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

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
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  • March 2019
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  • price
  • month of departure
  • month of return
$228
outward: Sep 16, 2018
10:18p OAK » 2:30a ORD
Spirit Airlines direct (4h12m)
inbound: Sep 19, 2018
2:50p ORD » 9:46p OAK
Spirit Airlines 1 stop (6h56m)
$301
outward: Sep 15, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 18, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
$301
outward: Sep 15, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 19, 2018
1:00p ORD » 7:18p SJC
Frontier Airlines 1 stop (6h18m)
$301
outward: Sep 16, 2018
8:09p SJC » 5:58a ORD
Frontier Airlines 1 stop (9h49m)
inbound: Sep 18, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
$301
outward: Sep 17, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 18, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
$301
outward: Sep 17, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 19, 2018
1:00p ORD » 7:18p SJC
Frontier Airlines 1 stop (6h18m)
$314
outward: Sep 15, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 20, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
$314
outward: Sep 16, 2018
8:09p SJC » 5:58a ORD
Frontier Airlines 1 stop (9h49m)
inbound: Sep 20, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
$314
outward: Sep 17, 2018
9:52p SJC » 5:58a ORD
Frontier Airlines 1 stop (8h06m)
inbound: Sep 20, 2018
1:00p ORD » 8:29p SJC
Frontier Airlines 1 stop (7h29m)
Return
Departure
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$300 $300 $314
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$300 $227 $314
17 September Sep Monday $outDate.dayShortName
$300 $300 $314
18 September Sep Tuesday $outDate.dayShortName
Choose when you'd like to depart to Chicago (USA):
Find the cheapest San Jose Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for San Jose - Chicago with these new dates, click on an offer. Want to depart from another city? Choose: Las Vegas - Chicago New York - Chicago London - Chicago Miami - Chicago San Francisco - Chicago See more routes

Airlines operating flights from San Jose to Chicago

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • all
  • Alaska Airlines
Alaska Airlines
outbound: Sep 16, 2018
Alaska Airlines 1 stop
return: Sep 19, 2018
Alaska Airlines 1 stop

Travel tips for flights San Jose - Chicago

Average flight duration: 4h12m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 20, 2018 8:22 PM, GMT-5
  • Weather:
  • min. 52ºF, max. 58ºF
  • Departure city:
  • San Jose, USA
  • Airport(s):
  • Norman Y. Mineta International Airport (SJC)
  • Reid-Hillview Airport of Santa Clara County (RHV)
  • Local time:
  • May 20, 2018 6:22 PM, GMT-7
  • Weather:
  • min. 54ºF, max. 70ºF