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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$220
outward: Aug 20, 2018
9:45p SJC » 6:31a ORD
Frontier Airlines 1 stop (8h46m)
inbound: Aug 22, 2018
1:00p ORD » 7:25p SJC
Frontier Airlines 1 stop (6h25m)
$222
outward: Jul 27, 2018
3:00p OAK » 10:27p ORD
Spirit Airlines 1 stop (7h27m)
inbound: Jul 31, 2018
4:45p ORD » 9:21p OAK
Spirit Airlines direct (4h36m)
$234
outward: Sep 3, 2018
9:45p SJC » 6:28a MKE
Frontier Airlines 1 stop (8h43m)
inbound: Oct 31, 2018
11:01a MKE » 6:28p SJC
Frontier Airlines 1 stop (7h27m)
$258
outward: Oct 6, 2018
8:50a OAK » 1:04p ORD
Spirit Airlines direct (4h14m)
inbound: Oct 8, 2018
10:26p ORD » 5:29a OAK
Spirit Airlines 1 stop (7h03m)
$291
outward: Jul 23, 2018
5:15a OAK » 1:24p ORD
Spirit Airlines 1 stop (8h09m)
inbound: Jul 25, 2018
4:45p ORD » 9:21p OAK
Spirit Airlines direct (4h36m)
$336
outward: Jul 22, 2018
10:15p OAK » 2:23a ORD
Spirit Airlines direct (4h08m)
inbound: Jul 27, 2018
4:45p ORD » 9:21p OAK
Spirit Airlines direct (4h36m)
$437
outward: Nov 17, 2018
3:15p SJC » 11:48p ORD
Unknown Airline 1 stop (8h33m)
inbound: Nov 24, 2018
1:00p ORD » 9:08p SJC
Unknown Airline 1 stop (8h08m)
$706
outward: Sep 3, 2018
3:30p SJC » 1:58a MDW
Delta Air Lines 1 stop (10h28m)
inbound: Oct 31, 2018
11:14p ORD » 5:22a SJC
Delta Air Lines 1 stop (6h08m)
Return
Departure
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
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • all
  • Alaska Airlines
  • Frontier Airlines
  • United Airlines
United Airlines
outbound: Nov 17, 2018
United Airlines direct
return: Nov 24, 2018
Delta Air Lines 1 stop
Alaska Airlines
outbound: Nov 17, 2018
Alaska Airlines 1 stop
return: Nov 24, 2018
Alaska Airlines 1 stop
Frontier Airlines
outbound: Aug 1, 2018
Frontier Airlines 1 stop
return: Aug 7, 2018
Alaska Airlines direct

Travel tips for flights San Jose - Chicago

Average flight duration: 4h26m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 21, 2018 2:55 AM, GMT-5
  • Weather:
  • min. 67ºF, max. 75ºF
  • Departure city:
  • San Jose, USA
  • Airport(s):
  • Norman Y. Mineta International Airport (SJC)
  • Reid-Hillview Airport of Santa Clara County (RHV)
  • Local time:
  • Jul 21, 2018 12:55 AM, GMT-7
  • Weather:
  • min. 64ºF, max. 80ºF