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Now was the air just let out of your tires, or have you had to patch or replace tubes/tires and such? I know alot of Pilsen has come under some serious gentrification in recent years and from what I know alot of residents are pissed about it(hence the signs perhaps?), but idk about attcks on peoples bikes. I would talk to your roommate and figure out a way to place both your bikes within the fence as locking to a street sign since the bike can either be lifted over, or the sign removed from the ground isnt a sound place to lock your bike and opens yourself up to theft.
Bikes as a sign of yuppiness? Idk how nice your ride is, but isnt it usually the other way around, yuppies(as it were)calling people on bikes hippies, or hippies who cant afford cars? I know they run a CM down there in Pilsen now. I havent been out to it yet, so idk how big it is, but maybe some of the residents are upset about it? I dont see that really happening in my experiences with pilsen, but i wouldnt excluse it from the possabilities, I havent spent time down there in quite some time.
Critical Mass to answer your question.. Or in this case, Pilsen/Little Village Circular Mass
http://www.bikechicago.info/PCM/PLVCM.html
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