Flights from Portland to Chicago (PDX to ORD)

Wed Oct 1st 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Wed Oct 1st 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Wed Oct 1st 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Thu Oct 2nd 2025 Spirit Airlines · NK 2079 Depart at 6:00am from Las Vegas (LAS) Fly for 3h 36m Arrive at 11:36am in Chicago (ORD)

Wed Oct 1st 2025 Spirit Airlines · NK 2653 Depart at 12:07pm from Portland (PDX) Fly for 2h 14m Arrive at 2:21pm in Las Vegas (LAS)

Wed Oct 1st 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Thu Oct 2nd 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Thu Oct 2nd 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Tue Oct 7th 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Tue Oct 7th 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Sat Oct 4th 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Sat Oct 4th 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Mon Oct 6th 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Mon Oct 6th 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Fri Oct 3rd 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Fri Oct 3rd 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Sun Oct 5th 2025 Spirit Airlines · NK 2083 Depart at 7:59pm from Portland (PDX) Fly for 2h 15m Arrive at 10:14pm in Las Vegas (LAS)

Sun Oct 5th 2025 Spirit Airlines · NK 2070 Depart at 11:10pm from Las Vegas (LAS) Fly for 3h 36m Arrive at 4:46am in Chicago (ORD)

Wed Oct 15th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Wed Oct 15th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Thu Oct 16th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Thu Oct 16th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 8th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Wed Oct 8th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Sat Oct 18th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Sat Oct 18th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Sun Oct 19th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Sun Oct 19th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Fri Oct 17th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Fri Oct 17th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 22nd 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Wed Oct 22nd 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Tue Oct 21st 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Tue Oct 21st 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Fri Oct 31st 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Fri Oct 31st 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Tue Oct 28th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Tue Oct 28th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Mon Oct 27th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Mon Oct 27th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 29th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Wed Oct 29th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Thu Oct 30th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Thu Oct 30th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Thu Oct 23rd 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Thu Oct 23rd 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Sat Oct 25th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Sat Oct 25th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Fri Oct 24th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Fri Oct 24th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 1st 2025 Hawaiian Airlines · HA 6397 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Wed Oct 1st 2025 Hawaiian Airlines · HA 6819 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6519 Depart at 2:31pm from Portland (PDX) Fly for 2h 35m Arrive at 5:06pm in San Diego (SAN)

Tue Oct 28th 2025 Hawaiian Airlines · HA 7493 Depart at 5:49pm from San Diego (SAN) Fly for 4h 10m Arrive at 11:59pm in Chicago (ORD)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6519 Depart at 2:31pm from Portland (PDX) Fly for 2h 35m Arrive at 5:06pm in San Diego (SAN)

Wed Oct 29th 2025 Hawaiian Airlines · HA 7493 Depart at 5:49pm from San Diego (SAN) Fly for 4h 10m Arrive at 11:59pm in Chicago (ORD)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6499 Depart at 7:00am from Portland (PDX) Fly for 2h 30m Arrive at 9:30am in San Diego (SAN)

Wed Oct 29th 2025 Hawaiian Airlines · HA 7478 Depart at 12:45pm from San Diego (SAN) Fly for 4h 10m Arrive at 6:55pm in Chicago (ORD)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6499 Depart at 7:00am from Portland (PDX) Fly for 2h 30m Arrive at 9:30am in San Diego (SAN)

Tue Oct 28th 2025 Hawaiian Airlines · HA 7478 Depart at 12:45pm from San Diego (SAN) Fly for 4h 10m Arrive at 6:55pm in Chicago (ORD)

Tue Oct 7th 2025 Hawaiian Airlines · HA 6307 Depart at 7:00am from Portland (PDX) Fly for 2h 32m Arrive at 9:32am in San Diego (SAN)

