Chicago is a big city.. alright, one of the biggest. There is OF COURSE going to be danger with being in a large city like this. It doesn't matter where you are, although I would venture to say that Michigan Ave. is going to be one of the safest areas. Anyway, especially at night, avoid walking alone and down alleys and such. I don't think there's been a time after dark in Chicago when I haven't seen some shady looking character popping out from a corner. Heck, someone once started shining our shoes and got mad because we only gave him a couple bucks instead of like $30 or something ridiculous and started yelling at us. Then we ignored a man who opened his trenchcoat full of gold watches and necklaces, who proceded to yell at us. Yeah, anyway, just be careful at night.
And be careful of pickpockets... keep your wallet in your front pocket... I know they can still get it (they're really good), but it's at least slightly safer than having it in the back pocket. Maybe the absolute best idea is to get a 'wallet' that you strap around your neck and place under your shirt, keeping cash in there.
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