Midway (then called Chicago Municipal) was on the edge of the city when it opened in the 1920s. There were some neighborhoods to the immediate east (in the Garfield Ridge area) that were just starting to develop... the grid pattern of streets had been built, but construction of homes was sporadic.
If you look at aerials from that era, today's grid network of streets exists around the airport, but homes/businesses are few and far between. There are a few businesses on Cicero Avenue and 63rd Street, but still mostly empty lots. Then the Depression came and homebuilding came to almost a complete stop.
After World War II
the area around MDW
exploded... most of the houses that now hem in the airport were literally built in five years between 1945 and 1950. Remember, the streets and utilities were already hooked up, so it was easy to throw up an angular, then-futuristic 1950s Chicago bungalow. By 1950 the airport was completely surrounded by mostly new homes and businesses.