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Cheap flights from Chicago to San Jose

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

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
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Economy Class
  • Economy Class
  • Business Class
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Chicago to San Jose flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Chicago (CHI) - San Jose (SJC) 2027-01-13 2027-01-16 352 USD 8 hours 55 minutes Direct 2026-09-27T23:10:09
Chicago (CHI) - San Jose (SJC) 2027-02-01 2027-02-15 356 USD 8 hours 45 minutes Direct 2026-10-01T10:23:17
Chicago (CHI) - San Jose (SJC) 2027-01-13 2027-01-15 365 USD 8 hours 45 minutes Direct 2026-09-27T23:09:25
Chicago (CHI) - San Jose (SJC) 2027-02-01 2027-02-04 375 USD 8 hours 50 minutes Direct 2026-09-28T16:57:25
Chicago (CHI) - San Jose (SJC) 2026-10-23 2026-10-26 390 USD 8 hours 35 minutes Direct 2026-09-29T16:27:13
Chicago (CHI) - San Jose (SJC) 2027-04-15 2027-04-17 430 USD 8 hours 45 minutes Direct 2026-09-27T01:59:39
Chicago (CHI) - San Jose (SJC) 2026-12-01 2026-12-04 448 USD 10 hours 25 minutes Connection 2026-09-28T16:56:38
Chicago (CHI) - San Jose (SJC) 2026-11-01 2026-11-04 450 USD 9 hours 5 minutes Direct 2026-09-27T01:41:42
Chicago (CHI) - San Jose (SJC) 2027-05-01 2027-05-04 465 USD 8 hours 45 minutes Direct 2026-09-28T16:56:39
Chicago (CHI) - San Jose (SJC) 2026-11-01 2026-11-05 475 USD 12 hours 50 minutes Direct 2026-10-03T13:28:05
Chicago (CHI) - San Jose (SJC) 2026-12-21 2027-01-03 485 USD 8 hours 50 minutes Direct 2026-09-27T18:09:30
Chicago (CHI) - San Jose (SJC) 2026-10-13 2026-10-20 493 USD 8 hours 45 minutes Direct 2026-09-27T12:26:53
Chicago (CHI) - San Jose (SJC) 2026-10-14 2026-10-17 598 USD 8 hours 35 minutes Direct 2026-09-27T12:34:34
Chicago (CHI) - San Jose (SJC) 2026-10-14 2026-10-16 634 USD 8 hours 35 minutes Direct 2026-09-27T12:31:51
Chicago (CHI) - San Jose (SJC) 2026-10-12 2026-10-15 711 USD 8 hours 40 minutes Direct 2026-09-27T19:19:34
Chicago (CHI) - San Jose (SJC) 2026-10-12 2026-10-16 711 USD 8 hours 40 minutes Direct 2026-09-27T19:19:34
Chicago (CHI) - San Jose (SJC) 2026-10-08 2026-10-12 724 USD 8 hours 35 minutes Direct 2026-09-30T02:48:27
Chicago (CHI) - San Jose (SJC) 2026-10-11 2026-10-15 739 USD 8 hours 35 minutes Direct 2026-09-27T13:45:46
Chicago (CHI) - San Jose (SJC) 2026-10-11 2026-10-16 739 USD 8 hours 35 minutes Direct 2026-09-27T13:45:46

Chicago to San Jose flight status

Flight Origin Destination Departure Arrival Equip
WN1646 Chicago (MDW) San Jose (SJC) 5:20 p.m. 6:45 p.m. B738
WN6124 Chicago (MDW) San Jose (SJC) 11 a.m. 12:20 p.m. B737
WN6691 Chicago (MDW) San Jose (SJC) 2 p.m. 4:25 p.m. B737
AZ530 Chicago (MDW) San Jose (SJC) 10:05 a.m. 11:10 a.m. 319

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