€111 Cheap Flights Portland to Chicago (PWM-ORD)

View €111 flight on Wed, 3 Sep 2025Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare Intl. Airport (ORD)

  • 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 15% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Portland to Chicago (PWM-ORD)

Prices were available within the past 7 days and start at €111 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Portland (PWM) to Chicago (ORD)

August is typically the cheapest month to fly

From €124 - €331 per traveller.

Graph displaying average flight prices per month

Portland to Chicago route information
Origin airport
Portland Intl. Jetport
Destination airport
O'Hare Intl.
Distance
1435 km
Average flight time
1 hour 56 mins

Perfect flights from Portland to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Portland to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Chicago, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Portland Intl. Jetport to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from €111 and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at O'Hare Intl. and explore Chicago and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your PWM to ORD travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Portland Intl. Jetport Airport (PWM) to ORD?
If you're planning on travelling 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 kilometres 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 travellers 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.

Explore a world of travel with Expedia

*Available to Expedia members.