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Flights from Chicago to Portland – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

MDW to PWM flights and routes map MDW to PWM – All flight route options from Chicago Midway International, Illinois, USA to Portland International Jetport, Maine, USA. These flights are operated by 2 airlines. Fly non-stop with Southwest Airlines or choose from 4 different transit flights. The shortest flight time is 2 hours and 15 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA MDW Chicago Midway Chicago, IL, USA
USA PWM Portland Jetport, ME, USA
MDW
Chicago Midway
USAChicago, IL, USA
Portland Jetport
USAPortland, ME, USA
PWM
1 direct route found »
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4 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 1 flight per day.

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2h 15m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 15m
1 flight per day.
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1 stop route options with the same airline:

Duration

Via Detroit DTW
1 stop with Delta Air Lines. 1-2 flights per day.

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5h 40m

Via Detroit DTW
1 stop with Delta Air Lines.
5h 40m
1-2 flights per day.
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Via Baltimore BWI
1 stop with Southwest Airlines. 0-3 flights per day.

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5h 50m

Via Baltimore BWI
1 stop with Southwest Airlines.
5h 50m
0-3 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-2 flights per day.

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6h 28m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 28m
0-2 flights per day.
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Via Saint Louis STL
1 stop with Southwest Airlines.
Begins in 2/11

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6h 40m

Begins in 2/11
Via Saint Louis STL
1 stop with Southwest Airlines.
6h 40m
Begins in 2/11
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Chicago to Portland flights

With over 37 flights every week and 5 different airlines you have a wide range of options. You can fly non-stop to Portland (PWM) from Chicago (MDW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Detroit, Baltimore or any other of the 4 alternatives with connectiing airports.

Chicago to Portland with Southwest Airlines

You can fly non-stop every weekday with flights departing between 9:00 am and 7:00 pm. You can also catch a transit flight via Baltimore or Nashville.

With Delta Air Lines

If you fly from Chicago with Delta Air Lines you will do a stopover in Detroit, DTW before reaching Portland. This flight trip will take 5 hours and 40 minutes and you can fly every weekday with departures at 09 in the morning or 13 in the afternoon. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Midway International Airport to Portland International Jetport

The shortest flight time between MDW and PWM is 2 hours and 15 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 15m-898 miles (1445 km)
DTW Detroit5h 40m2h 31m899 miles (1446 km)
BWI Baltimore5h 50m2h 45m1066 miles (1715 km)
BNA Nashville6h 28m2h 10m1411 miles (2270 km)
STL Saint Louis6h 40m1h 20m1351 miles (2174 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.MDW-PWM flight routesChicago to Portland flight routes illustrated on a map.
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Chicago - Portland route map and flight paths
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You can fly non-stop from Chicago (MDW) to Portland (PWM) with Southwest Airlines. The flight takes approximately 2 hours and 15 minutes. If you travel with a connecting flight instead, for example via Detroit, the total flight time will be 5 hours and 40 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Delta Air Lines and Southwest Airlines is also an option.

The flight time between Chicago Midway (MDW) and Portland International Jetport (PWM) is approximately 2 hours and 15 minutes. The distance between the two airports is 899 miles (or 1446 kilometers).

Yes, you can fly non-stop to PWM from MDW with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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