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Began operations in May 1986 as a regional airline connecting Chicago Midway International Airport with destinations in Wisconsin, Michigan, and Illinois. The airline served Madison, Green Bay, La Crosse, Eau Claire, Wausau, Traverse City, Peoria, Springfield, and the Quad Cities. Operated six Fokker F27 turboprops subleased from Midstate Airlines and used the callsign "Wild Onion," referencing the Chippewa origin of the name "Chicago." Midstate Airlines also provided maintenance services for the fleet at Central Wisconsin Airport.
The airline planned significant expansion with an agreement to acquire 10 Saab SF-340 turboprop aircraft in 1987, with options for 16 more. The airline offered complimentary meal service, premium beverages, and enhanced in-flight amenities, targeting regional passengers seeking quality service at competitive fares.
Intensified competition, including widespread discount non-refundable fares and aggressive marketing from rival airlines, led to Chicago Air’s financial struggles. The airline merged into Midstate Airlines on October 14, 1986, and entirely ceased operations in November 1986 when Midstate ended the sublease for the Fokker F27s.
