Nonstop flights from Chicago to Portland

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

ORDPWM

Routes

2 airport pairs

When they leave

Chicago time

8:05a7:13pFirst departure 8:05 AM, last 7:13 PM

Three in the morning, 8:05 AM to 11:58 AM, then two in the afternoon, 1:59 PM to 2:00 PM, then five in the evening, 6:08 PM to 7:13 PM.

Every flight

Earliest first

8:05 AM→11:38 AMORD to PWMAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Daily
11:00 AM→2:31 PMORD to PWMUnited AirlinesBoeing 737 MAX 8Daily
11:58 AM→3:27 PMORD to PWMAmerican AirlinesUntil Dec 1, back Mar 4, 2027Airbus A319Sat
1:59 PM→5:32 PMORD to PWMAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Mon, Tue, Wed, Thu, Fri, Sun
2:00 PM→5:42 PMORD to PWMUnited AirlinesEmbraer 175Tue
6:08 PM→9:41 PMORD to PWMUnited AirlinesBoeing 737 MAX 8Daily
6:10 PM→9:35 PMMDW to PWMSouthwest AirlinesUntil Oct 30Boeing 737-700Mon, Thu, Fri
6:30 PM→9:45 PMMDW to PWMSouthwest AirlinesUntil Oct 30Boeing 737-700Sun
6:50 PM→10:05 PMMDW to PWMSouthwest AirlinesUntil Oct 30Boeing 737-700Tue, Wed, Sat
7:13 PM→10:48 PMORD to PWMAmerican AirlinesUntil Dec 1, back Mar 4, 2027Embraer 175Daily

Schedules last checked Sep 19, 2026. Times are local.

Flying from Chicago to Portland

American Airlines flies most often, 3 times a day on the Embraer 175 and Airbus A319. United Airlines flies 2 to 3 times a day on the Boeing 737 MAX 8 and Embraer 175. Southwest Airlines flies daily on the Boeing 737-700.

Flights run every day of the week, 7 on Tuesdays and 6 on the other days. The first arrival in Portland is at 11:38 AM and the last at 10:48 PM.

ORD to PWM is the busiest airport pair, with 36 flights a week, then MDW to PWM with 7.

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

Flying back, Portland to Chicago has 49 nonstop flights a week.

Return flights

Portland to ChicagoView

Find the cheapest day to fly from Chicago to Portland.

Schedules as of Oct 9, 2026.