Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $421 found 1 day ago

Sat, Jun 28 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$429 Roundtrip, found 1 day ago

$429

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 28 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $429 found 1 day ago

Thu, Jun 26 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$437 Roundtrip, found 1 day ago

$437

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Jun 26 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $437 found 1 day ago

Tue, Jun 24 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$450 Roundtrip, found 1 day ago

$450

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $450 found 1 day ago

Tue, Jun 24 - Mon, Jun 30

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$451 Roundtrip, found 1 day ago

$451

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Portland Intl. Jetport, returning Mon, Jun 30, priced at $451 found 1 day ago

Sat, Jun 21 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$457 Roundtrip, found 1 day ago

$457

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 21 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $457 found 1 day ago

Wed, Jun 25 - Fri, Jul 4

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$465 Roundtrip, found 1 day ago

$465

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jun 25 from Midway Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $465 found 1 day ago

Sat, Jun 28 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$469 Roundtrip, found 1 day ago

$469

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 28 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $469 found 1 day ago

Thu, Jun 26 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$477 Roundtrip, found 1 day ago

$477

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Jun 26 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $477 found 1 day ago

Sun, Jun 22 - Wed, Jul 2

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$479 Roundtrip, found 1 day ago

$479

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Jun 22 from Midway Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $479 found 1 day ago

Wed, Jun 25 - Fri, Jul 4

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$490 Roundtrip, found 1 day ago

$490

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jun 25 from Midway Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $490 found 1 day ago

Sun, Jun 22 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$519 Roundtrip, found 1 day ago

$519

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Jun 22 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $519 found 1 day ago

Tue, Jun 24 - Thu, Jul 3

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$520 Roundtrip, found 1 day ago

$520

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $520 found 1 day ago

Sat, Jun 21 - Mon, Jun 30

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$528 Roundtrip, found 1 day ago

$528

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 21 from Midway Intl. to Portland Intl. Jetport, returning Mon, Jun 30, priced at $528 found 1 day ago