Tue Oct 7th 2025 Hawaiian Airlines · HA 6419 Depart at 12:20pm from San Diego (SAN) Fly for 4h 39m Arrive at 6:59pm in Chicago (ORD)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6228 Depart at 1:30pm from Portland (PDX) Fly for 1h 3m Arrive at 2:33pm in Seattle (SEA)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6817 Depart at 3:30pm from Seattle (SEA) Fly for 4h 9m Arrive at 9:39pm in Chicago (ORD)

Tue Oct 7th 2025 Hawaiian Airlines · HA 6414 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Wed Oct 8th 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6391 Depart at 7:35am from Portland (PDX) Fly for 1h 5m Arrive at 8:40am in Seattle (SEA)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6818 Depart at 10:15am from Seattle (SEA) Fly for 4h 12m Arrive at 4:27pm in Chicago (ORD)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6393 Depart at 1:30pm from Portland (PDX) Fly for 1h 3m Arrive at 2:33pm in Seattle (SEA)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6817 Depart at 3:30pm from Seattle (SEA) Fly for 4h 9m Arrive at 9:39pm in Chicago (ORD)

Tue Oct 14th 2025 Hawaiian Airlines · HA 6414 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Wed Oct 15th 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Sat Oct 4th 2025 Hawaiian Airlines · HA 6414 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Sun Oct 5th 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6391 Depart at 7:35am from Portland (PDX) Fly for 1h 5m Arrive at 8:40am in Seattle (SEA)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6818 Depart at 10:15am from Seattle (SEA) Fly for 4h 12m Arrive at 4:27pm in Chicago (ORD)

Sat Oct 4th 2025 Hawaiian Airlines · HA 6395 Depart at 7:41pm from Portland (PDX) Fly for 0h 54m Arrive at 8:35pm in Seattle (SEA)

Sun Oct 5th 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Fri Oct 3rd 2025 Hawaiian Airlines · HA 6374 Depart at 10:55pm from Portland (PDX) Fly for 4h 5m Arrive at 5:00am in Chicago (ORD)

Thu Oct 2nd 2025 Hawaiian Airlines · HA 6374 Depart at 10:55pm from Portland (PDX) Fly for 4h 5m Arrive at 5:00am in Chicago (ORD)

Sun Oct 26th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Sun Oct 26th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 1st 2025 Alaska Airlines · AS 1016 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Wed Oct 1st 2025 Alaska Airlines · AS 538 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Thu Oct 2nd 2025 Alaska Airlines · AS 376 Depart at 10:55pm from Portland (PDX) Fly for 4h 5m Arrive at 5:00am in Chicago (ORD)

Fri Oct 3rd 2025 Alaska Airlines · AS 376 Depart at 10:55pm from Portland (PDX) Fly for 4h 5m Arrive at 5:00am in Chicago (ORD)

Wed Oct 29th 2025 Alaska Airlines · AS 1312 Depart at 2:31pm from Portland (PDX) Fly for 2h 35m Arrive at 5:06pm in San Diego (SAN)

Wed Oct 29th 2025 Alaska Airlines · AS 1493 Depart at 5:49pm from San Diego (SAN) Fly for 4h 10m Arrive at 11:59pm in Chicago (ORD)

Fri Oct 31st 2025 Hawaiian Airlines · HA 6228 Depart at 1:30pm from Portland (PDX) Fly for 1h 3m Arrive at 2:33pm in Seattle (SEA)

Fri Oct 31st 2025 Hawaiian Airlines · HA 6817 Depart at 3:30pm from Seattle (SEA) Fly for 4h 9m Arrive at 9:39pm in Chicago (ORD)

Mon Oct 27th 2025 Hawaiian Airlines · HA 6567 Depart at 10:00pm from Portland (PDX) Fly for 1h 1m Arrive at 11:01pm in Seattle (SEA)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6669 Depart at 12:20am from Seattle (SEA) Fly for 4h 2m Arrive at 6:22am in Chicago (ORD)

