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Cheap Flights from Portland to Chicago by Month

On the Portland-Chicago route, airlines such as Southwest Airlines, American Airlines, Alaska Airlines, United Airlines operate flights. There are an average of 50 flights per week. Flight duration is usually
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← Find a return flight Chicago→Portland

Flight schedule Portland-Chicago

Time Flight Departure days
06:30 → 12:30 Southwest Airlines 5919 PDX-MDW M––TF–– 🔎
06:45 → 12:35 Southwest Airlines 5919 PDX-MDW –––––S– 🔎
06:50 → 12:45 Southwest Airlines 5919 PDX-MDW –TW–––– 🔎
07:00 → 13:02 United Airlines 1693 PDX-ORD MTWTFSS 🔎
07:20 → 13:20 Southwest Airlines 5919 PDX-MDW ––––––S 🔎
07:43 → 13:53 Alaska Airlines 324 PDX-ORD MTWTF–S 🔎
10:58 → 17:02 United Airlines 357 PDX-ORD –TW–––– 🔎
11:06 → 17:10 United Airlines 357 PDX-ORD MTWTFSS 🔎
12:09 → 18:19 Alaska Airlines 324 PDX-ORD –––––S– 🔎
13:32 → 19:30 American Airlines 2232 PDX-ORD MTWTFSS 🔎
14:14 → 20:19 United Airlines 321 PDX-ORD MTWTFS– 🔎
14:14 → 20:19 United Airlines 1660 PDX-ORD MTWTFS– 🔎
14:30 → 23:35 Southwest Airlines 1379 PDX-MDW ––––––S 🔎
22:24 → 04:45 Alaska Airlines 340 PDX-ORD MTWTF–S 🔎
23:50 → 05:56 United Airlines 1490 PDX-ORD MTWTFSS 🔎
23:54 → 06:00 American Airlines 1730 PDX-ORD MTWTFSS 🔎
23:59 → 06:05 United Airlines 1490 PDX-ORD ––––––S 🔎

← Other flights from Portland

← Other flights from Chicago