Cheap flights from Massachusetts to Chicago

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Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals.... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Boston 

Check our newest flight offers to Chicago:

  • $107Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/01/201704:24 pm
    Chicago, IL (ORD)Boston, MA (BOS)02/07/201706:57 pm
    flighthub.com check price
  • $111Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/07/201710:55 am
    Chicago, IL (ORD)Boston, MA (BOS)03/22/201701:25 pm
    flighthub.com check price
  • $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
  • $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
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Recently found cheap flight deals

Multiple AirlinesChicago To Greenville Multiple Airlines airfares from Chicago in December
$428 Depart: 12/18/2016
Return: 12/30/2016

provided by FlyFar

United AirlinesBoston To Sao Paulo United Airlines airfares from Boston in November
$1564 Depart: 11/28/2016
Return: 12/05/2016

provided by Flightnetwork

Qatar AirwaysDallas To Johannesburg Qatar Airways airfares from Dallas in January
$862 Depart: 01/18/2017
Return: 01/24/2017

provided by Cheapoair.com

American AirlinesChicago To Mcallen American Airlines airfares from Chicago in December
$410 Depart: 12/21/2016
Return: 01/04/2017

provided by FareDepot

Multiple AirlinesSan Francisco To Dallas Multiple Airlines airfares from San Francisco in December
$788 Depart: 12/12/2016
Return: 12/19/2016

provided by Cheapoair.com

Lan AirlinesMiami To Brasilia Lan Airlines airfares from Miami in July
$1059 Depart: 07/26/2016
Return: 08/02/2016

provided by FlightHub

Jetblue AirwaysNew York City To Austin Jetblue Airways airfares from New York City in March
$370 Depart: 03/01/2017
Return: 03/31/2017

provided by FlightHub

Copa AirFort Lauderdale To Baton Rouge Copa Air airfares from Fort Lauderdale in December
$1830 Depart: 12/27/2016
Return: 01/05/2017

provided by Cheapoair.com

Alaska AirlinesHarrisburg To Atlanta Alaska Airlines airfares from Harrisburg in March
$2691 Depart: 03/22/2017
Return: 03/29/2017

provided by FlyFar

 

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