Cheap flights from San Jose to Chicago

Travel > North America > United States > San Jose to Chicago flights

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Check our current prices for flights from San Jose to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from San Jose to Chicago, you will need to run a search below.

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From $286 / RT details

Book your flight now with FlyFar and save!

Cheap Chicago airfares from $286/RT are provided by FlyFar. Outbound flight is leaving on 10/20/2016, 08:40 am from San Jose (SJC) airport and arrives at Chicago Midway (MDW) at 02:50 pm. The flight time is 6 hours and 10 minutes. The Returning flight departes on 10/23/2016, 07:00 am (other return dates are also available). Date posted: 10 May 2016

Price evolution for flights From San Jose To Chicago

Price overview for flights from San Jose to Chicago

Recent Deals on Flights from San Jose to Chicago:Roundtrip / Oneway

  • $286Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)10/20/201608:40 am
    Chicago, IL (MDW)San Jose, CA (SJC)10/23/201607:00 am
    flyfar.ca check price
  • $287Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)10/20/201608:40 am
    Chicago, IL (MDW)San Jose, CA (SJC)10/23/201607:00 am
    flightnetwork.com check price
  • $311Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)09/15/201608:40 am
    Chicago, IL (MDW)San Jose, CA (SJC)09/19/201607:50 pm
    flyfar.ca check price
  • $312Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)09/15/201608:40 am
    Chicago, IL (MDW)San Jose, CA (SJC)09/19/201607:50 pm
    flightnetwork.com check price
  • $316United Airlines flight United Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/10/201605:55 pm
    Chicago, IL (ORD)San Jose, CA (SJC)06/17/201605:45 am
    faredepot.com check price
  • $119United Airlines flight United Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/09/201605:55 pm
    flighthub.com check price
  • $146Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/21/201612:55 pm
    flighthub.com check price
  • $147Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/27/201607:45 am
    flighthub.com check price
  • $147Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/09/201612:55 pm
    flighthub.com check price
  • $162Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)06/21/201609:40 am
    faredepot.com check price
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