The cheapest times to fly from PWM to MDW are

  • January 1st to March 4th
  • April 23rd to May 6th
  • August 13th to March 4th (except the weeks of October 8th, November 19th, November 26th, December 17th, and December 24th)

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 MDW is early December. Prices can be as high as $920 for Friday flights during early to mid April, or as low as $315 for Tuesday flights around early December.


When to Fly to Chicago

Flying from Portland, ME (PWM) to Chicago, IL (MDW) will usually cost between $344 to $645 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early December with an average ticket price of $343. Due to high demand the most expensive time to fly is early to mid April, with an average price of $670. Planning your trip to low-cost times can easily save you $328 on economy flights and even more on first-class flights. Generally, any price below $421 can be considered a good price for a round-trip PWM to MDW flight.

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

PWM to MDW Flight Prices

Compared to other flights, the PWM to MDW flight is much cheaper than the average and costs less than the average flight leaving from Portland. The average price per mile (for a direct flight) is $0.29, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Fridays 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 $113 (23%) 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 $388. Return trip prices are from the MDW 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 MDW can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 2 hour 35 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 MDW while comparing.

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

  • 81 miles (130 km) away from MDW
  • Usually 22.33% less expensive than MDW
  • 1-layover flights available

See PWM to MKE flights

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

  • 124 miles (200 km) away from MDW
  • Usually 19.83% less expensive than MDW
  • 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 MDW
  • Usually 19.71% less expensive than MDW
  • 1-layover flights available

See PWM to GRR flights

Destination alternative #4: Chicago O’Hare International Airport (ORD) in Chicago, IL

  • 15 miles (24 km) away from MDW
  • Usually 11.52% less expensive than MDW
  • Nonstop flights available

See PWM to ORD flights

Destination alternative #5: Fort Wayne International Airport (FWA) in Fort Wayne, IN

  • 144 miles (232 km) away from MDW
  • Usually 18.88% less expensive than MDW
  • 1-layover flights available

See PWM to FWA flights

Destination alternative #6: South Bend International Airport (SBN) in South Bend, IN

  • 74 miles (119 km) away from MDW
  • Usually 11.16% less expensive than MDW
  • 1-layover flights available

See PWM to SBN flights


Flight Questions Answered

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

Which airlines fly this route?

You can find 4 major airlines flying this route most often: Cape Air, Delta, Southwest, United, and potentially more during busy seasons.

How far away is it from Chicago Midway International Airport to Portland International Jetport Airport?

The distance between the two airports is roughly 893 miles or 1437 kilometers.

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

The real-world flight time for a nonstop PWM to MDW flight is about 2 hour 35 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 64 available flights from PWM to MDW.


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 MDW
Destination airport name Chicago Midway International Airport
City Chicago, IL
Country the United States
Latitude 41.8
Longitude -87.8


Late and Early Flight Data

Flights from PWM to MDW tend to depart late almost never compared to the average flight. According to our recently updated data, 0% of flights departed 5 or more minutes late, and 25% of flights left 5 or more minutes early. On average you can expect to leave MDW heading for PWM about 4 minutes early. This does significantly impact arrival time, as the average landing time in Chicago, IL is about 7 minutes early. The numbers below show a recent average of take-off times versus the scheduled departure flight:

  • Southwest: 4 minutes early
  • 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.