Cheap flights from Massachusetts to Chicago

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

Though residents complain about the cold weather that lasts almost through the whole year, at least on a winter day, they can duck into such popular clubs as Andy's, where there's hot jazz even at noon. The best time to visit is between May and October when the weather is the most predictable. Then you could head out to ivy-covered Wrigley Field to catch baseball's Cubs in action, or take a cruise boat under the bridges of the Chicago River at sunset.... (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
TripversFlightnetworkExpediaBookingbuddyTravelgroveTravelocity
 

Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)
From
JanFebMarAprMayJunJulAugSepOctNovDec
$118$119$136check
fares
$214check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
more
Boston 

Check our newest flight offers to Chicago:

  • $118Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/24/201805:03 pm
    Chicago, IL (ORD)Boston, MA (BOS)01/29/201807:42 pm
    travelgrove.com check price
  • $118Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/24/201807:01 am
    Chicago, IL (ORD)Boston, MA (BOS)01/29/201807:42 pm
    cheapoair.com check price
  • $119Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/09/201807:01 am
    Chicago, IL (ORD)Boston, MA (BOS)02/20/201809:40 am
    cheapoair.com check price
  • $119Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/01/201807:01 am
    Chicago, IL (ORD)Boston, MA (BOS)02/12/201807:42 pm
    cheapoair.com check price
  • $119Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/29/201805:03 pm
    Chicago, IL (ORD)Boston, MA (BOS)02/06/201807:42 pm
    travelgrove.com check price
cheap domestic and international flights

Recently found cheap flight deals

Jetblue AirwaysHartford To Orlando Jetblue Airways airfares from Hartford in April
$781 Depart: 04/13/2018
Return: 04/22/2018

provided by Travelgrove

LufthansaPhoenix To Edinburgh Lufthansa airfares from Phoenix in January
$1340 Depart: 01/16/2018
Return: 01/26/2018

provided by FlightHub

Alaska AirlinesToronto To Anchorage Alaska Airlines airfares from Toronto in January
$625 Depart: 01/23/2018
Return: 02/06/2018

provided by FlightHub

United AirlinesTampa To Toronto United Airlines airfares from Tampa in April
$506 Depart: 04/04/2018
Return: 04/13/2018

provided by Travelgrove

Multiple AirlinesDallas To Perth Multiple Airlines airfares from Dallas in October
$1562 Depart: 10/25/2017
Return: 11/08/2017

provided by Flightnetwork

Multiple AirlinesNew York City To Honolulu Multiple Airlines airfares from New York City in May
$864 Depart: 05/08/2018
Return: 05/22/2018

provided by Travelgrove

LufthansaBoise To Manchester Lufthansa airfares from Boise in February
$1302 Depart: 02/14/2018
Return: 03/06/2018

provided by Cheapoair.com

Alaska AirlinesCalgary To San Diego Alaska Airlines airfares from Calgary in February
$581 Depart: 02/18/2018
Return: 03/03/2018

provided by Travelgrove

United AirlinesHouston To Vancouver United Airlines airfares from Houston in January
$659 Depart: 01/25/2018
Return: 02/08/2018

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