Midway International Airport, Chicago’s second airport on the city’s southwest side, is playing catchup.

In February, the city approved the final parts of a multiyear, $248 million modernization plan to expand the airport as well as its retail options, security operations and parking facilities.

The move to make the city-owned airport a more inviting experience for the millions of people who pass through it every year is a priority that Chicago officials, like other airport operators throughout…