Bus or train would be much cheaper, and probably faster 
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Isn’t the first airport more focused on receiving people, while the other one could be more geared towards handling packages, parking aircraft, and performing maintenance?
also take in mind, it may have come from another departure where ticket were sold for two destinations in order to fill easier and faster the aircraft
Or was it a reposition flight? Most of WN8501 flight history is long haul.
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All more likely than 165 people wanting to fly from the South Side to the Northwest Suburbs 
Of course in the sim I would take off RW31 and fly direct and put it down visual!
Yeah, IIRC 8xxx and 9xxx flight numbers are often assigned to repositioning flights, which makes for some odd pairings including very short flights like this. 
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Cities skyline solution; add a tram line to each airport or an underground metro linking all Chicago airports together
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IRL United, Air Canada, and Sun Country Airlines provide luxury bus connections between major hubs (Denver, Newark, and others) to nearby cities instead of using a regional jet.
Memories. Many years ago, as a mock business plan college assignment, my wife planned a company to run a blimp shuttle service between ORD and MDW. She got a pretty good grade on the plan, as I recall.
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Well, there is already an Orange Line Midway stop… if you take that to Clark/Lake, you can transfer to Blue Line, which takes you to O’Hare.