Flights from San Jose to Chicago

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12+
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under 2 years
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Outbound flight: 03/15/21
18:45 SJC
06:46 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 03/29/21
22:11 CHI
08:24 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
American Airlines
$251
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Outbound flight: 03/15/21
18:45 SJC
06:46 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 03/29/21
22:11 CHI
08:24 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
American Airlines
$251
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Outbound flight: 02/06/21
10:20 SJC
23:40 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
2 Stopovers
Alaska Airlines
Return flight: 02/20/21
14:05 CHI
19:33 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
Alaska Airlines
$270
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Outbound flight: 02/06/21
10:20 SJC
23:40 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
2 Stopovers
Alaska Airlines
Return flight: 02/20/21
07:20 CHI
10:09 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
direct
Alaska Airlines
$270
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Outbound flight: 02/06/21
10:20 SJC
23:40 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
2 Stopovers
Alaska Airlines
Return flight: 02/20/21
07:20 CHI
10:09 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
direct
Alaska Airlines
$270
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Outbound flight: 02/06/21
18:55 SJC
15:15 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Alaska Airlines
Return flight: 02/20/21
06:00 CHI
12:35 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
Alaska Airlines
$278
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Outbound flight: 02/06/21
18:55 SJC
15:15 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Alaska Airlines
Return flight: 02/20/21
06:00 CHI
12:35 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
Alaska Airlines
$278
Check
Outbound flight: 05/18/21
22:55 SJC
05:02 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 06/01/21
15:00 CHI
19:52 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
American Airlines
$290
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Outbound flight: 05/18/21
07:41 SJC
13:48 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
Return flight: 06/01/21
15:00 CHI
19:52 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
American Airlines
$290
Check
Outbound flight: 05/18/21
08:53 SJC
17:26 CHI
San Jose International Airport, CA
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
Return flight: 06/01/21
13:30 CHI
18:22 SJC
Chicago-IL all Airports (ORD, MDW, RFD)
San Jose International Airport, CA
1 Stopover
American Airlines
$290
Check
Prices based on recent searches, subject to last-minute changes
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Flight information San Jose - Chicago
Alternative flight routes
Cheap direct flights
Flight details San Jose - Chicago
  • Flight duration: min. 04:00 / max. 07:50
  • Distance: 2963 km
  • Flights per week: 61
  • Return flight duration: min. 04:42 / max. 09:50
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.