Cheap Flights To Wolfeboro 2026

Wolfeboro Flights as Low as $142

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.

Sat, Sep 19 - Sat, Sep 26

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$142 Roundtrip, found 1 day ago

$142

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Sep 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 26, priced at $142 found 1 day ago

Sat, Sep 19 - Sat, Sep 26

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$147 Roundtrip, found 1 day ago

$147

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Sep 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 26, priced at $147 found 1 day ago

Sat, Sep 19 - Sat, Sep 26

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$152 Roundtrip, found 1 day ago

$152

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Sep 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 26, priced at $152 found 1 day ago

Tue, Aug 11 - Fri, Aug 21

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Aug 11 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $177 found 1 day ago

Tue, Aug 11 - Tue, Aug 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$185 Roundtrip, found 1 day ago

$185

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Aug 11 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 18, priced at $185 found 1 day ago

Sat, Sep 19 - Sat, Sep 26

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$199 Roundtrip, found 1 day ago

$199

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Sep 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 26, priced at $199 found 1 day ago

Tue, Sep 8 - Wed, Sep 9

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 Tue, Sep 8 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Sep 9, priced at $201 found 4 days ago

Fri, Sep 18 - Wed, Sep 23

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$205 Roundtrip, found 2 days ago

$205

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Fri, Sep 18 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Sep 23, priced at $205 found 2 days ago

Fri, Sep 18 - Wed, Sep 23

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 2 days ago

$210

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 18 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Sep 23, priced at $210 found 2 days ago

Fri, Sep 18 - Wed, Sep 23

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$215 Roundtrip, found 2 days ago

$215

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Fri, Sep 18 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Sep 23, priced at $215 found 2 days ago

Tue, Aug 11 - Tue, Aug 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$220 Roundtrip, found 1 day ago

$220

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Aug 11 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 18, priced at $220 found 1 day ago

Wed, Sep 23 - Fri, Oct 2

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$257 Roundtrip, found 2 days ago

$257

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 23 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Oct 2, priced at $257 found 2 days ago

Tue, Aug 11 - Tue, Aug 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$271 Roundtrip, found 1 day ago

$271

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Aug 11 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 18, priced at $271 found 1 day ago

Tue, Aug 11 - Tue, Aug 18

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$281 Roundtrip, found 1 day ago

$281

Roundtrip

found 1 day ago

Select United flight, departing Tue, Aug 11 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Aug 18, priced at $281 found 1 day ago

Sat, Sep 19 - Sat, Sep 26

CMH

John Glenn Columbus Intl.

PWM

Portland Intl. Jetport

$318 Roundtrip, found 1 day ago

$318

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Sat, Sep 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 26, priced at $318 found 1 day ago

Tue, Aug 18 - Tue, Aug 25

TXK

Texarkana Regional

PWM

Portland Intl. Jetport

$424 Roundtrip, found 1 day ago

$424

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Aug 18 from Texarkana Regional to Portland Intl. Jetport, returning Tue, Aug 25, priced at $424 found 1 day ago