Following the Airline Deregulation Act of 1978, Midway first emerged as a discount carrier. It was noted for its low fares and ease of connections at Midway Airport. The airline purchased three DC-9s from TWA and began flying to Cleveland (Lakefront), Kansas City, and Detroit. The scheduled service was an instant success. In 1980 Midway bought five more DC-9s and added flights to St Louis, New York La Guardia and Washington National; they also shifted to CLE, and tried MSP and quickly dropped it. has several Midway route maps from 1980 to 1989.
During the 1980s the airline adopted a combination of all-leather two-by-two seating to business markets and all-coach seating to vacation destinations. This idea was eventually dropped due to the impact on revenue caused by eliminating seats, and the confusion it created in the minds of connecting passengers.
The carrier expanded into the Caribbean via the purchase in 1984 of the assets of Air Florida, which had gone into bankruptcy. It proved to be good mix of business and vacation travel revenue. Midway flourished under the leadership of David R. Hinson (CEO 1985 to 1991), but a second hub at Philadelphia International in 1990 proved unsuccessful.
In 1986 the company assisted in setting up a successful regional affiliate, Midway Connection, as a feeder from small communities in Illinois, Indiana, Wisconsin, and Michigan. This carrier was established following the bankruptcy of Chicago Air, a regional carrier which attempted a similar, but independent feeder operation in 1986.
On a June 1988 weekday Midway scheduled 116 nonstop flights into MDW from 25 airports, along with 75 Midway Connection nonstops from 17 other airports. They flew MDW-MIA-STX-STT and back and MDW-FLL-NAS and back; aside from those all Midway flights were nonstop to/from MDW.
Midway was noted for friendly employees and attentive service, and its Chicago South Side passengers were fiercely loyal to their hometown airline. Some of the signature inflight service items were after-dinner chocolate wafer mints and hot hand towels to the entire cabin, both of which had originally caught on with Midway's business clientele.
The airline purchased the hub operation of Eastern Air Lines at Philadelphia International Airport in 1990. However, this expansion, in direct competition with the Philadelphia hub of US Airways, coupled with the run-up of airline fuel prices during the Persian Gulf War in 1991, strained the company's financial resources. The airline filed Chapter 11 and attempted to reach agreement with Northwest Airlines for a sale. The sale was nearing completion when Northwest suddenly pulled out of the deal November 12, 1991. Midway ceased operations November 13, 1991 and filed under Chapter 7 bankruptcy laws. Settlement was completed in summer, 2005.