Cheap flights from Massachusetts to Chicago

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The name George Pullman certainly rings a bell.  He was famous for starting a luxury car.  He is also remembered for a neighborhood in Illinois and regarded as an industrialist in the area.  He was born as a New Yorker in 1831.  After 28 years, in the year 1859, Pullman transferred to Chicago and started building his dream there.  He was able to build the utopian worker community which resulted in one of the greatest disputes in Chicago making the ideal and perfect situation end.... (read more in our Chicago History)

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Boston 

Check our newest flight offers to Chicago:

  • $67Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)08/22/202405:48 am
    Chicago, IL (ORD)Boston, MA (BOS)09/04/202402:17 pm
    cheapoair.com check price
  • $87Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)08/22/202410:58 am
    Chicago, IL (MDW)Boston, MA (BOS)09/04/202402:17 pm
    cheapoair.com check price
  • $99Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)08/22/202405:48 am
    Chicago, IL (ORD)Boston, MA (BOS)09/04/202404:46 pm
    cheapoair.com check price
  • $113Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)08/22/202410:58 am
    Chicago, IL (MDW)Boston, MA (BOS)09/04/202404:46 pm
    cheapoair.com check price
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