Midway Airlines was formed by Jet Express, a commuter air carrier that operated code sharing feeder services for Trans World Airlines and USAir during the late 1980s and early 1990s. After an abortive attempt at New York-Chicago service, as well as Chicago-Denver and Chicago-Dallas, Midway moved to Morrisville, North Carolina, and set up a hub at Raleigh-Durham International Airport (RDU). Midway's arrival at RDU coincided with the closure of an American Airlines hub there.

At the height of its operations, Midway offered almost 200 flights daily from RDU to 25 destinations on the East Coast, and was used by many passengers travelling between the Northeast and Southeast.

Midway used a variety of aircraft while hubbed at RDU. Initially, the fleet consisted only of the Fokker 100. Midway added Airbus A320-200s to fly longer routes, but these routes eventually became unprofitable and the 320s were sold. Midway then obtained a large number of Bombardier CRJ-200s for expansion. By late 2000, the 100s became expensive to maintain and operate, so Midway replaced them with Boeing 737-700s. In November 2000, Midway expanded nonstop service from RDU to San Jose (SJC) and Los Angeles (LAX). Additionally, they started nonstop service to Denver (DEN) and seasonal service to Steamboat Springs via the Yampa Valley Airport (HDN), both in Colorado.

Two regional airline carriers known as Midway Connection provided service between RDU and smaller markets. First, Great Lakes Aviation using Beechcraft 1900 and Embraer 120 Brasilias in 1995 through 1997 and then Corporate Airlines, which used Jetstream 31 aircraft.

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