Nonstop flights from Chicago to Portland

4 airlines fly from 2 Chicago airports (ORD and MDW) to Portland (PDX), with up to 14 flights a day.

ORDPDX

Routes

2 airport pairs

When they leave

Chicago time

7:00a10:15pFirst departure 7:00 AM, last 10:15 PM

Five in the morning, 7:00 AM to 10:40 AM, then five in the afternoon, 12:10 PM to 4:15 PM, then six in the evening, 6:30 PM to 10:15 PM.

Every flight

Earliest first

7:00 AM→9:34 AMORD to PDXUnited AirlinesAirbus A321neoDaily
7:20 AM→9:45 AMORD to PDXAlaska AirlinesBoeing 737Daily
8:00 AM→10:36 AMORD to PDXAmerican AirlinesAirbus A321Mon, Tue
9:00 AM→11:38 AMORD to PDXUnited AirlinesAirbus A321neoDaily
9:00 AM→11:34 AMORD to PDXAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
10:40 AM→12:50 PMMDW to PDXSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri
12:10 PM→2:40 PMORD to PDXAmerican AirlinesAirbus A321Mon, Tue
1:30 PM→3:57 PMORD to PDXUnited AirlinesBoeing 737Daily
2:12 PM→4:47 PMORD to PDXAlaska AirlinesBoeing 737 MAX 9Daily
3:25 PM→6:00 PMORD to PDXAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
4:15 PM→6:47 PMORD to PDXUnited AirlinesBoeing 737Daily
6:30 PM→8:45 PMMDW to PDXSouthwest AirlinesBoeing 737 MAX 8Daily
7:55 PM→10:30 PMORD to PDXUnited AirlinesBoeing 737Daily
8:50 PM→11:05 PMMDW to PDXSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sat
9:20 PM→11:30 PMMDW to PDXSouthwest AirlinesBoeing 737 MAX 8Sun
9:30 PM→11:59 PMORD to PDXAmerican AirlinesBoeing 737Daily
10:15 PM→12:50 AM⁺¹ORD to PDXAmerican AirlinesBoeing 737Mon, Tue

Schedules last checked Sep 21, 2026. Times are local.

Flying from Chicago to Portland

United Airlines flies most often, 5 times a day on the Boeing 737 and Airbus A321neo. American Airlines flies 3 to 4 times a day on the Boeing 737 and Airbus A321. Southwest Airlines flies 2 to 3 times a day on the Boeing 737 MAX 8. Alaska Airlines flies twice a day on the Boeing 737 and Boeing 737 MAX 9.

Flights run every day of the week, from 12 on Wednesdays, Saturdays and Sundays to 14 on Mondays. The first arrival in Portland is at 9:34 AM and the last at 12:50 AM the next day.

ORD to PDX is the busiest airport pair, with 72 flights a week, then MDW to PDX with 17.

Flying back, Portland to Chicago has 87 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.