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 $174 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Chicago airfares from $174/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/11/2025, 07:54 pm from San Jose (SJC) airport and arrives at Chicago O`hare (ORD) at 06:36 am. The flight time is 10 hours and 42 minutes. The Returning flight departes on 03/25/2025, 08:00 am (other return dates are also available). Date posted: 21 Jan 2025

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

  • $174Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)03/11/202507:54 pm
    Chicago, IL (ORD)San Jose, CA (SJC)03/25/202508:00 am
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  • $200Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)02/02/202505:19 pm
    Chicago, IL (MDW)San Jose, CA (SJC)02/15/202501:32 pm
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  • $217Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)02/02/202503:35 pm
    Chicago, IL (ORD)San Jose, CA (SJC)02/15/202501:32 pm
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  • $458Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)02/02/202503:35 pm
    Chicago, IL (ORD)San Jose, CA (SJC)02/15/202508:44 pm
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  • $458Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (MDW)02/02/202505:19 pm
    Chicago, IL (MDW)San Jose, CA (SJC)02/15/202508:44 pm
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  • $80Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)03/01/202503:28 pm
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  • $90Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)03/12/202504:03 pm
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  • $143Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Jose, CA (SJC)Chicago, IL (ORD)03/12/202507:54 pm
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