Flights from Chicago to Parsonsfield

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, May 13 - Tue, May 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$182 Roundtrip, found 5 days ago

$182

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, May 13 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, May 20, priced at $182 found 5 days ago

Sat, Jun 14 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$183 Roundtrip, found 4 days ago

$183

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Jun 14 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $183 found 4 days ago

Sat, Jun 7 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$192 Roundtrip, found 4 days ago

$192

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Jun 7 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $192 found 4 days ago

Tue, May 13 - Wed, May 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 5 days ago

$193

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Tue, May 13 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, May 21, priced at $193 found 5 days ago

Fri, Jun 13 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$198 Roundtrip, found 5 days ago

$198

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Fri, Jun 13 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $198 found 5 days ago

Sat, Jun 7 - Tue, Jun 17

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$201 Roundtrip, found 4 days ago

$201

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Jun 7 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jun 17, priced at $201 found 4 days ago

Sun, Jun 15 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$202 Roundtrip, found 5 days ago

$202

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sun, Jun 15 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $202 found 5 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$205 Roundtrip, found 5 days ago

$205

Roundtrip

found 5 days ago

Select American Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $205 found 5 days ago

Sat, May 17 - Tue, May 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$207 Roundtrip, found 5 days ago

$207

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sat, May 17 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, May 20, priced at $207 found 5 days ago

Mon, Jun 30 - Sat, Jul 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$209 Roundtrip, found 2 days ago

$209

Roundtrip

found 2 days ago

Select United flight, departing Mon, Jun 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $209 found 2 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$215 Roundtrip, found 5 days ago

$215

Roundtrip

found 5 days ago

Select Delta flight, departing Thu, Jun 12 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $215 found 5 days ago

Tue, Jul 1 - Wed, Jul 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$217 Roundtrip, found 2 days ago

$217

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $217 found 2 days ago

Sat, May 17 - Wed, May 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$218 Roundtrip, found 5 days ago

$218

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sat, May 17 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, May 21, priced at $218 found 5 days ago

Sun, May 11 - Sat, May 17

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$218 Roundtrip, found 5 days ago

$218

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, May 11 from Midway Intl. to Portland Intl. Jetport, returning Sat, May 17, priced at $218 found 5 days ago

Mon, Jun 30 - Sat, Jul 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$219 Roundtrip, found 2 days ago

$219

Roundtrip

found 2 days ago

Select United flight, departing Mon, Jun 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $219 found 2 days ago

Sun, May 11 - Sun, May 18

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, May 11 from Midway Intl. to Portland Intl. Jetport, returning Sun, May 18, priced at $220 found 5 days ago

Fri, Jun 27 - Wed, Jul 2

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$223 Roundtrip, found 2 days ago

$223

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jun 27 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Jul 2, priced at $223 found 2 days ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select Delta flight, departing Thu, Jun 12 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jun 16, priced at $225 found 5 days ago

Sun, May 11 - Thu, May 15

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$228 Roundtrip, found 5 days ago

$228

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, May 11 from Midway Intl. to Portland Intl. Jetport, returning Thu, May 15, priced at $228 found 5 days ago

Mon, Jun 30 - Sat, Jul 5

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$255 Roundtrip, found 2 days ago

$255

Roundtrip

found 2 days ago

Select American Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $255 found 2 days ago