Flights from Portland to Chicago

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.

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $167 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$177 Roundtrip, found 2 days ago

$177

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $177 found 2 days ago

Thu, May 29 - Fri, May 30

PDX

Portland Intl.

ORD

O'Hare Intl.

$179 Roundtrip, found 2 days ago

$179

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Fri, May 30, priced at $179 found 2 days ago

Thu, May 29 - Fri, Jun 6

PDX

Portland Intl.

ORD

O'Hare Intl.

$186 Roundtrip, found 2 days ago

$186

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Fri, Jun 6, priced at $186 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$194 Roundtrip, found 2 days ago

$194

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $194 found 2 days ago

Thu, May 29 - Thu, Jun 5

PDX

Portland Intl.

ORD

O'Hare Intl.

$196 Roundtrip, found 2 days ago

$196

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Thu, Jun 5, priced at $196 found 2 days ago

Thu, May 29 - Thu, May 29

PDX

Portland Intl.

ORD

O'Hare Intl.

$199 Roundtrip, found 2 days ago

$199

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Thu, May 29, priced at $199 found 2 days ago

Thu, May 29 - Sat, Jun 7

PDX

Portland Intl.

ORD

O'Hare Intl.

$203 Roundtrip, found 2 days ago

$203

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $203 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$208 Roundtrip, found 2 days ago

$208

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $208 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$212 Roundtrip, found 2 days ago

$212

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $212 found 2 days ago

Thu, May 29 - Sun, Jun 8

PDX

Portland Intl.

ORD

O'Hare Intl.

$214 Roundtrip, found 2 days ago

$214

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, May 29 from Portland Intl. to O'Hare Intl., returning Sun, Jun 8, priced at $214 found 2 days ago

Thu, May 8 - Sun, May 11

PDX

Portland Intl.

ORD

O'Hare Intl.

$218 Roundtrip, found 5 days ago

$218

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, May 8 from Portland Intl. to O'Hare Intl., returning Sun, May 11, priced at $218 found 5 days ago

Mon, Jun 2 - Sat, Jun 7

PDX

Portland Intl.

ORD

O'Hare Intl.

$218 Roundtrip, found 2 days ago

$218

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Jun 2 from Portland Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $218 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$221 Roundtrip, found 2 days ago

$221

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $221 found 2 days ago

Tue, Jun 3 - Sat, Jun 7

PDX

Portland Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 2 days ago

$227

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Tue, Jun 3 from Portland Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $227 found 2 days ago

Mon, Jun 2 - Sun, Jun 8

PDX

Portland Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Jun 2 from Portland Intl. to O'Hare Intl., returning Sun, Jun 8, priced at $228 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 2 days ago

$230

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $230 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 2 days ago

$238

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $238 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 2 days ago

$238

Roundtrip

found 2 days ago

Select United flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $238 found 2 days ago

Sun, Jun 1 - Tue, Jun 3

PDX

Portland Intl.

ORD

O'Hare Intl.

$238 Roundtrip, found 2 days ago

$238

Roundtrip

found 2 days ago

Select American Airlines flight, departing Sun, Jun 1 from Portland Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $238 found 2 days ago