Cheap flights from Massachusetts to Chicago

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

The Great Chicago Fire was considered one of the most tragic points in the history of Chicago.  The fact that firefighters were sent to a wrong neighborhood lead the fire to crumble up the walls of wooden houses and other properties found near the area.  It even reached the north and the east of DeKoven Street leaving a lot of infrastructures to ashes.  This left the city embarked to a rebuilding program replacing wooden buildings with stone.  They even created the first modern fire... (read more in our Chicago History)

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
Travelgrove
 

Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)
From
JunJulAugSepOctNovDecJanFebMarAprMay
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
check
fares
more
Boston 
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesNew York City To Kingston Multiple Airlines airfares from New York City in April
$515 Depart: 04/04/2025
Return: 04/09/2025

provided by Cheapoair.com

Multiple AirlinesCleveland To San Jose, CA Multiple Airlines airfares from Cleveland in March
$240 Depart: 03/13/2025
Return: 03/18/2025

provided by Cheapoair.com

Spirit AirlinesNew Orleans To New York City Spirit Airlines airfares from New Orleans in April
$116 Depart: 04/13/2025
Return: 04/22/2025

provided by Cheapoair.com

LufthansaSan Francisco To Tel Aviv Lufthansa airfares from San Francisco in April
$1116 Depart: 04/02/2025
Return: 04/08/2025

provided by Cheapoair.com

Multiple AirlinesSan Jose To Phoenix Multiple Airlines airfares from San Jose in September
$131 Depart: 09/08/2024
Return: 09/20/2024

provided by Cheapoair.com

WestjetWinnipeg To Minneapolis Westjet airfares from Winnipeg in April
$344 Depart: 04/01/2025
Return: 04/08/2025

provided by Cheapoair.com

United AirlinesCedar Rapids To Brownsville United Airlines airfares from Cedar Rapids in August
$382 Depart: 08/09/2019
Return: 08/18/2019

provided by FlyFar

WestjetToronto To Acapulco Westjet airfares from Toronto in June
$797 Depart: 06/03/2025
Return: 06/11/2025

provided by Cheapoair.com

Multiple AirlinesBoston To Mumbai Multiple Airlines airfares from Boston in April
$831 Depart: 04/02/2025
Return: 04/09/2025

provided by Cheapoair.com

 

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!
*