Flights from Portland to Winnetka

Cheapest flights from Portland

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 8 - Tue, Jul 15

PDX

Portland Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $137 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$141 Roundtrip, found 1 day ago

$141

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $141 found 1 day ago

Thu, Jul 10 - Tue, Jul 15

PDX

Portland Intl.

ORD

O'Hare Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Thu, Jul 10 from Portland Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $143 found 1 day ago

Fri, Jul 11 - Tue, Jul 15

PDX

Portland Intl.

ORD

O'Hare Intl.

$150 Roundtrip, found 1 day ago

$150

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Fri, Jul 11 from Portland Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $150 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $160 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $163 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $168 found 1 day ago

Thu, Jul 10 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$169 Roundtrip, found 1 day ago

$169

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Thu, Jul 10 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $169 found 1 day ago

Tue, Jul 8 - Sun, Jul 13

PDX

Portland Intl.

ORD

O'Hare Intl.

$170 Roundtrip, found 1 day ago

$170

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $170 found 1 day ago

Sun, May 11 - Mon, Jun 9

PDX

Portland Intl.

ORD

O'Hare Intl.

$176 Roundtrip, found 3 days ago

$176

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Sun, May 11 from Portland Intl. to O'Hare Intl., returning Mon, Jun 9, priced at $176 found 3 days ago

Thu, Jul 10 - Sun, Jul 13

PDX

Portland Intl.

ORD

O'Hare Intl.

$176 Roundtrip, found 1 day ago

$176

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Thu, Jul 10 from Portland Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $176 found 1 day ago

Wed, Jul 9 - Wed, Jul 16

PDX

Portland Intl.

ORD

O'Hare Intl.

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 9 from Portland Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $177 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$178 Roundtrip, found 1 day ago

$178

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $178 found 1 day ago

Fri, Jul 11 - Sun, Jul 13

PDX

Portland Intl.

ORD

O'Hare Intl.

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Fri, Jul 11 from Portland Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $183 found 1 day ago

Sun, May 11 - Mon, Jun 9

PDX

Portland Intl.

ORD

O'Hare Intl.

$185 Roundtrip, found 3 days ago

$185

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Sun, May 11 from Portland Intl. to O'Hare Intl., returning Mon, Jun 9, priced at $185 found 3 days ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$186 Roundtrip, found 1 day ago

$186

Roundtrip

found 1 day ago

Select United flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $186 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

PDX

Portland Intl.

ORD

O'Hare Intl.

$188 Roundtrip, found 1 day ago

$188

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Tue, Jul 8 from Portland Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $188 found 1 day ago

Sun, May 11 - Mon, Jun 9

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 3 days ago

$214

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sun, May 11 from Portland Intl. to O'Hare Intl., returning Mon, Jun 9, priced at $214 found 3 days ago

Fri, Aug 8 - Wed, Aug 13

PDX

Portland Intl.

ORD

O'Hare Intl.

$321 Roundtrip, found 3 days ago

$321

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Aug 8 from Portland Intl. to O'Hare Intl., returning Wed, Aug 13, priced at $321 found 3 days ago

Fri, Aug 8 - Wed, Aug 13

PDX

Portland Intl.

ORD

O'Hare Intl.

$351 Roundtrip, found 3 days ago

$351

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Aug 8 from Portland Intl. to O'Hare Intl., returning Wed, Aug 13, priced at $351 found 3 days ago