[1][2] It operated regional feeder services from Chicago Midway Airport under the name ATA Connection.

[3] Chicago Express became a wholly owned subsidiary of Amtran, later known as ATA Holdings, and now known as Global Aero Logistics, Inc.

For several months before its liquidation, the company also operated a hub in Indianapolis, part of ATA's failed plan for intrastate flights throughout Indiana.

Chicago Express Airlines relaunched June 1, 2021 as a International Cargo Charter Airline utilizing aircraft from International Cargo Carriers Operating Certificates and Aircraft At the time of ATA's grounding of Chicago Express on March 28, 2005, Chicago Express/ATA Connection had operated scheduled service to 17 destinations throughout the Midwest: Prior to the airline's dissolution, it announced new service from Indianapolis to Gary/Chicago International Airport in Gary, Indiana, however it never began service on this route.

At the time of termination on March 28, 2005, the Chicago Express fleet consisted of 16 Saab 340B configured to carry 34 passengers on short-haul and commuter flights.

One aircraft was written off during an engine run-up immediately prior to its resale to another operator when one propeller struck a ground power unit.