Mon Oct 13th 2025 Hawaiian Airlines · HA 6414 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Tue Oct 14th 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Mon Oct 20th 2025 Hawaiian Airlines · HA 6414 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Tue Oct 21st 2025 Hawaiian Airlines · HA 6538 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Fri Oct 3rd 2025 Hawaiian Airlines · HA 6397 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Fri Oct 3rd 2025 Hawaiian Airlines · HA 6821 Depart at 3:59pm from Seattle (SEA) Fly for 4h 8m Arrive at 10:07pm in Chicago (ORD)

Mon Oct 27th 2025 Hawaiian Airlines · HA 6519 Depart at 2:31pm from Portland (PDX) Fly for 2h 35m Arrive at 5:06pm in San Diego (SAN)

Mon Oct 27th 2025 Hawaiian Airlines · HA 7493 Depart at 5:49pm from San Diego (SAN) Fly for 4h 10m Arrive at 11:59pm in Chicago (ORD)

Mon Oct 20th 2025 Hawaiian Airlines · HA 6247 Depart at 1:25pm from Portland (PDX) Fly for 1h 10m Arrive at 2:35pm in Seattle (SEA)

Mon Oct 20th 2025 Hawaiian Airlines · HA 6819 Depart at 5:50pm from Seattle (SEA) Fly for 4h 9m Arrive at 11:59pm in Chicago (ORD)

Fri Oct 3rd 2025 Hawaiian Airlines · HA 6397 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Fri Oct 3rd 2025 Hawaiian Airlines · HA 6819 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Thu Oct 2nd 2025 Hawaiian Airlines · HA 6397 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Thu Oct 2nd 2025 Hawaiian Airlines · HA 6819 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Tue Oct 7th 2025 Alaska Airlines · AS 3408 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Wed Oct 8th 2025 Alaska Airlines · AS 384 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Sat Oct 4th 2025 Alaska Airlines · AS 3408 Depart at 10:00pm from Portland (PDX) Fly for 1h 4m Arrive at 11:04pm in Seattle (SEA)

Sun Oct 5th 2025 Alaska Airlines · AS 384 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Sat Oct 4th 2025 Alaska Airlines · AS 2113 Depart at 7:41pm from Portland (PDX) Fly for 0h 54m Arrive at 8:35pm in Seattle (SEA)

Sun Oct 5th 2025 Alaska Airlines · AS 384 Depart at 12:17am from Seattle (SEA) Fly for 4h 7m Arrive at 6:24am in Chicago (ORD)

Tue Oct 28th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Wed Oct 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Sat Oct 4th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Sat Oct 25th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Mon Oct 27th 2025 Hawaiian Airlines · HA 6499 Depart at 7:00am from Portland (PDX) Fly for 2h 30m Arrive at 9:30am in San Diego (SAN)

Mon Oct 27th 2025 Hawaiian Airlines · HA 7478 Depart at 12:45pm from San Diego (SAN) Fly for 4h 10m Arrive at 6:55pm in Chicago (ORD)

Sat Oct 4th 2025 Alaska Airlines · AS 324 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Tue Oct 28th 2025 Alaska Airlines · AS 324 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Wed Oct 29th 2025 Alaska Airlines · AS 324 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Fri Oct 31st 2025 United Airlines · UA 534 Depart at 10:52am from Portland (PDX) Fly for 4h 2m Arrive at 4:54pm in Chicago (ORD)

Fri Oct 31st 2025 United Airlines · UA 2635 Depart at 7:00am from Portland (PDX) Fly for 4h 2m Arrive at 1:02pm in Chicago (ORD)

Fri Oct 31st 2025 Alaska Airlines · AS 1407 Depart at 1:30pm from Portland (PDX) Fly for 1h 3m Arrive at 2:33pm in Seattle (SEA)

Fri Oct 31st 2025 Alaska Airlines · AS 410 Depart at 3:30pm from Seattle (SEA) Fly for 4h 9m Arrive at 9:39pm in Chicago (ORD)

