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 $200 / RT details

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Cheap Chicago airfares from $200/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/21/2023, 06:00 am from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 05:25 pm. The flight time is 11 hours and 25 minutes. The Returning flight departes on 04/05/2023, 05:00 am (other return dates are also available). Date posted: 01 Feb 2023

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

  • $200Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/21/202306:00 am
    Chicago, IL (ORD)Boston, MA (BOS)04/05/202305:00 am
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  • $234Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/25/202303:20 pm
    Chicago, IL (ORD)Boston, MA (BOS)03/06/202305:03 pm
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  • $251Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)04/25/202311:08 am
    Chicago, IL (ORD)Boston, MA (BOS)05/09/202310:00 pm
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  • $276Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)04/18/202311:08 am
    Chicago, IL (ORD)Boston, MA (BOS)05/03/202309:15 pm
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  • $304Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/13/202308:00 am
    Chicago, IL (ORD)Boston, MA (BOS)02/22/202310:00 am
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  • $61Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/09/202301:20 pm
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  • $67Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/13/202302:35 pm
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  • $141Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/19/202301:05 pm
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  • $365Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)02/13/202309:15 am
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  • $554Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/19/202307:00 am
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Know what to do when flying to Chicago?

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