Cheap flights from Chicago (CHI) to Boston (BOS)

Get away from The Windy City and explore a cultural mecca in New England, when you fly from Chicago to Boston. The city draws in both vacationers and those attending to business. Once you arrive at General Edward Lawrence Logan International Airport (BOS,) head to the nearby Seaport District and explore modern masterpieces at The Institute of Contemporary Art Boston. A great way to tour The Walking City is to stroll through the historic Boston Common Park, or to follow the marked paths of the Rose Fitzgerald Kennedy Greenway.

Key Facts

U.S. Route 1 runs through the heart of Boston and offers convenient access to neighboring communities like Quincy and Lynn. You can also navigate downtown Boston by driving on I-90. When using these highways, look for the exits towards Fenway Park and TD Garden, in order to reach Boston's premier sports venues. Head to Faneuil Hall and shop for some souvenirs in a marketplace that has been in business since colonial times. Take an elevator to the top of Prudential Tower to observe Boston's skyline from more than 700 feet above ground.

Hints and Tips

The flight from O'Hare International Airport (ORD) to General Edward Lawrence Logan International Airport takes two and a half hours. Once you get a rental vehicle at BOS, you'll be a short drive away from historic sites in the North End, like The Paul Revere House and other landmarks along the Freedom Trail.