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Flights from Chicago to Portland – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

MDW to PDX flights and routes map MDW to PDX – All flight route options from Chicago Midway International, Illinois, USA to Portland International, Oregon, USA. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 7 different transit flights. The shortest flight time is 4 hours and 25 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 PDX Portland , OR, USA
MDW
Chicago Midway
USAChicago, IL, USA
Portland
USAPortland, OR, USA
PDX
1 direct route found »
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10 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 2-3 flights per day.

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4h 25m

Southwest Airlines
Non-stop with Southwest Airlines.
4h 25m
2-3 flights per day.
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1 stop route options with the same airline:

Duration

Via Saint Louis STL
1 stop with Southwest Airlines.

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6h 15m

Via Saint Louis STL
1 stop with Southwest Airlines.
6h 15m
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Via Denver DEN
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 22/8

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7h 02m

Begins in 22/8
Via Denver DEN
1 stop with Frontier Airlines.
7h 02m
0-1 flights per day.
Begins in 22/8
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Via Minneapolis MSP
1 stop with Delta Air Lines. 0-1 flights per day.

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7h 07m

Via Minneapolis MSP
1 stop with Delta Air Lines.
7h 07m
0-1 flights per day.
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Via Denver DEN
1 stop with Southwest Airlines. 0-11 flights per day.

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7h 40m

Via Denver DEN
1 stop with Southwest Airlines.
7h 40m
0-11 flights per day.
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Via Detroit DTW
1 stop with Delta Air Lines. 0-1 flights per day.

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8h 36m

Via Detroit DTW
1 stop with Delta Air Lines.
8h 36m
0-1 flights per day.
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Via Sacramento SMF
1 stop with Southwest Airlines. 0-3 flights per day.

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8h 45m

Via Sacramento SMF
1 stop with Southwest Airlines.
8h 45m
0-3 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.

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9h 35m

Via Kansas City MCI
1 stop with Southwest Airlines.
9h 35m
0-1 flights per day.
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Via Minneapolis MSP
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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9h 43m

Only saturdays
Via Minneapolis MSP
1 stop with Southwest Airlines.
9h 43m
0-1 flights per day.
Only saturdays
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Via Albuquerque ABQ
1 stop with Southwest Airlines.
Begins in 5/10

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10h 20m

Begins in 5/10
Via Albuquerque ABQ
1 stop with Southwest Airlines.
10h 20m
Begins in 5/10
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1 stop route options with codeshare or different airlines:

Duration

Via Minneapolis MSP With Delta Air Lines & Alaska Airlines 0-1 flights per day.

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7h 39m

Via Minneapolis MSP
7h 39m
With Delta Air Lines & Alaska Airlines 0-1 flights per day.
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Chicago to Portland flights

With over 113 flights every week and 8 different airlines you have a wide range of options. You can fly non-stop to Portland (PDX) from Chicago (MDW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Saint Louis, Minneapolis or any other of the 7 alternatives with connectiing airports.

Chicago to Portland with Southwest Airlines

You can fly non-stop every weekday with flights departing from 7:00 am to 10:00 pm. You can also catch a transit flight via Saint Louis or Denver.

With Frontier Airlines

If you fly from Chicago with Frontier Airlines you will do a stopover in Denver, DEN before reaching Portland. This flight trip will take 7 hours and 2 minutes and you can fly every Monday or Friday with departures at 18:31 or 19:56.

Distance & flight times: Midway International Airport to Portland International

The shortest flight time between MDW and PDX is 4 hours and 20 minutes.

ViaTotal flight timeLayover timeDistance
Direct4h 20m-1756 miles (2825 km)
STL Saint Louis6h 15m3h 0m1965 miles (3162 km)
MSP Minneapolis7h 7m2h 56m1779 miles (2862 km)
DEN Denver7h 40m2h 40m1892 miles (3044 km)
DTW Detroit8h 36m2h 41m2187 miles (3519 km)
SMF Sacramento8h 45m2h 20m2277 miles (3664 km)
MCI Kansas City9h 35m2h 25m1891 miles (3043 km)
ABQ Albuquerque10h 20m2h 35m2241 miles (3606 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-PDX flight routesChicago to Portland flight routes illustrated on a map.
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You can fly non-stop from Chicago (MDW) to Portland (PDX) with Southwest Airlines. The flight takes approximately 4 hours and 20 minutes. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 6 hours and 15 minutes.

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

The flight time between Chicago Midway (MDW) and Portland International (PDX) is approximately 4 hours and 20 minutes. The distance between the two airports is 1779 miles (or 2862 kilometers).

Yes, you can fly non-stop to PDX 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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