Flights from Chicago to Biddeford

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.

Mon, Sep 8 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$193 Roundtrip, found 2 hours ago

$193

Roundtrip

found 2 hours 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 2 hours ago

Sun, Sep 7 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$208 Roundtrip, found 2 hours ago

$208

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $208 found 2 hours ago

Mon, Sep 8 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 2 hours ago

$210

Roundtrip

found 2 hours 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 2 hours ago

Thu, Sep 11 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 2 hours ago

$220

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Thu, Sep 11 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $220 found 2 hours ago

Sun, Sep 7 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$225 Roundtrip, found 2 hours ago

$225

Roundtrip

found 2 hours 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 2 hours ago

Thu, Sep 11 - Mon, Sep 15

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 2 hours ago

$237

Roundtrip

found 2 hours 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 2 hours ago

Fri, Sep 12 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 2 hours ago

$243

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Fri, Sep 12 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $243 found 2 hours ago

Mon, Sep 8 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$243 Roundtrip, found 2 hours ago

$243

Roundtrip

found 2 hours 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 2 hours ago

Fri, Jun 27 - Sat, Jul 5

MDW

Midway Intl.

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Portland Intl. Jetport

$250 Roundtrip, found 5 days ago

$250

Roundtrip

found 5 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 5 days ago

Sat, Sep 6 - Tue, Sep 16

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 2 hours ago

$253

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Sat, Sep 6 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $253 found 2 hours ago

Sun, Sep 7 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$258 Roundtrip, found 2 hours ago

$258

Roundtrip

found 2 hours 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 2 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 4 days ago

$259

Roundtrip

found 4 days 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 4 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 4 days ago

$259

Roundtrip

found 4 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $259 found 4 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$260 Roundtrip, found 4 days ago

$260

Roundtrip

found 4 days 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 4 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$263 Roundtrip, found 4 days ago

$263

Roundtrip

found 4 days ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $263 found 4 days ago

Wed, Jul 30 - Sat, Aug 9

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$270 Roundtrip, found 3 days ago

$270

Roundtrip

found 3 days 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 3 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$271 Roundtrip, found 4 days ago

$271

Roundtrip

found 4 days 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 4 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$277 Roundtrip, found 4 days ago

$277

Roundtrip

found 4 days 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 4 days ago

Tue, Sep 9 - Wed, Sep 17

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 2 hours ago

$279

Roundtrip

found 2 hours ago

Select Delta flight, departing Tue, Sep 9 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 17, priced at $279 found 2 hours ago

Thu, Sep 11 - Sat, Sep 13

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$280 Roundtrip, found 2 hours ago

$280

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Thu, Sep 11 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $280 found 2 hours ago