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Cheap PWM to ORD Flights

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

Portland to Chicago route information

Origin Airport Portland Intl. Jetport
Destination Airport O'Hare Intl.
Airlines Serving American Airlines, Delta, Frontier Airlines, JetBlue Airways, United
Flight Price $182
Distance 897 mi



Cheap PWM to ORD Flights

  • Question : How much is a plane ticket to Chicago (ORD) from Portland (PWM)?
    Answer : Cost can range from $218 to $997, prices for PWM to ORD change less than most routes in the United States. However, usually the sooner you book, the better price you get.
  • Question : How many flights are there per day from Portland to Chicago?
    Answer : Each day is different, but on average, you can expect to see four available departure times. Compared to the average route departing the United States with nine flight times, you won't have as many options as most.
  • Question : What is the cheapest airline flying from Portland to Chicago?
    Answer : JetBlue Airways is the leader in keeping costs down for their passengers over the next three months. Fares are being booked at just $218, which is a bargain when compared to the high-end bookings of $997.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Portland to Chicago is on Sunday. So, if you want to save a little money on your next holiday look for flights on that day.
  • Question : What day has the most flight time options?
    Answer : The day with the most departure times for this route is Saturday with five options. Thursday currently offers the fewest number of flight times with only three options.
  • Question : How much time do people spend in Chicago?
    Answer : The average time spent in Chicago by passengers from Portland is five days.
  • Question : Which airline has the least delays from Portland to Chicago?
    Answer : Booking with NetJets Aviation means you will arrive to Chicago about the time you were supposed to. In fact, this timely airline has a 100% average for landing before the plane turns into a pumpkin. Of course, it never hurts to be prepared. If you’re on Shuttle America, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Maine 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 Maine 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, we’ll pair you up with PWM to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Maine 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.

Jun 27, 2019

Staff at Portland airport wonderful for stressed traveler, give them a raise!

Jun 19, 2019

On time!!

Jun 16, 2019

Good flight

Jun 2, 2019

Traveling to Portland. The steward was helpful he helping me get off the plane with crutches. He walked behind me all the way down the ramp. He was very sweet and endearing. I greatly appreciated the care.

May 27, 2019

Good crew.

May 4, 2019

The pilot from Portland Me to Chicago was outstanding He kept us up to date on everything, not something I get often on my flights I’ve taken

Apr 19, 2019

Diane was a wonderful flight attendant! Great conversation.

Mar 13, 2019

Didn’t care that the flight was delayed from taking off and no wi fi had to pay

Feb 20, 2019

my flight was delayed so i would miss my connection and meeting on west coast. Gate agent was AMAZING!! at PWM. she got me on another flight to CA so I made my meeting. Incredible job by incredible employee - couldn't see her name tag. brown hair middle aged female. 12/19 6 AM at PWM

Nov 18, 2018

Seats are too tight. Food was just pretzels. Plane too hot on way from Chicago to Portland. Need to let folks know about why delays are happening.