Cicero/55th could be sunken below grade and the runway extended over it. The bigger problem is the RPZ, if you extended the runway you'd create hazards from the Orange Line viaduct and the freight tracks which are elevated. Plus the gains in length would be pretty modest.
If I had to expand Midway with godlike powers, I'd create a new north/south runway along Central from 55th down past 63rd and into the Clearing Yard as far as is feasible. A few blocks of houses would need to go, but comparatively little. You could possibly squeeze in an 8000' runway.
Either 63rd or 65th would have to go into an underpass beneath the new runway. Bundle this with a new overpass for Central over the Clearing Yards, which the Southwest Side has been requesting for decades to ease traffic on Cicero and Harlem.
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la forme d'une ville change plus vite, hélas! que le coeur d'un mortel...
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