Direct (nonstop) flights from Portland to Chicago
1 airline flys nonstop from Portland International Jetport (PWM) to Chicago Midway International (MDW). It's 894 miles (1,439 km), about 2h 35m in the air. Operated by Southwest Airlines.
Southwest Airlines
Route data last updated: May 31, 2026
Airlines with non-stop flights
WN
Southwest Airlines
Alternative Routes
Other ways to fly from Portland to Chicago with one stop · direct emits 165 kg CO₂ per passenger
Looking for the return flight?
MDW → PWM: Flights from Chicago to PortlandOther direct flights from Portland
Direct flights from Chicago (MDW)
Frequently Asked Questions
How long is the direct flight from Portland to Chicago?
A nonstop flight from Portland (PWM) to Chicago (MDW) takes approximately 2 hours and 35 minutes. The distance is 894 miles (1,439 km).
Which airlines fly nonstop from Portland to Chicago?
Just Southwest Airlines.
Is there a nonstop flight from Portland to Chicago?
Yes. 1 airline: Southwest Airlines.
How far is Portland from Chicago?
The flight distance from Portland to Chicago is 894 miles (1,439 km), measured as the great-circle (shortest air) distance. That's roughly the same distance as London to Madrid.
What type of aircraft flies from Portland to Chicago?
At 2h 35m, this route typically uses narrow-body or mid-range jets — Boeing 737 MAX or Airbus A320neo. Varies by airline.
What is the carbon footprint of a flight from Portland to Chicago?
Roughly 165 kg CO2 per passenger one-way. That's about the same as driving 825 km.
Is the return flight from Chicago to Portland also nonstop?
Yes — nonstop flights run both ways. Flight time may differ slightly due to wind patterns.
When is the cheapest time to fly from Portland to Chicago?
Midweek flights (Tue/Wed) outside holiday peaks are usually cheapest. 3-6 weeks ahead is a good window for this route. Use "Check Prices" above to compare.
How early should I arrive at Portland International Jetport for this flight?
1.5-2 hours for domestic. Add more time during holidays or busy travel weekends.