Cheap flights from Boston to Chicago

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Travel tip: Visit Chicago on your holidays!

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

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From $126 / RT details

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Cheap Chicago airfares from $126/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/30/2024, 01:53 pm from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 10:12 pm. The flight time is 8 hours and 19 minutes. The Returning flight departes on 06/07/2024, 09:20 pm (other return dates are also available). Date posted: 15 Apr 2024

Price evolution for flights From Boston To Chicago

Price overview for flights from Boston to Chicago

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway

  • $126Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/30/202401:53 pm
    Chicago, IL (ORD)Boston, MA (BOS)06/07/202409:20 pm
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  • $157Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)05/30/202412:32 pm
    Chicago, IL (MDW)Boston, MA (BOS)06/07/202409:20 pm
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  • $176Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)05/30/202412:32 pm
    Chicago, IL (MDW)Boston, MA (BOS)06/07/202405:58 pm
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  • $277Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/09/202406:10 am
    Chicago, IL (ORD)Boston, MA (BOS)05/18/202410:40 am
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  • $84Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)04/27/202412:41 pm
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  • $84Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)04/27/202405:05 am
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  • $84Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)05/12/202409:08 am
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  • $90Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/12/202409:08 am
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  • $93Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/12/202409:32 pm
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Know what to do when flying to Chicago?

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