Flights from Portland to Chicago

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Portland to Chicago flight comparison made easy

Below you can see the best fares for your 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
25 Sep
PDX
6:43 am
Portland airport
8h 12m
1 Stop
4:55 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
28 Sep
ORD
10:31 am
Chicago O'Hare Intl airport
10h 44m
1 Stop
7:15 pm
PDX
Portland airport
219 USD
Frontier
Frontier
07 Nov
PDX
2:26 am
Portland airport
11h 48m
1 Stop
4:14 pm
ORD
Chicago O'Hare Intl airport
Frontier
11 Nov
ORD
2:32 pm
Chicago O'Hare Intl airport
15h 03m
1 Stop
3:35 am
+1
PDX
Portland airport
222 USD
Spirit Airlines
Spirit Airlines
29 Aug
PDX
4:26 am
Portland airport
10h 13m
1 Stop
4:39 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
11 Sep
ORD
2:30 am
Chicago O'Hare Intl airport
7h 27m
1 Stop
7:57 am
PDX
Portland airport
226 USD
Delta
Delta
20 Nov
PDX
6:58 am
Portland airport
6h 46m
1 Stop
3:44 pm
ORD
Chicago O'Hare Intl airport
Delta
24 Nov
ORD
1:40 am
Chicago O'Hare Intl airport
4h 25m
4:05 am
PDX
Portland airport
280 USD
Sun Country Air
Sun Country Air
27 Aug
PDX
12:25 am
Portland airport
7h 00m
1 Stop
9:25 am
ORD
Chicago O'Hare Intl airport
Sun Country Air
31 Aug
ORD
2:45 pm
Chicago O'Hare Intl airport
4h 31m
5:16 pm
PDX
Portland airport
272 USD
Alaska Airlines
Alaska Airlines
13 Oct
PDX
10:15 am
Portland airport
3h 55m
4:10 pm
ORD
Chicago O'Hare Intl airport
Alaska Airlines
15 Oct
ORD
12:05 pm
Chicago O'Hare Intl airport
8h 45m
1 Stop
6:50 pm
PDX
Portland airport
252 USD

How to get the cheapest flight 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 for your trip
WHAT IS THE CHEAPEST MONTH TO FLY TO CHICAGO?
August
The cheapest time of year to fly to Chicago from Portland is August. Most expensive is June
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 evening
Portland to Chicago flights are approximately 129% more expensive in the morning than in the evening
WHAT IS THE CHEAPEST AIRLINE THAT FLIES TO CHICAGO?
Frontier
Frontier, Spirit Airlines, and Sun Country Air 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?
35 days before
The cheapest time to buy a flight from Portland to Chicago is approximately 35 days to departure
60
Days before departure
0

Flight information for Portland to Chicago

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
Fastest flight time 3h 43m The fastest flight from Portland to Chicago takes 3h 43m.
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 49m
Cheapest price
149 USD
Seattle to Chicago
Fastest flight time
4h 00m
Cheapest price
190 USD
Eugene to Chicago
Fastest flight time
3h 35m
Cheapest price
248 USD
Eugene to Chicago
Fastest flight time
8h 53m
Cheapest price
341 USD
View more

Flights from Portland to:

Flights to Chicago from:

  • Portland
  • Oregon
  • United States
  • North America