• Fast. Easy. Affordable.


In 1956, Richard H. Mason entered the insurance field and saw the growing demand in the non-standard automobile insurance market. City Squire Agency was originally located in the vicinity of 63rd Street and Western Avenue on Chicago’s southwest side. In 1982 our name became Mason Insurance Group, combining City Squire Agency, Duncan Insurance Agency, Mason Insurance Agency and FirstPay, Inc., our premium finance company. For 21 years we were located at the corner of 80th Street and Kedzie Avenue. In 1999, we moved to our more spacious location on 95th Street in Oak Lawn.

Our home office is currently located at 4939 W. 95th Street in Oak Lawn, where our friendly professional staff of 14 are eager to solve your insurance challenges. Also, we have another location in Chicago at 3257 N Sheffield Avenue, Suite 119.