Flights from Sanford to Chicago

Cheapest flights from Sanford

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.

Wed, Jul 16 - Wed, Jul 23

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$210 Roundtrip, found 2 days ago

$210

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 23, priced at $210 found 2 days ago

Wed, Jul 16 - Sat, Jul 19

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$215 Roundtrip, found 2 days ago

$215

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Portland Intl. Jetport to O'Hare Intl., returning Sat, Jul 19, priced at $215 found 2 days ago

Tue, Jul 15 - Wed, Jul 23

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jul 15 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 23, priced at $228 found 2 days ago

Fri, Jul 18 - Wed, Jul 23

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$233 Roundtrip, found 2 days ago

$233

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 23, priced at $233 found 2 days ago

Tue, Jul 15 - Wed, Jul 16

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$233 Roundtrip, found 2 days ago

$233

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jul 15 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 16, priced at $233 found 2 days ago

Fri, Jul 18 - Sat, Jul 19

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$238 Roundtrip, found 2 days ago

$238

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sat, Jul 19, priced at $238 found 2 days ago

Sat, Jul 19 - Wed, Jul 23

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$262 Roundtrip, found 2 days ago

$262

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 23, priced at $262 found 2 days ago

Sat, Jul 19 - Tue, Jul 22

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$265 Roundtrip, found 2 days ago

$265

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Jul 19 from Portland Intl. Jetport to O'Hare Intl., returning Tue, Jul 22, priced at $265 found 2 days ago

Sat, Jul 19 - Sat, Jul 26

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$267 Roundtrip, found 2 days ago

$267

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Jul 19 from Portland Intl. Jetport to O'Hare Intl., returning Sat, Jul 26, priced at $267 found 2 days ago

Thu, Jul 17 - Tue, Jul 22

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$290 Roundtrip, found 2 days ago

$290

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Jul 17 from Portland Intl. Jetport to O'Hare Intl., returning Tue, Jul 22, priced at $290 found 2 days ago

Wed, Jul 16 - Fri, Jul 25

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$296 Roundtrip, found 2 days ago

$296

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Portland Intl. Jetport to O'Hare Intl., returning Fri, Jul 25, priced at $296 found 2 days ago

Tue, Jul 15 - Thu, Jul 17

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$298 Roundtrip, found 2 days ago

$298

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 15 from Portland Intl. Jetport to O'Hare Intl., returning Thu, Jul 17, priced at $298 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$298 Roundtrip, found 2 days ago

$298

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $298 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$308 Roundtrip, found 2 days ago

$308

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $308 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$315 Roundtrip, found 2 days ago

$315

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $315 found 2 days ago

Wed, Jul 16 - Fri, Jul 18

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$316 Roundtrip, found 2 days ago

$316

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Wed, Jul 16 from Portland Intl. Jetport to O'Hare Intl., returning Fri, Jul 18, priced at $316 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$318 Roundtrip, found 2 days ago

$318

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $318 found 2 days ago

Thu, Jul 17 - Wed, Jul 23

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$320 Roundtrip, found 2 days ago

$320

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Jul 17 from Portland Intl. Jetport to O'Hare Intl., returning Wed, Jul 23, priced at $320 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$322 Roundtrip, found 2 days ago

$322

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $322 found 2 days ago

Fri, Jul 18 - Sun, Jul 20

PWM

Portland Intl. Jetport

ORD

O'Hare Intl.

$325 Roundtrip, found 2 days ago

$325

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Jul 18 from Portland Intl. Jetport to O'Hare Intl., returning Sun, Jul 20, priced at $325 found 2 days ago