Take off on cheap flights from San Jose to Chicago, your adventure starts now!

Find cheap airline tickets from San Jose to Chicago by date

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  • February 2019
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  • August 2019
  • September 2019
  • October 2019
  • November 2019
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  • any
  • February 2019
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  • price
  • month of departure
  • month of return
$177
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$199
outward: Feb 23, 2019
7:25p SFO » 11:30p ORD
Alaska Airlines direct (4h05m)
inbound: Feb 28, 2019
12:40a ORD » 5:45a SFO
Alaska Airlines direct (5h05m)
$199
outward: Feb 23, 2019
7:25p SFO » 11:30p ORD
Alaska Airlines direct (4h05m)
inbound: Feb 28, 2019
12:40a ORD » 5:45a SFO
Alaska Airlines direct (5h05m)
$207
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 28, 2019
1:40a MDW » 6:25a SJC
Southwest Airlines direct (4h45m)
$212
outward: Feb 23, 2019
4:15p SFO » 9:40p MDW
Southwest Airlines 1 stop (5h25m)
inbound: Feb 27, 2019
1:01p ORD » 2:24a OAK
Spirit Airlines 1 stop (13h23m)
$221
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$222
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 27, 2019
4:45p ORD » 5:06a OAK
Spirit Airlines 1 stop (12h21m)
$237
outward: Feb 24, 2019
3:16a OAK » 1:33p ORD
Spirit Airlines 1 stop (10h17m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$250
outward: Feb 24, 2019
5:55a OAK » 9:39p ORD
Spirit Airlines 1 stop (15h44m)
inbound: Feb 27, 2019
4:45p ORD » 5:06a OAK
Spirit Airlines 1 stop (12h21m)
$256
outward: Feb 23, 2019
4:50p SJC » 4:38a ORD
Unknown Company 1 stop (11h48m)
inbound: Feb 27, 2019
5:41p ORD » 7:23p SJC
Unknown Company 1 stop (25h42m)
$262
outward: Feb 24, 2019
3:16a OAK » 1:33p ORD
Spirit Airlines 1 stop (10h17m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$263
outward: Feb 24, 2019
3:16a OAK » 1:33p ORD
Spirit Airlines 1 stop (10h17m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$273
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 27, 2019
1:01p ORD » 2:24a OAK
Spirit Airlines 1 stop (13h23m)
$280
outward: Feb 23, 2019
10:05p SJC » 3:50a MDW
Southwest Airlines 1 stop (5h45m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$286
outward: Feb 23, 2019
6:30p OAK » 2:34a ORD
Spirit Airlines 1 stop (8h04m)
inbound: Feb 27, 2019
10:59p ORD » 8:30a OAK
Spirit Airlines 1 stop (9h31m)
$316
outward: Apr 5, 2019
3:00p OAK » 7:42a ORD
Spirit Airlines 1 stop (16h42m)
inbound: Apr 7, 2019
11:00p ORD » 2:23a OAK
Spirit Airlines 1 stop (27h23m)
Return
Departure
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Airlines operating flights from San Jose to Chicago

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Travel tips for flights San Jose - Chicago

Average flight duration: 4h35m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Feb 16, 2019 11:48 PM, GMT-6
  • Weather:
  • min. 17ºF, max. 27ºF
  • Departure city:
  • San Jose, USA
  • Airport(s):
  • Norman Y. Mineta International Airport (SJC)
  • Reid-Hillview Airport of Santa Clara County (RHV)
  • Local time:
  • Feb 16, 2019 9:48 PM, GMT-8
  • Weather:
  • min. 38ºF, max. 52ºF