Nonstop flights from Portland to Chicago

4 airlines fly from Portland (PDX) to 2 Chicago airports (ORD and MDW), with up to 13 flights a day.

PDXORD

Routes

2 airport pairs

When they leave

Portland time

5:59a11:40pFirst departure 5:59 AM, last 11:40 PM

Nine in the morning, 5:59 AM to 11:35 AM, then two in the afternoon, 12:24 PM to 2:25 PM, then five in the evening, 10:40 PM to 11:40 PM.

Every flight

Earliest first

5:59 AM→12:12 PMPDX to ORDAmerican AirlinesBoeing 737Daily
6:15 AM→12:10 PMPDX to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Tue, Wed, Thu, Fri
7:00 AM→1:13 PMPDX to ORDUnited AirlinesBoeing 737Daily
7:00 AM→1:13 PMPDX to ORDAlaska AirlinesBoeing 737 MAX 9Daily
7:35 AM→1:35 PMPDX to MDWSouthwest AirlinesBoeing 737Sat
8:17 AM→2:30 PMPDX to ORDUnited AirlinesBoeing 737Tue
10:35 AM→4:48 PMPDX to ORDUnited AirlinesBoeing 737 MAX 9Tue
10:46 AM→5:00 PMPDX to ORDUnited AirlinesAirbus A321neoMon, Wed, Thu, Fri, Sat, Sun
10:55 AM→4:55 PMPDX to MDWSouthwest AirlinesBoeing 737Sun
11:35 AM→5:35 PMPDX to MDWSouthwest AirlinesBoeing 737Mon, Thu, Fri
12:24 PM→6:45 PMPDX to ORDAmerican AirlinesBoeing 737Daily
2:25 PM→8:38 PMPDX to ORDUnited AirlinesBoeing 737Daily
10:40 PM→4:45 AM⁺¹PDX to ORDUnited AirlinesBoeing 737Daily
10:59 PM→5:00 AM⁺¹PDX to ORDAlaska AirlinesBoeing 737Daily
11:30 PM→5:25 AM⁺¹PDX to MDWSouthwest AirlinesBoeing 737 MAX 8Daily
11:34 PM→5:32 AM⁺¹PDX to ORDAmerican AirlinesBoeing 737Daily
11:40 PM→5:45 AM⁺¹PDX to ORDUnited AirlinesBoeing 737Mon, Wed, Thu, Fri, Sat, Sun

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

Flying from Portland to Chicago

United Airlines flies most often, 5 times a day on the Boeing 737, Airbus A321neo and Boeing 737 MAX 9. American Airlines flies 3 times a day on the Boeing 737. Southwest Airlines flies 2 to 3 times a day on the Boeing 737 and 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, 13 on Mondays, Thursdays and Fridays and 12 on the other days. The first arrival in Chicago is at 12:10 PM and the last at 5:45 AM the next day.

PDX to ORD is the busiest airport pair, with 70 flights a week, then PDX to MDW with 17.

Flying back, Chicago to Portland has 89 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.