Chicago to Portland Flights (CHI-PDX) from $35

Wander Wisely with exceptional service, 24/7 support

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Selected fares from Chicago to Portland

The cheapest prices found with in the last 7 days for return flights were $69 and $35 for one-way flights to Portland for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, May 11 - Wed, May 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$69 Roundtrip, just found
$69
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 11 from O'Hare Intl. to Portland Intl., returning Wed, May 15, priced at $69 just found
Frontier Airlines
Sat, May 4 - Sat, May 11
MDW
Midway Intl.
PDX
Portland Intl.
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 4 from Midway Intl. to Portland Intl., returning Sat, May 11, priced at $128 found 5 days ago
Alaska Airlines
Wed, Aug 7 - Wed, Aug 14
ORD
O'Hare Intl.
PDX
Portland Intl.
$179 Roundtrip, found 14 hours ago
$179
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Wed, Aug 7 from O'Hare Intl. to Portland Intl., returning Wed, Aug 14, priced at $179 found 14 hours ago

Save more with Portland Flight + Hotel packages

Prices and availability subject to change. Additional terms may apply.
Park Lane Suites and Inn

Park Lane Suites and Inn

2.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
Washington Plaza Apartments

Washington Plaza Apartments

3 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
Hilton Portland Downtown

Hilton Portland Downtown

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
The Hotel Zags Portland

The Hotel Zags Portland

4 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
Hotel deLuxe

Hotel deLuxe

4 out of 5
per person
Jun 14 - Jun 18
Roundtrip flight included
Chicago (ORD) to Portland (PDX)
Don't see what you're looking for?
See all available trips from Chicago to Portland
View all trips