Illinois brokers have been placing risks at Lloyd's since at least the late 1800s. The first regulation of Lloyd's in Illinois was the Lloyd's Act of 1911. Lloyd's commenced business as licensed insurers in Illinois in 1929, and in 1931, Lloyd's appointed John S. Lord as attorney in fact in Illinois.

The Lloyd's Illinois attorney in fact remained with the law firm of Lord, Bissell & Brook LLP until 2004, when Lloyd's Illinois, Inc. was formed to be the Lloyd's general representative in Illinois.

During its long history in Illinois, Lloyd's has been at the forefront of insurance innovations, from providing coverage for early steam automobiles to excess fire, reinsurance, umbrella liability, and professional liability.