Cheap Flights from Boston to Chicago — $94

Primary airport serving Boston and the New England region, offering domestic and international flights with multiple terminals and direct public transit, ferry, and road connections to downtown.

Near Portsmouth, New Hampshire; a joint military–civil airfield serving military operations and civilian flights, convenient for travel to the Seacoast region and southern New Hampshire.

Former single-runway general aviation facility on Chicago’s lakefront adjacent to downtown, serving business and private flights until its abrupt closure in 2003.

General aviation reliever near Chicago in West Chicago, Illinois, serving corporate, private and flight-training traffic with hangars, FBO services and maintenance, convenient for access to the western suburbs.

Serving Chicago’s Southwest Side and downtown, it handles mainly domestic flights with a strong presence of low-cost carriers and easy connections via the 'L' Orange Line and nearby expressways.

Major air hub serving Chicago and the Midwest, with extensive domestic and international routes, multiple terminals, and direct transit links to downtown for convenient connections.

General aviation reliever airport northwest of downtown Chicago, serving business, private and charter flights and offering flight training and FBO services for the northern suburbs.

Serving Rockford and northern Illinois, the airport handles domestic passenger flights and is a major cargo hub. Convenient ground links provide access to the Chicago metro and surrounding communities.