Portland International Jetport
Portland, United StatesPWM / KPWM
Regional airport · 43 direct destinations · 2 runways · longest runway 7,201 ft
57 °F · CloudySource: METAR observation via the NOAA Aviation Weather Center
Route
Portland → Chicago
PWM
PortlandPortland International Jetport
PortlandPortland International JetportMDWChicagoChicago Midway International Airport
ChicagoChicago Midway International Airport- Distance
- 893 mi
- Estimated flight time
- ~2h 20m
Chicago is currently 1 hour behind Portland.
Observed nonstop
How often does this route fly?
Frequency
Daily at most
On average around 1 flights a day, observed from October 2025 to September 2026.
- 1
- flights per day
- 1
- busiest month · Oct
- 2 hr 11 min
- measured flight time
- 6 / 12
- months seen
Through the year
Per day, month by month
- –Jan2026
- –Feb
- –Mar
- –Apr
- 1May
- 1Jun
- 1Jul
- 1Aug
- 1Sep
- 1Oct2025
- –Nov
- –Dec
In November 2025, December 2025, January 2026 we saw less traffic at Portland in general than usual; compare that month with care.
Airlines
Who flies it
Southwest Airlinessummer
Through the day
Departure times
Local time in Portland. Most departures between 06:00 and 09:00.
- 00:00
- 01:00
- 02:00
- 03:00
- 04:00
- 05:00
- 06:00
- 07:00
- 08:00
- 09:00
- 10:00
- 11:00
- 12:00
- 13:00
- 14:00
- 15:00
- 16:00
- 17:00
- 18:00
- 19:00
- 20:00
- 21:00
- 22:00
- 23:00
Through the week
By weekday
- 0.4Mon
- 0.4Tue
- 0.4Wed
- 0.4Thu
- 0.4Fri
- 0.4Sat
- 0.4Sun
Fleet
Aircraft observed
- Boeing 737-700B73746%
- Boeing 737 MAX 8B38M28%
- Boeing 737-800B73819%
- Bombardier Challenger 300CL302%
- Embraer Phenom 300E55P1%
All the numbers in a table
| Month | Per day | Seen | Airlines |
|---|---|---|---|
| January 2026 | Not seen in this month. | ||
| February 2026 | Not seen in this month. | ||
| March 2026 | Not seen in this month. | ||
| April 2026 | Not seen in this month. | ||
| May 2026 | 1 | 3 | – |
| June 2026 | 1 | 27 |
|
| July 2026 | 1 | 33 |
|
| August 2026 | 1 | 33 |
|
| September 2026 | 1 | 29 |
|
| October 2025 | 1 | 19 |
|
| November 2025 | Not seen in this month. | ||
| December 2025 | Not seen in this month. | ||
Airlines observed on this route
From observed callsign routes on PWM-MDW - not a booking guarantee.
About this route
- Domestic route: both airports are in the same country.
- The opposite direction has also been observed as a direct connection.
- Direct destinations observed from Portland: 43.
- Direct destinations observed from Chicago: 108.
The airports on this route
Chicago Midway International Airport
Chicago, United StatesMDW / KMDW
Major airport · 108 direct destinations · 4 runways · longest runway 6,522 ft
55 °F · CloudySource: METAR observation via the NOAA Aviation Weather Center
Alternative airports for this journey
Same journey, a different airport nearby - with an observed direct connection.
About the route from Portland to Chicago
The observed direct connection between Portland International Jetport (PWM) and Chicago Midway International Airport (MDW) covers approximately 893 mi. The estimated flight time is around 2h 20m. Southwest Airlines has been observed on this connection in the available route data.
Frequently asked questions about this route
- How far is Portland from Chicago by air?
- The great-circle distance between Portland International Jetport and Chicago Midway International Airport is approximately 893 mi.
- How long is the flight from Portland to Chicago?
- Based on the distance, the estimated flight time is about 2h 20m. This is an estimate, not a schedule.
- Is there a direct connection from Portland to Chicago?
- Yes, a direct connection between PWM and MDW has been observed in our route data.
- Which airlines have been observed on this route?
- In the available route data: Southwest Airlines.
- How often is there a flight from Portland to Chicago?
- On average around 1 flights a day, measured over twelve months (October 2025 to September 2026) in the flight archive, with 144 observed flights. Mainly Southwest Airlines. That is an observation, not a timetable.
- What is the current time difference between Portland and Chicago?
- Chicago is currently 1 hour behind Portland.
Where this data comes from
The route data comes from the flight archive (ADS-B, adsb.lol): which connections actually flew over the last twelve full months and who flew them, combined with our own airport, runway, and airline datasets. It is reference data about observed routes - not a current timetable and no claim about bookability.
The frequency and aircraft on this page come from the flight archive (ADS-B, 12 months, October 2025 to September 2026), summarized per route per month. We do not see every flight, so it is a floor, not a count.
Route data updated on October 11, 2026.