Cheap Flights from Portland (PWM) to Chicago (ORD)

Bundle Your Flight + Hotel & Save!

    Plan, book, fly with confidence
    trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
    bex rewards loyalty icon
    Book smarter
    Save up to 45% on select hotels after you book a flight*
    payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in
Flights from Portland (PWM) to Chicago (ORD)
Origin airport
Portland Intl. Jetport
Destination airport
O'Hare Intl.
Distance
1435 km
Average flight time
2 hours 1 min

Portland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Portland to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with PWM to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Portland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Portland Intl. Jetport Airport (PWM) to ORD?
If you’re planning on traveling between Portland Intl. Jetport and ORD, round-trip flights start from . This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don’t hang about. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Portland Intl. Jetport Airport (PWM) to ORD?
Every airline has its own terms and conditions. If you decide to cancel your trip, head to our Customer Service Portal.
How do I find cheap flights from PWM to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Portland Intl. Jetport to O’Hare Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from PWM to O'Hare Intl. Airport (ORD)?
A flight distance of just 1,450 kilometers separates Portland and Chicago. Once you’re in the air, you won’t have time to do much more than read the magazine in your seat pocket.
Which airlines fly direct from Portland Intl. Jetport to O'Hare Airport?
United Airlines (UA) is one of the preferred choices for many travelers flying between PWM and ORD. Take your pick of the 60 flights it offers on this route each month. Another airline operating on this route is American Airlines (AA). You’ll have 8 flights each month to take your pick of.
Are PWM to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Portland Intl. Jetport to ORD at the last minute could be your ticket to a cheap deal. However, it could end up costing a great deal more! If you’d prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back often as deals are updated on Expedia all the time.
*Available to Expedia members.