The cheapest times to fly from PWM to ORD are

  • August 6th to February 25th (except the weeks of November 26th, January 1st, and February 12th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from PWM to ORD is early September. Prices can be as high as $847 for Sunday flights during late July, or as low as $192 for Tuesday flights around early September.


When to Fly to Chicago

Flying from Portland, ME (PWM) to Chicago, IL (ORD) will usually cost between $285 to $490 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early September with an average ticket price of $279. Due to high demand the most expensive time to fly is late July, with an average price of $510. Planning your trip to low-cost times can easily save you $231 on economy flights and even more on first-class flights. Generally, any price below $373 can be considered a good price for a round-trip PWM to ORD flight.

See below for a graph of average weekly prices for the PWM to ORD route. All prices are for round-trip tickets in USD.

PWM to ORD Flight Prices

Compared to other flights, the PWM to ORD flight is much cheaper than the average and costs much less than the average flight leaving from Portland. The average price per mile (for a direct flight) is $0.26, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $84 (20%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $342. Return trip prices are from the ORD to PWM flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from PWM to ORD can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 2 hour 36 minutes may be realistic.


Alternative Nearby Airports

Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is a nonstop flight from PWM to ORD while comparing.

Destination alternative #1: General Mitchell International Airport (MKE) in Milwaukee, WI

  • 67 miles (108 km) away from ORD
  • Usually 12.21% less expensive than ORD
  • 1-layover flights available

See PWM to MKE flights

Destination alternative #2: Dane County Regional-Truax Field Airport (MSN) in Madison, WI

  • 108 miles (174 km) away from ORD
  • Usually 9.40% less expensive than ORD
  • 1-layover flights available

See PWM to MSN flights

Destination alternative #3: Gerald R. Ford International Airport (GRR) in Grand Rapids, MI

  • 137 miles (220 km) away from ORD
  • Usually 9.26% less expensive than ORD
  • 1-layover flights available

See PWM to GRR flights


Flight Hacking PWM to ORD

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from PWM to ORD — but Champion Traveler does!

Hack #1: New York, NY (PWM > LGA > ORD)

  • Price for both tickets: $365
  • Average savings: $8 (2.01%)

See PWM to LGA flights


Flight Questions Answered

Still have questions about flying from PWM to ORD? We’ve got answers.

Which airlines fly this route?

You can find 8 major airlines flying this route most often: American, Cape Air, Delta, Emirates, Frontier, Hawaiian, JetBlue, United, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Portland International Jetport Airport?

The distance between the two airports is roughly 898 miles or 1445 kilometers.

How long does it take to fly from PWM to ORD?

The real-world flight time for a nonstop PWM to ORD flight is about 2 hour 36 minutes.

How many flights go between Portland, ME and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 65 available flights from PWM to ORD.


Airport Location Info


Departing Airport

Origination code PWM
Origination airport name Portland International Jetport Airport
City Portland, ME
Country the United States
Latitude 43.6
Longitude -70.3

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


Late and Early Flight Data

Flights from PWM to ORD tend to depart as late as the average flight. According to our recently updated data, 24% of flights departed 5 or more minutes late, and 24% of flights left 5 or more minutes early. On average you can expect to leave ORD heading for PWM about 18 minutes late. This does significantly impact arrival time, as the average landing time in Chicago, IL is about 13 minutes late. The numbers below show a recent average of take-off times versus the scheduled departure flight:

  • SkyWest: 2 minutes late
  • United: 26 minutes late
  • Envoy: 11 minutes late
  • Some airlines not reporting


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.