Direct (non-stop) flights from Chicago to Portland

All flight schedules from Chicago Midway International , Illinois , USA to Portland International Jetport , Maine , USA. This route is operated by Southwest Airlines and the flight time is 2 hours and 25 minutes. The distance is 898 miles.

Monthly schedule
Week schedules
Airlines
Aircrafts
Price search
MDW Chicago Midway International
USA
Chicago , IL , USA
PWM Portland International Jetport
USA
Portland , ME , USA
CHANGE DIRECTION
Flight time
2h 25m
Flight distance
898mi, 1445km
Flights from Chicago to Portland route map
VIEW LARGER MAP
USA
USA
MDW
Chicago , IL
aircraft image
USA
USA
PWM
Portland , ME
Distance
898 miles · (1445 km)
CHANGE DIRECTION
Flight time
2 hours and 25 minutes

Airlines with direct flights from Chicago (MDW) to Portland (PWM)

  • Southwest Airlines
    S
    M
    T
    W
    T
    F
    S
    Begins in 2027-06-03
    Low-cost airline
    1 daily flight
FLIGHTS WITH STOPS
SELECT DATES & SHOW PRICES
MDW PWM
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MONTHLY
WN
WEEKLY

Chicago (MDW) to Portland (PWM) flight schedule

The monthly calendar shows every direct flight departure from Chicago Midway International (MDW) with all airlines. Click on a date to see a list of flights or search for the best prices.

Southwest

View return flights from PWM to MDW

Southwest Airlines flight schedule from Chicago to Portland

All weekly departures with Southwest Airlines. The week calendar shows every flight departure from Chicago (MDW) to Portland (PWM). Click on a blue date to see a list of flights.

Week 22 (May 31 - Jun 6)
  • Week 22 (May 31 - Jun 6)
  • Week 23 (Jun 7 - Jun 13)
  • Week 24 (Jun 14 - Jun 20)
  • Week 25 (Jun 21 - Jun 27)
  • Week 26 (Jun 28 - Jul 4)
  • Week 27 (Jul 5 - Jul 11)
  • Week 28 (Jul 12 - Jul 18)
  • Week 29 (Jul 19 - Jul 25)
  • Week 30 (Jul 26 - Aug 1)
  • Week 31 (Aug 2 - Aug 8)
Flight
Mon
May 31
Tue
Jun 1
Wed
Jun 2
Thu
Jun 3
Fri
Jun 4
Sat
Jun 5
Sun
Jun 6
WN4463
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12:55
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WN1083
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20:00
20:00
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19:15
Flight time
2h 15m - 2h 25m

US
Arriving at Portland Jetport (PWM) , Maine

Portland International Jetport (PWM) is a mid-sized airport in USA. You can fly to 30 destinations with 6 airlines in scheduled passenger traffic.

Show all flights from PWM

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Departing from Chicago Midway (MDW) , Illinois

Chicago Midway International (MDW) is a large airport in USA. You can fly to 94 destinations with 5 airlines in scheduled passenger traffic.

Show all flights from MDW

Airlines with alternative airports from Chicago to Portland

The airlines below are departing from or arriving to other airports in the same city or very close.

American Airlines
Oneworld
Chicago O Hare International Portland International Jetport
Duration
2 hours and 48 minutes
United
Star Alliance
Chicago O Hare International Portland International Jetport
Duration
2 hours and 55 minutes
Frontier Airlines
Chicago O Hare International Portland International Jetport
Duration
2 hours and 21 minutes
Show detailed flight schedule from ORD to PWM
American Airlines
Oneworld
Chicago O Hare International Portland International
Duration
4 hours and 56 minutes
Alaska Airlines
Oneworld
Chicago O Hare International Portland International
Duration
4 hours and 57 minutes
Spirit
Chicago O Hare International Portland International
Duration
4 hours and 19 minutes
United
Star Alliance
Chicago O Hare International Portland International
Duration
4 hours and 53 minutes
Virgin America
Chicago O Hare International Portland International
Duration
4 hours and 29 minutes
Aer Lingus
Chicago O Hare International Portland International
Duration
4 hours and 33 minutes
Show detailed flight schedule from ORD to PDX
Southwest
Chicago Midway International Portland International
Duration
4 hours and 45 minutes
Show detailed flight schedule from MDW to PDX

Chicago - Portland flight price statistics

$370
Approximate

The numbers are avarage prices found based on user searches for direct flights between Chicago Midway International and Portland International Jetport. Its calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.

N/A
Jan
N/A
Feb
N/A
Mar
N/A
Apr
$648
May
$321
Jun
$333
Jul
$333
Aug
$276
Sep
$242
Oct
N/A
Nov
N/A
Dec

Approximate prices for one round-trip flight from Chicago (MDW) to Portland (PWM). Graph is not to scale.

CLICK HERE FOR EXACT PRICES

Type of aircraft(s) on this route

Below is a list of aircraft types we have within our database with flights on this route. You can also see the aircrafts seat capacity together with classes.

Boeing 737MAX 8 Passenger
Southwest Airlines
Boeing 737MAX 8 Passenger illustration
Boeing 737MAX 8 Passenger illustration
175 seats
 (All economy)
ROUTE EXPLORING

Chicago Midway International - all destinations

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Chicago flight map

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Round trip
1 adult
Economy

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Frequently asked questions FAQ

  • The flight between Chicago (MDW) and Portland (PWM) typically takes about 2 hour and 15 minute.
  • The flight numbers are WN1083, WN1503 and WN4463.
  • From Chicago you will fly out from Chicago Midway International (MDW) and you will be landing at Portland International Jetport (PWM).
  • Boeing 737 flies this route operated by Southwest.
  • Southwest have non-stop flights to Portland.
VIEW IN
MAP EXPLORER Flights from Chicago to Portland route map
Non-stop flights from MDW to PWM
898 miles (1445 km) · 2 hours and 25 minutes
CHECK PRICES

Popular routes from Chicago

Southwest Airlines Southwest Airlines routes

Chicago (MDW) - Phoenix (PHX)

US

Chicago (MDW) - Orlando (MCO)

US

Chicago (MDW) - New York (LGA)

US

Chicago (MDW) - Las Vegas (LAS)

US

Chicago (MDW) - Denver (DEN)

US

For more destinations from Chicago with Southwest Airlines (WN), check out the Southwest Airlines route map .

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