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

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save on select hotels after you book a flight*
    trophy illustration

    Find the right fit

    We search billions of combinations of flights to help you find your next adventure

Frequently asked questions

How long does it take to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)?
United Airlines operates a direct flight heading off from O'Hare Intl. Airport (ORD) at 11:20AM and landing at Portland Intl. Jetport at 2:51PM — a flight duration of 2 hours and 31 minutes. Lock in a seat, bring something to keep you busy and the time will race by.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) last minute?
When it comes to booking your flights, being organized pays off. While it may be possible to pick up a last-minute deal on an ORD to Portland Intl. Jetport Airport (PWM) flight, prices usually don't get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days in advance. For international journeys it's between three and four months.
What airline has the least delays from ORD to PWM?
Depart with United Airlines from O'Hare Intl. Airport (ORD) to PWM and you're more likely to land at the time that's on your ticket. This airline is the best performer on this route, with 100% of services arriving on time. If your flight happens to get delayed, the free Expedia App is a good way to stay up to date. It'll give you real-time trip notifications, from flight delays to gate changes.
What airports do you fly into for Portland from Chicago?
Portland Intl. Jetport Airport (PWM), Augusta State Airport (AUG) and Brunswick, ME (NHZ-Brunswick Executive) are your options when flying from Chicago to Portland. Roughly 5 kilometers west of the heart of Portland, Portland Intl. Jetport Airport (PWM) is the city's main hub. Keep in mind factors such as flight schedules and the distance to your hotel before you select an airport. Portland Museum of Art and University of Southern Maine are a couple of leading attractions to add to your must-see list when you arrive at your destination.
What are the most popular departure times for flights from ORD to PWM?
Between 11:00 AM - 12:00 PM is when you'll find the largest number of United Airlines flights going from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM). Our recommendation? Get up and away earlier in the day. With air traffic yet to build up around airports, your odds of boarding a delay-free flight are higher.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport?
Plans can get upended, so Expedia is here to help make things easier. First, access your ORD to Portland Intl. Jetport itinerary through the Expedia Trips portal and check the ticket rules and conditions about what sorts of changes are allowed. If you purchased your fare in the last 24 hours, some carriers will let you cancel for free and organize new flights. If you bought your fare more than 24 hours ago, contact us via our Customer Service portal to see how we can assist.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Portland Intl. Jetport
Distance
1435 km
Average flight time
3 hours 28 mins

Book with confidence

Chicago to Portland Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Portland offer the perfect respite. Not only does exploring Portland provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Portland may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Portland are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Portland more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Portland is now!

Chicago to Portland Flights

Explore a world of travel with Expedia