Cheap flights from Portland to Chicago

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Easily compare round-trip flights from Portland to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Portland to Chicago by changing tabs
Quickest
Cheapest
Spirit Airlines
Spirit Airlines
22 Oct
PDX
6:46 am
Portland airport
13h 51m
1 Stop
10:37 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
28 Oct
ORD
4:54 pm
Chicago O'Hare Intl airport
17h 05m
1 Stop
7:59 am
+1
PDX
Portland airport
139 USD
Spirit Airlines
Spirit Airlines
28 Oct
PDX
12:11 pm
Portland airport
19h 26m
2 Stops
9:37 am
+1
ORD
Chicago O'Hare Intl airport
Spirit Airlines
29 Oct
ORD
4:54 pm
Chicago O'Hare Intl airport
17h 05m
1 Stop
7:59 am
+1
PDX
Portland airport
172 USD
Spirit Airlines
Spirit Airlines
23 Oct
PDX
11:00 pm
Portland airport
15h 59m
1 Stop
4:59 pm
+1
ORD
Chicago O'Hare Intl airport
Spirit Airlines
30 Oct
ORD
7:51 am
Chicago O'Hare Intl airport
9h 04m
2 Stops
2:55 pm
PDX
Portland airport
174 USD
American Airlines
American Airlines
13 Feb
PDX
6:00 am
Portland airport
4h 03m
12:03 pm
ORD
Chicago O'Hare Intl airport
American Airlines
18 Feb
ORD
9:50 am
Chicago O'Hare Intl airport
4h 35m
12:25 pm
PDX
Portland airport
264 USD
Alaska Airlines
Alaska Airlines
04 Feb
PDX
2:30 am
Portland airport
4h 05m
8:35 am
ORD
Chicago O'Hare Intl airport
Alaska Airlines
25 Feb
ORD
9:50 am
Chicago O'Hare Intl airport
4h 35m
12:25 pm
PDX
Portland airport
237 USD
Alaska Airlines
Alaska Airlines
11 Feb
PDX
2:30 am
Portland airport
4h 05m
8:35 am
ORD
Chicago O'Hare Intl airport
Alaska Airlines
19 Feb
ORD
9:50 am
Chicago O'Hare Intl airport
4h 35m
12:25 pm
PDX
Portland airport
237 USD

How to get the cheapest flight ticket from Portland to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
January
The cheapest time of year to fly to Chicago from Portland is January. Most expensive is December
What is the cheapest day to fly to Chicago?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday
When is the cheapest time to fly to Chicago?
in the afternoon
Portland to Chicago flights are approximately 13% more expensive in the morning than in the afternoon
What is the cheapest airline that flies to Chicago?
Frontier
Frontier, Sun Country Air, and Spirit Airlines are the most popular carriers operating from Portland to Chicago
What is the cheapest route?
Portland - Chicago O'Hare Intl
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
36 days before
The cheapest time to buy a flight from Portland to Chicago is approximately 36 days to departure
60
Days before departure
0

Flight information for Portland to Chicago (CHI - PDX)

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
Fastest flight time 3h 50m The fastest flight from Portland to Chicago takes 3h 50m.
Direct flights Every day Direct flights go from Portland to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Portland to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Seattle to Chicago
Fastest flight time
3h 44m
Cheapest price
163 USD
Seattle to Indianapolis
Fastest flight time
4h 10m
Cheapest price
193 USD
Portland to Indianapolis
Fastest flight time
7h 31m
Cheapest price
246 USD
Eugene to Chicago
Fastest flight time
3h 35m
Cheapest price
263 USD
View more

Flights from Portland to: