Cheap Flights from Boston to Chicago

Last Minute Deals

Last Minute Deals found within the last 12 hours
This Weekend
Next Weekend
See More

Top Vacation Deals

Browse Recent Deals found by other Expedia Users

Cheap BOS to Chicago flights

Book your BOS to MDW flights with Expedia and find last-minute Boston to Chicago airfare. Expedia offers discount airfare on multiple airline carriers that fly direct and indirect routes between BOS and MDW, with new flight deals and promotions almost daily. When you book your next trip from Logan Intl. to Midway Intl. with Expedia, you can rest assured you’re getting great ticket prices and excellent service from one of the world’s most trusted travel providers.

BOS to MDW Flight Schedule

A $ indicates that Expedia.com offers pricing for these airline's flights on the dates shown. A dot () indicates the airline has an available flight scheduled, but Expedia does not provide online booking at this time.

Popular Flights from Boston, Massachusetts

Browse popular flight destinations from Boston (BOS), and plan your next exciting trip. Expedia has cheap flights from Boston on multiple airline carriers, so book your next trip today!

Popular Flights from Chicago, Illinois

Browse popular flight destinations from Chicago (MDW), and plan your next exciting trip. Expedia has cheap flights from Chicago on multiple airline carriers, so book your next trip today!

BOS to MDW Route Map


Interesting Facts About Flights from Boston to Chicago (BOS to MDW)

  • AirTran Airways offers flights from Boston, MA to Chicago, IL.
  • The average aircraft occupancy on flights from Boston to Chicago in 2009 was 70.57%.
  • The average flight time from Boston, MA to Chicago, IL takes about 130 minutes.
  • The oldest aircraft servicing trips from Boston, MA to Chicago, IL in 2009 was Air Greenland's B737-4 from Boeing which started flying in 1990.
  • AirTran Airways offers the shortest flight times from Boston to Chicago.
  • The smallest aircraft servicing flights from BOS to MDW for Air Greenland is the B737-4 built by Boeing with 68 seats.
  • AirTran Airways operates the shortest flights from Boston to Chicago.
  • The shortest flight between BOS and MDW takes about 130 minutes.
  • AirTran Airways carried a total of 19,848 passengers from BOS to MDW in 2009.
  • The newest aircraft servicing BOS to MDW in 2009 was AirTran Airways' B717-2 from Boeing. The B717-2 started flying in 1999.
  • Air Greenland operated flights from BOS to MDW using one type of aircraft in 2009.
  • The shortest flight distance between Boston and Chicago is 861 miles.
  • There were 19,848 passengers that flew from Boston to Chicago in 2009.
  • Flight #882, operated by AirTran Airways, was the flight with the most delays in 2009, with 1 minute average delay between flights from Boston to Chicago.
  • 27,680 seats were available on flights from BOS to MDW in 2009. Of those seats, a total of 19,848 passengers flew on all flights from BOS to MDW that year.
  • In 2009, there was just one airline company serving flights from Boston to Chicago.
  • The largest aircraft servicing flights between Boston and Chicago from AirTran Airways is the B717-2 built by Boeing with 117 seats.

(Source: FAA & BTS 2009 Databases)