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Cheap flights from Portland to Chicago

Find cheap Chicago to Portland flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Portland.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Portland to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Portland (PDX) - Chicago (CHI) 2024-05-14 2024-05-19 127 USD 21 hours 49 minutes Connection 2024-04-23T16:02:46
Portland (PDX) - Chicago (CHI) 2024-05-11 2024-05-19 148 USD 31 hours 0 minutes Connection 2024-04-22T23:20:52
Portland (PDX) - Chicago (CHI) 2024-05-14 2024-05-15 148 USD 16 hours 0 minutes Connection 2024-04-22T04:23:35
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-07 148 USD 16 hours 11 minutes Connection 2024-04-23T21:28:26
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-08 148 USD 23 hours 28 minutes Connection 2024-04-22T02:43:58
Portland (PDX) - Chicago (CHI) 2024-05-17 2024-05-21 151 USD 28 hours 53 minutes Connection 2024-04-22T22:42:49
Portland (PDX) - Chicago (CHI) 2024-05-14 2024-05-18 156 USD 28 hours 39 minutes Connection 2024-04-23T16:05:04
Portland (PDX) - Chicago (CHI) 2024-05-07 2024-05-11 158 USD 21 hours 0 minutes Connection 2024-04-23T16:52:45
Portland (PDX) - Chicago (CHI) 2024-05-08 2024-05-11 163 USD 21 hours 0 minutes Connection 2024-04-24T23:10:59
Portland (PDX) - Chicago (CHI) 2024-05-04 2024-05-08 167 USD 32 hours 39 minutes Connection 2024-04-24T15:54:25
Portland (PDX) - Chicago (CHI) 2024-05-06 2024-05-07 167 USD 16 hours 11 minutes Connection 2024-04-23T02:21:40
Portland (PDX) - Chicago (CHI) 2024-05-16 2024-05-21 167 USD 25 hours 32 minutes Connection 2024-04-25T15:54:18
Portland (PDX) - Chicago (CHI) 2024-05-14 2024-05-25 168 USD 16 hours 26 minutes Connection 2024-04-24T00:52:24
Portland (PDX) - Chicago (CHI) 2024-05-07 2024-05-08 169 USD 16 hours 11 minutes Connection 2024-04-23T04:43:54
Portland (PDX) - Chicago (CHI) 2024-05-07 2024-05-15 169 USD 16 hours 0 minutes Connection 2024-04-23T21:01:00
Portland (PDX) - Chicago (CHI) 2024-05-08 2024-05-12 169 USD 20 hours 55 minutes Connection 2024-04-23T23:49:07
Portland (PDX) - Chicago (CHI) 2024-05-08 2024-05-15 169 USD 16 hours 0 minutes Connection 2024-04-22T01:26:43
Portland (PDX) - Chicago (CHI) 2024-05-11 2024-05-15 169 USD 25 hours 11 minutes Connection 2024-04-23T05:38:54
Portland (PDX) - Chicago (CHI) 2024-05-15 2024-05-15 169 USD 16 hours 0 minutes Connection 2024-04-24T10:22:35
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-01 169 USD 16 hours 11 minutes Connection 2024-04-22T19:31:01
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-04 169 USD 16 hours 11 minutes Connection 2024-04-23T08:25:07
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-11 169 USD 16 hours 11 minutes Connection 2024-04-22T04:19:40
Portland (PDX) - Chicago (CHI) 2024-05-02 2024-05-08 171 USD 30 hours 58 minutes Connection 2024-04-23T04:29:17
Portland (PDX) - Chicago (CHI) 2024-05-07 2024-05-09 171 USD 16 hours 11 minutes Connection 2024-04-22T19:12:32
Portland (PDX) - Chicago (CHI) 2024-05-07 2024-05-10 171 USD 20 hours 55 minutes Connection 2024-04-23T23:47:57
Portland (PDX) - Chicago (CHI) 2024-05-08 2024-05-09 171 USD 16 hours 11 minutes Connection 2024-04-22T19:31:55
Portland (PDX) - Chicago (CHI) 2024-04-29 2024-05-01 171 USD 16 hours 11 minutes Connection 2024-04-22T18:50:46
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-02 171 USD 16 hours 11 minutes Connection 2024-04-22T17:17:09
Portland (PDX) - Chicago (CHI) 2024-04-30 2024-05-09 171 USD 16 hours 11 minutes Connection 2024-04-22T01:10:18
Portland (PDX) - Chicago (CHI) 2024-05-10 2024-05-15 172 USD 16 hours 0 minutes Connection 2024-04-22T01:05:46

Portland to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN3358 Portland (PDX) Chicago (MDW) 11 a.m. 12:45 p.m. B737
WN4366 Portland (PDX) Chicago (MDW) 9:15 p.m. 12:30 a.m. B737
DE1235 Portland (PDX) Chicago (MDW) 11:15 a.m. 1:20 p.m. 767
WN6831 Portland (PDX) Chicago (MDW) 2:15 p.m. 8:30 p.m. B737
K9167 Portland (PDX) Chicago (MDW) 2 p.m. 2:43 p.m. LJ35
AV719 Portland (PDX) Chicago (MDW) 7:40 a.m. 1:15 p.m. AT7
AH1159 Portland (PDX) Chicago (MDW) 7:05 a.m. 9:10 a.m. 738

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