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Cheap flights from San Jose to Chicago

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

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

San Jose to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
San Jose (SJC) - Chicago (CHI) 2026-12-16 2026-12-18 335 USD 22 hours 42 minutes Connection 2026-11-14T23:09:22
San Jose (SJC) - Chicago (CHI) 2026-12-30 2026-12-31 379 USD 15 hours 40 minutes Connection 2026-11-12T00:16:13
San Jose (SJC) - Chicago (CHI) 2026-12-10 2026-12-18 404 USD 16 hours 1 minutes Connection 2026-11-14T11:43:04
San Jose (SJC) - Chicago (CHI) 2027-08-01 2027-08-04 409 USD 17 hours 47 minutes Connection 2026-11-14T21:23:17
San Jose (SJC) - Chicago (CHI) 2027-07-01 2027-07-04 448 USD 14 hours 15 minutes Connection 2026-11-10T00:09:48
San Jose (SJC) - Chicago (CHI) 2026-12-12 2026-12-19 494 USD 16 hours 6 minutes Connection 2026-11-12T07:30:42
San Jose (SJC) - Chicago (CHI) 2026-12-30 2027-01-03 536 USD 9 hours 18 minutes Direct 2026-11-10T15:52:06
San Jose (SJC) - Chicago (CHI) 2026-12-25 2026-12-31 545 USD 9 hours 18 minutes Direct 2026-11-12T11:22:20
San Jose (SJC) - Chicago (CHI) 2026-12-25 2026-12-30 552 USD 9 hours 26 minutes Direct 2026-11-12T00:29:42
San Jose (SJC) - Chicago (CHI) 2026-11-30 2026-12-03 572 USD 14 hours 24 minutes Connection 2026-11-13T11:27:49
San Jose (SJC) - Chicago (CHI) 2026-11-19 2026-11-22 627 USD 18 hours 9 minutes Connection 2026-11-12T18:51:18
San Jose (SJC) - Chicago (CHI) 2026-11-27 2026-11-30 700 USD 9 hours 14 minutes Direct 2026-11-11T00:37:47
San Jose (SJC) - Chicago (CHI) 2026-12-19 2027-01-03 759 USD 9 hours 18 minutes Direct 2026-11-12T23:12:07
San Jose (SJC) - Chicago (CHI) 2026-11-24 2026-11-28 863 USD 9 hours 2 minutes Direct 2026-11-13T05:19:03
San Jose (SJC) - Chicago (CHI) 2026-11-17 2026-11-17 869 USD 12 hours 56 minutes Connection 2026-11-13T21:30:25
San Jose (SJC) - Chicago (CHI) 2026-11-16 2026-11-19 1055 USD 9 hours 26 minutes Direct 2026-11-12T18:50:51
San Jose (SJC) - Chicago (CHI) 2026-11-18 2026-11-21 1079 USD 9 hours 5 minutes Direct 2026-11-15T04:30:20

San Jose to Chicago flight status

Flight Origin Destination Departure Arrival Equip
BA6697 San Jose (SJC) Chicago (ORD) 7:18 p.m. 7:53 p.m. A320
AA753 San Jose (SJC) Chicago (ORD) 9:45 a.m. 5:15 p.m. A321
BA5398 San Jose (SJC) Chicago (ORD) 6:05 p.m. 8:30 p.m. None
BA6681 San Jose (SJC) Chicago (ORD) 5:30 p.m. 7:19 p.m. None
AS6242 San Jose (SJC) Chicago (ORD) 7:44 p.m. 9:22 p.m.
QR2870 San Jose (SJC) Chicago (ORD) 1:24 p.m. 5:14 p.m. None
IB4293 San Jose (SJC) Chicago (ORD) 10:12 a.m. 11:36 a.m. None
IB4160 San Jose (SJC) Chicago (ORD) 10:55 a.m. 12:14 p.m. ERD
BA6870 San Jose (SJC) Chicago (ORD) 5:23 p.m. 6:39 p.m. None
XO751 San Jose (SJC) Chicago (ORD) 8:30 a.m. 1:54 p.m. C750
WQ2514 San Jose (SJC) Chicago (ORD) None None B734
WQ2554 San Jose (SJC) Chicago (ORD) None None B737

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