Chicago Portland - Cheap flights

Special flight deals from Chicago to Portland

Chicago - Portland
4 days
Sat 10 Oct
ORD-PDX· 1 stop
Frontier Airlines
Tue 13 Oct
PDX-ORD· Direct
Alaska Airlines
from325 USD
Chicago - Portland
8 days
Sat 10 Oct
ORD-PDX· 1 stop
Frontier Airlines
Sat 17 Oct
PDX-ORD· Direct
Alaska Airlines
from325 USD
Chicago - Portland
5 days
Sat 07 Nov
ORD-PDX· Direct
Alaska Airlines
Wed 11 Nov
PDX-ORD· 1 stop
Alaska Airlines
from330 USD
Chicago - Portland
5 days
Sat 07 Nov
ORD-PDX· Direct
Alaska Airlines
Wed 11 Nov
PDX-ORD· 1 stop
Alaska Airlines
from330 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from396 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from396 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from449 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from474 USD
Chicago - Portland
5 days
Tue 20 Oct
MDW-PDX· 1 stop
Delta Air Lines
Sat 24 Oct
PDX-MDW· 1 stop
Delta Air Lines
from474 USD
Chicago - Portland
6 days
Wed 07 Oct
ORD-PDX· 1 stop
Delta Air Lines
Mon 12 Oct
PDX-ORD· 1 stop
Delta Air Lines
from302 USD
Chicago - Portland
6 days
Wed 07 Oct
ORD-PDX· 1 stop
Delta Air Lines
Mon 12 Oct
PDX-ORD· 1 stop
Delta Air Lines
from302 USD
Chicago - Portland
6 days
Sat 10 Oct
ORD-PDX· 1 stop
Frontier Airlines
Thu 15 Oct
PDX-ORD· 1 stop
Delta Air Lines
from328 USD
Chicago - Portland
6 days
Sat 10 Oct
ORD-PDX· 1 stop
Frontier Airlines
Thu 15 Oct
PDX-ORD· 1 stop
Delta Air Lines
from328 USD
Chicago - Portland
5 days
Mon 28 Sep
ORD-PDX· 1 stop
Frontier Airlines
Fri 02 Oct
PDX-ORD· 1 stop
Frontier Airlines
from333 USD
Chicago - Portland
6 days
Sat 10 Oct
ORD-PDX· 1 stop
Frontier Airlines
Thu 15 Oct
PDX-ORD· 1 stop
Alaska Airlines
from335 USD

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Find the best time to book cheap flights to Portland

Flexible on travel dates? Discover the cheapest month to fly to Portland

Cheapest round-trip flight
from 300 USD
Cheapest month to travel
October
The cheapest day to fly
Friday
Lowest prices
3 months before

Sep

402 USD

Oct

300 USD

Nov

357 USD

Dec

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

When is the best time to buy flight tickets?

Find out how far in advance it's worth booking round-trip flights.

6 months before
from
507 USD
3 months before
from
372 USD
30 days before
from
589 USD
7 days before
from
678 USD
1 day before
from
485 USD

Discover the cheapest day to fly

Discover on which day of the week flights are usually the most affordable.

527 USD

Mon

465 USD

Tue

597 USD

Wed

511 USD

Thu

378 USD

Fri

430 USD

Sat

463 USD

Sun

General information

Local time (UTC-8)
21:53, 10 Sep 2026
Flight time from Chicago
4 h 25 min
Local currency
USD