It operated six Fokker F27 turboprop aircraft, and the call sign was "Wild Onion" in reference to the Chippewa Indian derivation of the name "Chicago."

Chicago Air had been working closely for two years with Saab Aircraft of Linköping, Sweden to acquire initially 10 Saab SF-340 turboprop commuter aircraft, which would have begun delivery in 1987 enabling expansion of services to Des Moines, Cedar Rapids, and Waterloo, Iowa; South Bend, Ft. Wayne, Lafayette, and Evansville, Indiana; and Kalamazoo and Grand Rapids, Michigan.

Chicago Air held a further option for 16 of the SF-340 aircraft, which would have enabled the carrier to expand services to additional markets in Michigan, Ohio, Missouri and Minnesota.

), a former senior manager at Continental Airlines; Booz Allen Hamilton; and New York Air.

Meehan and Christian together controlled 50 percent of the carrier's voting stock, with the remaining shares held mostly by a small group of Chicago area investors.