Nonstop flights from Portland to Chicago

3 airlines fly from Portland (PWM) to 2 Chicago airports (ORD and MDW), with up to 7 flights a day.

PWMORD

Routes

2 airport pairs

When they leave

Portland time

6:03a6:09pFirst departure 6:03 AM, last 6:09 PM

Three in the morning, 6:03 AM to 9:08 AM, then three in the afternoon, 12:09 PM to 4:07 PM, then three in the evening, 5:03 PM to 6:09 PM.

Every flight

Earliest first

6:03 AM→8:00 AMPWM to ORDUnited AirlinesBoeing 737 MAX 8Daily
7:40 AM→9:43 AMPWM to ORDUnited AirlinesEmbraer 175Daily
7:40 AM→9:10 AMPWM to MDWSouthwest AirlinesUntil Oct 30Boeing 737-700Mon, Tue, Wed, Thu, Fri
9:08 AM→11:07 AMPWM to ORDAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Daily
12:09 PM→2:09 PMPWM to ORDAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Daily
3:45 PM→5:20 PMPWM to MDWSouthwest AirlinesUntil Oct 30Boeing 737 MAX 8Sat
4:07 PM→6:14 PMPWM to ORDAmerican AirlinesUntil Dec 1, back Mar 4, 2027Airbus A319Sat
5:03 PM→7:00 PMPWM to ORDUnited AirlinesBoeing 737 MAX 9Daily
5:15 PM→6:45 PMPWM to MDWSouthwest AirlinesUntil Oct 30Boeing 737Sun
6:09 PM→8:30 PMPWM to ORDAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Mon, Tue, Wed, Thu, Fri, Sun

Schedules last checked Oct 7, 2026. Times are local.

Flying from Portland to Chicago

American Airlines flies 3 times a day on the Embraer 175 and Airbus A319. United Airlines flies 3 times a day on the Boeing 737 MAX 8, Boeing 737 MAX 9 and Embraer 175. Southwest Airlines flies daily on the Boeing 737, Boeing 737 MAX 8 and Boeing 737-700.

There are 7 flights every day of the week. The first arrival in Chicago is at 8:00 AM and the last at 8:30 PM.

PWM to ORD is the busiest airport pair, with 42 flights a week, then PWM to MDW with 7.

On PWM to ORD, American Airlines flies it until Dec 1 and is back on Mar 4, 2027. On PWM to MDW, Southwest Airlines flies it until Oct 30.

Flying back, Chicago to Portland has 43 nonstop flights a week.

Return flights

Chicago to PortlandView

Find the cheapest day to fly from Portland to Chicago.

Schedules as of Oct 9, 2026.