Flights from Chicago to Waterboro

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, Jul 22 - Wed, Jul 23

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$203 Roundtrip, found 3 hours ago

$203

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $203 found 3 hours ago

Tue, Jul 22 - Fri, Jul 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$210 Roundtrip, found 3 hours ago

$210

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Tue, Jul 22 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 25, priced at $210 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$232 Roundtrip, found 3 hours ago

$232

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $232 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$237 Roundtrip, found 3 hours ago

$237

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $237 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$246 Roundtrip, found 3 hours ago

$246

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $246 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$253 Roundtrip, found 3 hours ago

$253

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $253 found 3 hours ago

Fri, Jun 27 - Sat, Jul 5

MDW

Midway Intl.

PWM

Portland Intl. Jetport

$254 Roundtrip, found 6 days ago

$254

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Jun 27 from Midway Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $254 found 6 days ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 3 hours ago

$259

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $259 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$259 Roundtrip, found 3 hours ago

$259

Roundtrip

found 3 hours 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 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$261 Roundtrip, found 3 hours ago

$261

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $261 found 3 hours ago

Fri, Jul 18 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$269 Roundtrip, found 3 hours ago

$269

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Fri, Jul 18 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $269 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$270 Roundtrip, found 3 hours ago

$270

Roundtrip

found 3 hours ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $270 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$272 Roundtrip, found 3 hours ago

$272

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $272 found 3 hours ago

Mon, Jul 21 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$273 Roundtrip, found 3 hours ago

$273

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $273 found 3 hours ago

Thu, Jul 17 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$278 Roundtrip, found 3 hours ago

$278

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Thu, Jul 17 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $278 found 3 hours ago

Mon, Jul 21 - Fri, Jul 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$279 Roundtrip, found 3 hours ago

$279

Roundtrip

found 3 hours ago

Select Delta flight, departing Mon, Jul 21 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 25, priced at $279 found 3 hours ago

Sat, Jul 19 - Fri, Jul 25

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$280 Roundtrip, found 3 hours ago

$280

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Jul 25, priced at $280 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$281 Roundtrip, found 3 hours ago

$281

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $281 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$282 Roundtrip, found 3 hours ago

$282

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $282 found 3 hours ago

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

PWM

Portland Intl. Jetport

$283 Roundtrip, found 3 hours ago

$283

Roundtrip

found 3 hours ago

Select United flight, departing Sat, Jul 19 from O'Hare Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $283 found 3 hours ago