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 $324 / RT details

Book your flight now with FlyFar and save!

Cheap Chicago airfares from $324/RT are provided by FlyFar. Outbound flight is leaving on 01/23/2017, 02:45 pm from San Jose (SJC) airport and arrives at Chicago Midway (MDW) at 08:50 pm. The flight time is 6 hours and 5 minutes. The Returning flight departes on 02/03/2017, 09:05 am (other return dates are also available). Date posted: 25 Dec 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

  • $324Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)01/23/201702:45 pm
    Chicago, IL (MDW)San Jose, CA (SJC)02/03/201709:05 am
    flyfar.ca check price
  • $325Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)01/23/201702:45 pm
    Chicago, IL (MDW)San Jose, CA (SJC)02/03/201709:05 am
    flightnetwork.com check price
  • $356Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)01/31/201709:15 am
    Chicago, IL (MDW)San Jose, CA (SJC)02/14/201706:30 am
    flyfar.ca check price
  • $357Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)01/31/201709:15 am
    Chicago, IL (MDW)San Jose, CA (SJC)02/14/201706:30 am
    flightnetwork.com check price
  • $384Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)02/15/201709:15 am
    Chicago, IL (MDW)San Jose, CA (SJC)03/01/201706:30 am
    flyfar.ca check price
  • $110United Airlines flight United Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)02/15/201706:41 am
    flighthub.com check price
  • $153Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)02/05/201706:30 am
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  • $155Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)02/15/201708:00 am
    flighthub.com check price
  • $159United Airlines flight United Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)01/24/201706:41 am
    flighthub.com check price
  • $161Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)01/29/201708:00 am
    flighthub.com check price
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