Cheap flights from Massachusetts to Chicago

Travel > North America > United States > Massachusetts to Chicago flights

Chicago is home to internationally recognized names in the entertainment scene: the Chicago Symphony, Lyric Opera, and Steppenwolf Theatre, Gutsy Steppenwolf Theater regularly showcase the talents of remarkable local actors. The Grammy-laden Chicago Symphony Orchestra is appreciated both at home and abroad and the Lyric Opera's lavish productions boast world-class singers and conductors. And let’s not forget film criticism, TV talk (who doesn't know Oprah!) and Second City... (read more in our Chicago Travel Guide)

Check current prices for flights to Chicago at our partners' sites:

Search and Compare cheap Flights

Enter your travel details:Step 1









Select merchants to compare:Step 2
TripversFlightnetworkExpediaBookingbuddyDealBaseTravelgroveTravelocity
 

Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)
From
FebMarAprMayJunJulAugSepOctNovDecJan
$208$111$170$198check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
more
Boston 

Check our newest flight offers to Chicago:

  • $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
  • $170Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)04/26/201704:55 pm
    Chicago, IL (ORD)Boston, MA (BOS)05/09/201701:26 pm
    flighthub.com check price
  • $172Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/01/201704:54 pm
    Chicago, IL (ORD)Boston, MA (BOS)03/06/201709:35 am
    flighthub.com check price
  • $174Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/01/201710:57 am
    Chicago, IL (ORD)Boston, MA (BOS)03/06/201709:35 am
    cheapoair.com check price
  • $180Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/01/201707:30 am
    Chicago, IL (ORD)Boston, MA (BOS)03/06/201708:11 am
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesDetroit To Santiago Multiple Airlines airfares from Detroit in April
$1553 Depart: 04/19/2017
Return: 05/02/2017

provided by Travelgrove

Multiple AirlinesAnaheim To Chicago Multiple Airlines airfares from Anaheim in February
$1131 Depart: 02/24/2017
Return: 03/03/2017

provided by FlyFar

Alaska AirlinesWichita To San Diego Alaska Airlines airfares from Wichita in June
$698 Depart: 06/14/2017
Return: 06/21/2017

provided by FlyFar

Southwest AirlinesSan Francisco To Boise Southwest Airlines airfares from San Francisco in March
$325 Depart: 03/15/2017
Return: 03/22/2017

provided by Flightnetwork

Multiple AirlinesNew York City To Budapest Multiple Airlines airfares from New York City in July
$903 Depart: 07/11/2017
Return: 09/12/2017

provided by Travelgrove

United AirlinesCharlotte To Grand Cayman United Airlines airfares from Charlotte in February
$792 Depart: 02/25/2017
Return: 03/04/2017

provided by FlyFar

Multiple AirlinesMedford To Nashville Multiple Airlines airfares from Medford in May
$599 Depart: 05/09/2017
Return: 05/17/2017

provided by Travelgrove

Virgin AmericaMaui To Orlando Virgin America airfares from Maui in March
$1156 Depart: 03/21/2017
Return: 03/28/2017

provided by FlightHub

American AirlinesToronto To Minneapolis American Airlines airfares from Toronto in May
$473 Depart: 05/17/2017
Return: 05/23/2017

provided by Travelgrove

 

Specify your search details. Browse the cheapest flights from Massachusetts to Chicago, Chicago hotel rooms and Massachusetts to Chicago vacation packages from the most popular providers, airline consolidators and travel search engines.

Chicago Pictures
  • Bean - Chicagoview
  • City Reflections - Chicagoview
  • cool site - Chicagoview
  • Chicago Limousine Bus - Chicagoview

more Chicago travel deals

   Welcome to Travelgrove  register tell a friend bookmark it 
 
This airfare deal was found   ago. Click "Check price" to see current prices!
*