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 $113 / RT details

Book your flight now with FlyFar and save!

Cheap Chicago airfares from $113/RT are provided by FlyFar. Outbound flight is leaving on 02/07/2017, 11:15 am from Boston Logan (BOS) airport and arrives at Chicago Midway (MDW) at 01:05 pm. The flight time is 1 hours and 50 minutes. The Returning flight departes on 02/22/2017, 09:45 pm (other return dates are also available). Date posted: 15 Sep 2016

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

  • $113Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)02/07/201711:15 am
    Chicago, IL (MDW)Boston, MA (BOS)02/22/201709:45 pm
    flyfar.ca check price
  • $114Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)02/07/201711:15 am
    Chicago, IL (MDW)Boston, MA (BOS)02/22/201709:45 pm
    flightnetwork.com check price
  • $123Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)10/06/201605:35 am
    Chicago, IL (MDW)Boston, MA (BOS)10/13/201609:55 pm
    flyfar.ca check price
  • $124Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)10/06/201605:35 am
    Chicago, IL (MDW)Boston, MA (BOS)10/13/201609:55 pm
    flightnetwork.com check price
  • $125Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/07/201707:00 am
    Chicago, IL (ORD)Boston, MA (BOS)02/22/201707:15 pm
    flighthub.com check price
  • $48Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)10/18/201601:16 pm
    cheapoair.com check price
  • $48Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)10/18/201601:16 pm
    flyfar.ca check price
  • $51Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)10/18/201601:16 pm
    flightnetwork.com check price
  • $52Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)10/18/201607:58 am
    flighthub.com check price
  • $53Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)10/18/201607:58 am
    cheapoair.com check price
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Know what to do when flying to Chicago?

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