1. Home
  2. Flights Search
  3. Flights from Oakland to Chicago

Cheap flights from Oakland to Chicago

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

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

Oakland to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Oakland (OAK) - Chicago (CHI) 2024-08-31 2024-09-11 235 USD 18 hours 42 minutes Connection 2024-04-24T16:55:42
Oakland (OAK) - Chicago (CHI) 2024-06-04 2024-06-25 240 USD 22 hours 38 minutes Connection 2024-04-23T13:37:45
Oakland (OAK) - Chicago (CHI) 2024-09-07 2024-09-10 240 USD 20 hours 21 minutes Connection 2024-04-23T14:58:54
Oakland (OAK) - Chicago (CHI) 2024-09-07 2024-09-14 240 USD 20 hours 21 minutes Connection 2024-04-23T08:01:34
Oakland (OAK) - Chicago (CHI) 2024-09-07 2024-09-21 240 USD 20 hours 21 minutes Connection 2024-04-25T22:14:02
Oakland (OAK) - Chicago (CHI) 2024-08-10 2024-08-24 240 USD 17 hours 25 minutes Connection 2024-04-24T01:22:13
Oakland (OAK) - Chicago (CHI) 2024-08-10 2024-08-31 240 USD 20 hours 12 minutes Connection 2024-04-24T05:35:28
Oakland (OAK) - Chicago (CHI) 2024-08-17 2024-08-28 240 USD 21 hours 8 minutes Connection 2024-04-24T02:48:31
Oakland (OAK) - Chicago (CHI) 2024-09-21 2024-09-25 240 USD 20 hours 11 minutes Connection 2024-04-25T13:11:40
Oakland (OAK) - Chicago (CHI) 2024-09-28 2024-10-01 240 USD 20 hours 59 minutes Connection 2024-04-24T21:30:21
Oakland (OAK) - Chicago (CHI) 2024-09-28 2024-10-02 240 USD 22 hours 1 minutes Connection 2024-04-25T16:18:03
Oakland (OAK) - Chicago (CHI) 2024-09-28 2024-10-05 240 USD 18 hours 36 minutes Connection 2024-04-25T01:38:20
Oakland (OAK) - Chicago (CHI) 2024-09-28 2024-10-08 240 USD 21 hours 24 minutes Connection 2024-04-24T19:45:51
Oakland (OAK) - Chicago (CHI) 2024-10-08 2024-10-15 241 USD 20 hours 14 minutes Connection 2024-04-25T03:52:25
Oakland (OAK) - Chicago (CHI) 2024-05-14 2024-05-15 241 USD 19 hours 12 minutes Connection 2024-04-24T00:14:56
Oakland (OAK) - Chicago (CHI) 2024-11-02 2024-11-07 242 USD 16 hours 3 minutes Connection 2024-04-23T23:34:26
Oakland (OAK) - Chicago (CHI) 2024-11-02 2024-11-12 242 USD 16 hours 38 minutes Connection 2024-04-26T00:53:58
Oakland (OAK) - Chicago (CHI) 2024-12-04 2024-12-07 242 USD 16 hours 43 minutes Connection 2024-04-26T01:58:58
Oakland (OAK) - Chicago (CHI) 2024-12-04 2024-12-10 242 USD 18 hours 23 minutes Connection 2024-04-24T03:02:02
Oakland (OAK) - Chicago (CHI) 2024-07-06 2024-07-14 242 USD 16 hours 31 minutes Connection 2024-04-25T19:49:44
Oakland (OAK) - Chicago (CHI) 2024-07-06 2024-07-21 242 USD 16 hours 31 minutes Connection 2024-04-25T15:13:05
Oakland (OAK) - Chicago (CHI) 2024-07-06 2024-07-28 242 USD 16 hours 31 minutes Connection 2024-04-25T18:45:37
Oakland (OAK) - Chicago (CHI) 2024-10-12 2024-10-15 242 USD 19 hours 34 minutes Connection 2024-04-25T00:00:23
Oakland (OAK) - Chicago (CHI) 2024-10-16 2024-10-19 242 USD 16 hours 39 minutes Connection 2024-04-25T16:19:18
Oakland (OAK) - Chicago (CHI) 2024-11-20 2024-12-03 242 USD 20 hours 14 minutes Connection 2024-04-24T01:57:28
Oakland (OAK) - Chicago (CHI) 2024-11-20 2024-12-04 242 USD 20 hours 42 minutes Connection 2024-04-24T13:30:40
Oakland (OAK) - Chicago (CHI) 2024-10-23 2024-10-30 242 USD 20 hours 14 minutes Connection 2024-04-24T21:29:31
Oakland (OAK) - Chicago (CHI) 2024-10-26 2024-10-30 242 USD 19 hours 44 minutes Connection 2024-04-25T04:06:31
Oakland (OAK) - Chicago (CHI) 2024-10-29 2024-11-02 242 USD 21 hours 6 minutes Connection 2024-04-23T03:17:09
Oakland (OAK) - Chicago (CHI) 2024-10-29 2024-11-14 242 USD 16 hours 59 minutes Connection 2024-04-25T02:42:45

Oakland to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN4297 Oakland (OAK) Chicago (MDW) 3:10 p.m. 5:05 p.m. B738
WN1788 Oakland (OAK) Chicago (MDW) 10:55 a.m. 2:10 p.m. B737
WN6018 Oakland (OAK) Chicago (MDW) 3:30 p.m. 4:30 p.m. B738
FO187 Oakland (OAK) Chicago (MDW) 8:35 a.m. 10:30 a.m. CR2

Popular Flights Searchs

  • Domestic Destinations
  • International Destinations