Midway - Chicago Municipal back then - was wayyyyy out in the country when it opened. Originally the airport terminal and hangars were in the southeast corner of today's airfield, near 63rd Street and Cicero Avenue.
The city tripled the size of the airfield in 1941 by acquiring an adjacent golf course and rerouting a railroad track. That led to the current square-mile airfield that still exists today.
There were houses on the east side of the airport all along. It wasn't until after WWII that the housing boom really engulfed the airport - most of the houses north, south and west of MDW
were built in the late 1940s and early 1950s, right as Midway was seeing its passenger traffic explode.
If you can believe it, the airport's "property line" at one point extended all the way to Harlem Avenue - almost five times the size of the current airport. The city sold it in the 1930s, saying they'd never need an airport that big. I wonder what would have happened if they'd kept that land and expanded Midway - ORD
might not have been necessary until the late 1960s.