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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) 2027-02-01 2027-02-04 297 USD 15 hours 3 minutes Connection 2026-09-28T16:59:50
San Jose (SJC) - Chicago (CHI) 2026-11-01 2026-11-04 329 USD 13 hours 59 minutes Connection 2026-09-28T17:07:51
San Jose (SJC) - Chicago (CHI) 2026-12-01 2026-12-04 329 USD 15 hours 49 minutes Connection 2026-09-28T16:59:30
San Jose (SJC) - Chicago (CHI) 2026-10-19 2026-10-20 334 USD 27 hours 23 minutes Connection 2026-09-30T18:02:15
San Jose (SJC) - Chicago (CHI) 2027-05-05 2027-05-18 340 USD 14 hours 53 minutes Connection 2026-10-01T10:50:36
San Jose (SJC) - Chicago (CHI) 2027-04-18 2027-04-19 350 USD 13 hours 6 minutes Connection 2026-09-28T14:03:56
San Jose (SJC) - Chicago (CHI) 2026-11-03 2026-11-05 388 USD 12 hours 11 minutes Connection 2026-09-30T03:27:22
San Jose (SJC) - Chicago (CHI) 2026-10-19 2026-10-22 421 USD 14 hours 17 minutes Connection 2026-09-30T11:09:12
San Jose (SJC) - Chicago (CHI) 2027-01-01 2027-01-04 444 USD 13 hours 12 minutes Connection 2026-09-28T17:00:00
San Jose (SJC) - Chicago (CHI) 2027-07-01 2027-07-04 460 USD 13 hours 48 minutes Connection 2026-09-28T16:59:31
San Jose (SJC) - Chicago (CHI) 2026-10-15 2026-10-19 467 USD 14 hours 46 minutes Connection 2026-09-29T22:07:46
San Jose (SJC) - Chicago (CHI) 2027-04-01 2027-04-04 469 USD 16 hours 2 minutes Connection 2026-09-28T16:59:11
San Jose (SJC) - Chicago (CHI) 2026-11-08 2026-11-14 478 USD 9 hours 13 minutes Direct 2026-09-30T21:04:14
San Jose (SJC) - Chicago (CHI) 2026-10-01 2026-10-04 580 USD 31 hours 48 minutes Connection 2026-09-28T17:06:22
San Jose (SJC) - Chicago (CHI) 2026-10-01 2026-10-23 598 USD 9 hours 28 minutes Direct 2026-09-25T02:57:01
San Jose (SJC) - Chicago (CHI) 2026-10-18 2026-10-20 680 USD 9 hours 14 minutes Direct 2026-09-30T11:08:43
San Jose (SJC) - Chicago (CHI) 2026-10-04 2026-10-09 1006 USD 9 hours 18 minutes Direct 2026-09-29T19:14:49

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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