Flights from Chicago to Porter

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, Sep 12 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$183 Roundtrip, found 7 hours ago

$183

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Fri, Sep 12 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $183 found 7 hours ago

Mon, Sep 8 - Tue, Sep 16

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 Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $193 found 5 days ago

Mon, Sep 15 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$203 Roundtrip, found 7 hours ago

$203

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $203 found 7 hours ago

Sun, Sep 14 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$208 Roundtrip, found 7 hours ago

$208

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $208 found 7 hours ago

Mon, Sep 8 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 5 days ago

$210

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $210 found 5 days ago

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 2 days ago

$220

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jul 15 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $220 found 2 days ago

Sat, Sep 13 - Sat, Sep 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$222 Roundtrip, found 7 hours ago

$222

Roundtrip

found 7 hours ago

Select Frontier Airlines flight, departing Sat, Sep 13 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 20, priced at $222 found 7 hours ago

Sun, Sep 7 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $225 found 5 days ago

Mon, Sep 15 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$233 Roundtrip, found 7 hours ago

$233

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $233 found 7 hours ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 5 days ago

$237

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Thu, Sep 11 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 15, priced at $237 found 5 days ago

Mon, Sep 8 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 5 days ago

$243

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $243 found 5 days ago

Sun, Sep 14 - Mon, Sep 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 7 hours ago

$248

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $248 found 7 hours ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$248 Roundtrip, found 2 days ago

$248

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $248 found 2 days ago

Tue, Sep 16 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$251 Roundtrip, found 7 hours ago

$251

Roundtrip

found 7 hours ago

Select Delta flight, departing Tue, Sep 16 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $251 found 7 hours ago

Mon, Sep 15 - Sat, Sep 20

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 7 hours ago

$253

Roundtrip

found 7 hours ago

Select JetBlue Airways flight, departing Mon, Sep 15 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 20, priced at $253 found 7 hours ago

Sun, Sep 7 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$258 Roundtrip, found 5 days ago

$258

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $258 found 5 days ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 2 days ago

$259

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $259 found 2 days ago

Sun, Sep 14 - Wed, Sep 17

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$265 Roundtrip, found 7 hours ago

$265

Roundtrip

found 7 hours ago

Select Delta flight, departing Sun, Sep 14 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 17, priced at $265 found 7 hours ago

Wed, Jul 16 - Mon, Jul 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$269 Roundtrip, found 2 days ago

$269

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Jul 21, priced at $269 found 2 days ago

Wed, Sep 10 - Fri, Sep 19

MDW

Midway Intl.

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Portland Intl. Jetport

$279 Roundtrip, found 5 days ago

$279

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Sep 10 from Midway Intl. to Portland Intl. Jetport, returning Fri, Sep 19, priced at $279 found 5 days ago