Fri Oct 3rd 2025 Alaska Airlines · AS 1016 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Fri Oct 3rd 2025 Alaska Airlines · AS 941 Depart at 3:59pm from Seattle (SEA) Fly for 4h 8m Arrive at 10:07pm in Chicago (ORD)

Fri Oct 3rd 2025 Alaska Airlines · AS 1016 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Fri Oct 3rd 2025 Alaska Airlines · AS 364 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Thu Oct 2nd 2025 Alaska Airlines · AS 1016 Depart at 1:24pm from Portland (PDX) Fly for 1h 2m Arrive at 2:26pm in Seattle (SEA)

Thu Oct 2nd 2025 Alaska Airlines · AS 538 Depart at 5:55pm from Seattle (SEA) Fly for 4h 8m Arrive at 12:03am in Chicago (ORD)

Mon Oct 20th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Mon Oct 20th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Sat Oct 11th 2025 Spirit Airlines · NK 786 Depart at 2:35pm from Portland (PDX) Fly for 2h 16m Arrive at 4:51pm in Las Vegas (LAS)

Sat Oct 11th 2025 Spirit Airlines · NK 184 Depart at 5:56pm from Las Vegas (LAS) Fly for 3h 47m Arrive at 11:43pm in Chicago (ORD)

Wed Oct 29th 2025 United Airlines · UA 2635 Depart at 7:00am from Portland (PDX) Fly for 4h 2m Arrive at 1:02pm in Chicago (ORD)

Tue Oct 28th 2025 United Airlines · UA 534 Depart at 10:52am from Portland (PDX) Fly for 4h 2m Arrive at 4:54pm in Chicago (ORD)

Tue Oct 28th 2025 United Airlines · UA 2635 Depart at 7:00am from Portland (PDX) Fly for 4h 2m Arrive at 1:02pm in Chicago (ORD)

Sat Oct 4th 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Sat Oct 18th 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Wed Oct 15th 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Wed Oct 15th 2025 United Airlines · UA 534 Depart at 10:46am from Portland (PDX) Fly for 4h 8m Arrive at 4:54pm in Chicago (ORD)

Tue Oct 21st 2025 United Airlines · UA 534 Depart at 10:46am from Portland (PDX) Fly for 4h 8m Arrive at 4:54pm in Chicago (ORD)

Wed Oct 8th 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Tue Oct 21st 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Sat Oct 25th 2025 United Airlines · UA 534 Depart at 10:46am from Portland (PDX) Fly for 4h 8m Arrive at 4:54pm in Chicago (ORD)

Wed Oct 22nd 2025 United Airlines · UA 534 Depart at 10:46am from Portland (PDX) Fly for 4h 8m Arrive at 4:54pm in Chicago (ORD)

Wed Oct 22nd 2025 United Airlines · UA 2145 Depart at 7:00am from Portland (PDX) Fly for 4h 8m Arrive at 1:08pm in Chicago (ORD)

Sat Oct 4th 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Sat Oct 18th 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Wed Oct 1st 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Sat Oct 11th 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Wed Oct 15th 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Tue Oct 7th 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Tue Oct 21st 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Wed Oct 22nd 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Thu Oct 2nd 2025 United Airlines · UA 2074 Depart at 8:35am from Portland (PDX) Fly for 4h 8m Arrive at 2:43pm in Chicago (ORD)

Thu Oct 2nd 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Fri Oct 3rd 2025 United Airlines · UA 1850 Depart at 2:15pm from Portland (PDX) Fly for 4h 10m Arrive at 8:25pm in Chicago (ORD)

Sun Oct 5th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 4m Arrive at 1:04pm in Chicago (ORD)

Thu Oct 30th 2025 United Airlines · UA 2635 Depart at 7:00am from Portland (PDX) Fly for 4h 2m Arrive at 1:02pm in Chicago (ORD)