Cheap flights from San Diego to Chicago

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Travel tip: Don't miss to visit The Renaissance Society in Hyde Park.

Check our current prices for flights from San Diego 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 Diego to Chicago, you will need to run a search below.

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From $144 / RT details

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Cheap Chicago airfares from $144/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/06/2025, 08:07 pm from San Diego Lindberg (SAN) airport and arrives at Chicago O`hare (ORD) at 06:42 am. The flight time is 10 hours and 35 minutes. The Returning flight departes on 04/15/2025, 02:58 pm (other return dates are also available). Date posted: 19 Feb 2025

Price evolution for flights From San Diego To Chicago

Price overview for flights from San Diego to Chicago

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

  • $144Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (ORD)04/06/202508:07 pm
    Chicago, IL (ORD)San Diego, CA (SAN)04/15/202502:58 pm
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  • $148Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (ORD)04/06/202508:07 pm
    Chicago, IL (ORD)San Diego, CA (SAN)04/15/202506:45 am
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  • $154Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (MDW)04/06/202507:39 pm
    Chicago, IL (MDW)San Diego, CA (SAN)04/15/202506:45 am
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  • $155Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (MDW)04/06/202507:39 pm
    Chicago, IL (MDW)San Diego, CA (SAN)04/15/202502:58 pm
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  • $428Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (ORD)02/25/202503:28 pm
    Chicago, IL (ORD)San Diego, CA (SAN)03/11/202508:00 am
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  • $66Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (ORD)03/25/202506:25 am
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  • $68Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    San Diego, CA (SAN)Chicago, IL (ORD)03/25/202508:07 pm
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Know what to do when flying to Chicago?

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