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
04 Sep
PDX
12:20 pm
Portland airport
8h 43m
1 Stop
11:03 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
10 Sep
ORD
2:40 am
Chicago O'Hare Intl airport
7h 16m
1 Stop
7:56 am
PDX
Portland airport
232 USD
Spirit Airlines
Spirit Airlines
10 Sep
PDX
6:46 am
Portland airport
7h 53m
1 Stop
4:39 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
18 Sep
ORD
2:40 am
Chicago O'Hare Intl airport
7h 16m
1 Stop
7:56 am
PDX
Portland airport
232 USD
Spirit Airlines
Spirit Airlines
11 Sep
PDX
6:46 am
Portland airport
7h 53m
1 Stop
4:39 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
16 Sep
ORD
10:26 am
Chicago O'Hare Intl airport
11h 05m
1 Stop
7:31 pm
PDX
Portland airport
232 USD
American Airlines
American Airlines
07 Nov
PDX
6:00 am
Portland airport
4h 03m
12:03 pm
ORD
Chicago O'Hare Intl airport
American Airlines
10 Nov
ORD
1:45 am
Chicago O'Hare Intl airport
4h 20m
4:05 am
PDX
Portland airport
296 USD
United Airlines
United Airlines
04 Nov
PDX
6:00 am
Portland airport
3h 44m
11:44 am
ORD
Chicago O'Hare Intl airport
United Airlines
12 Nov
ORD
11:04 am
Chicago O'Hare Intl airport
8h 55m
1 Stop
5:59 pm
PDX
Portland airport
275 USD
United Airlines
United Airlines
01 Nov
PDX
12:11 am
Portland airport
3h 49m
6:00 am
ORD
Chicago O'Hare Intl airport
United Airlines
12 Nov
ORD
11:04 am
Chicago O'Hare Intl airport
8h 55m
1 Stop
5:59 pm
PDX
Portland airport
275 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
CHEAPEST MONTH TO FLY
August
The cheapest time of year to fly to Chicago from Portland is August. Most expensive is March
CHEAPEST DAY TO FLY
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
CHEAPEST TIME TO FLY
in the Afternoon
Portland to Chicago flights are approximately 25% more expensive in the Morning than in the Afternoon
CHEAPEST AIRLINE
Sun Country Air
Sun Country Air, Frontier, and Spirit Airlines are the most popular carriers operating from Portland to Chicago
CHEAPEST ROUTE
Portland - Chicago O'Hare Intl
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
CHEAPEST TIME TO BOOK
40 days before
The cheapest time to buy a flight from Portland to Chicago is approximately 40 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 49m
The fastest flight from Portland to Chicago takes 3h 49m.
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

Flights from Portland to:

Flights to Chicago from:

  • Portland
  • Oregon
  • United States
  • North America