Skip to main content
Beginning of main content

PWM (Portland) to ORD (Chicago) Flights $295.8

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap PWM to ORD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$357.60

Interesting Facts About Flights from Portland to Chicago (PWM to ORD)

Question : If your plans are flexible, have you considered changing your departure day?
Answer : Tuesday is your lowest-cost day to fly in August. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : What's the likelihood of you being delayed on this route?
Answer : PWM to ORD currently scores 3 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 3 stars, you should feel slightly worried about getting to Chicago on time.

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : NetJets Aviation will have you to ORD on time 100% of the time. Don't spend more time waiting in an airport than you have to and stick with NetJets Aviation on this route. Hopefully they keep that perfect record alive.

Question : How often are flights late from Portland International Jetport (PWM) to O'Hare International Airport (ORD)?
Answer : Flights from PWM to ORD are on time 76% of the time, ranking in the 50th percentile worldwide. When a flight is late, it's a 39-minute delay on average.

Question : Are you paying the cheapest or highest price for your ticket to Chicago?
Answer : Prices for this trip tend to change more than other flights in the United States. They can vary from $200 to $1,178. However, the sooner you book, the more you'll be able to save.

Question : How long will the flight typically be from Portland International Jetport (PWM) to O'Hare International Airport (ORD)?
Answer : Flying from PWM to ORD typically takes about three hours and four minutes.

Question : Who struggles with getting their passengers to O'Hare International Airport (ORD) on time?
Answer : If you're flying SkyWest Airlines to Chicago from Portland, you may be tardy as they're late 38% of the time. If you’re on SkyWest Airlines, be sure to sign up for the delay notifications to stay up to date with your flight’s status.