I have no recollection of departing on any of the 13’s at MDW now that you mention it. I’ve taken off on 31C countless times in heading free with all the metal in the ground playing merry hell with the AHRS. Looking at the plates I don’t see an obvious reason why other than perhaps landing south is best accommodated by the circle east (think it’s a RNAV now too) for a 22 arrival.
The finest ass chewing of my career happened when the primary fuel truck’s brakes failed at Signature MDW. The backup had to be filled with fuel and then service 6 airplanes before us. We were trying to get to DPA to pick up passengers and take them to Columbus for an Ohio State football game. They refused to come to MDW, it was IFR, and the plane had almost no extra fuel onboard for a repo. So, we were really late when all was said and done. Luckily, I was flying with the guy who was usually the Flight Operations Duty Manager up at the puzzle palace. After getting my ass chewed by the owner/passenger who didn’t understand the issues at hand I sent my partner back to deal with him because it was going to end up on his desk anyway. I heard the ass chewing from the flight deck. My partner sat down, looked at me, and said “Yeah, that guys an asshat.” We turned in 15 minutes at MDW (aircraft limitation) and I saved 12 minutes of flight time by going low in the 30’s instead up climbing to the moronosphere. Didn’t matter to that guy. In the end he and his embarrassed by his actions family made the game. They just missed brunch with their son who attended OSU.
Two of the biggest aholes I had to deal with were at MDW. The third was in CLE. I don’t think that’s a coincidence, and I don’t miss it a bit.