Chicago is a big city, and in any big city there are criminals waiting to take advantage of an unsuspecting tourist. While I'm giving you common-sense guidelines to make sure you're not victimized, please don't think Chicago is a city full of crime because it's not. In fact, most of the sneaky thefts I've heard about took place at least 5 years ago! Things are safer now! Keep your bags close to you. Guys, wear a money belt or keep your wallet in your front pocket. Women, put your purse strap over one shoulder and have the bag resting on the opposite hip. If your purse can easily be plucked off your shoulder, it just might be! Never put your purse on the back of your chair at a restaurant. Also...if you end up eating at a sidewalk cafe, don't set your purse on the ground unless you put your leg through the strap--otherwise, a thief may grab it and run. Wherever you go, just assume that there could be someone watching you, waiting for you to leave your stuff unattended so they can steal it.
One popular scheme that someone tries to pull on me every year is the old, 'I locked my keys in my car...would you loan me $40 to pay the locksmith--then I'll get my money out of the car and pay you back.' Of course, the car is always way down the street (conveniently out of view). In fact, there IS no car...no locksmith on the way...and you will never see that money again if you are trusting enough to give it away. My sister had the same guy tell her the exact same story two days in a row in our neighborhood. Fortunately, she didn't fall for it either time. Usually, any hard luck story is a con--unless someone is homeless, of course.
Unfortunately, there ARE a lot of homeless people in the city. A large population of them actually LIVE back in the cave-like construction of Lower Wacker Drive (an underground street designed to help people avoid traffic congestion downtown). I get approached by about 3 homeless people everyday on my trip downtown. Some of them are selling a newspaper called 'Streetwise,' which costs $1 and allows them to make a living with a little dignity. It's pretty sad, though. Just so you know, some of them might try to hand you a 'Streetwise' and you might take it, assuming it's free. Then they'll demand payment from you. If you don't want to buy one, it's best to just say, 'No, thank you.'
One more important warning if you drive into the city or rent a car once you're here: Make sure you thoroughly investigate your parking spot if you park on the street. Many neighborhoods are zoned residential, which means you can't park on their streets unless you live in the area and have a special sticker on your car. Metered spots are a rare find and you have to make sure you put in enough money to cover the length of time you're parked. They monitor parking meters regularly and will give you a ticket the second your time runs out! If you're renting a car, the city will make the company pay. Of course, the company will make you pay. If you have your own car, you can decide if you want to take your chances by 'forgetting' to pay the ticket. After 5 tickets, the police can put a 'boot' on your tire, rendering your car immovable. They won't take it off until you pay. If you park on the street overnight, make sure you check every sign on the street (not just around your car). If there's a sign anywhere on the street that indicates they tow after 2am or from October-April or between 7-9am, you WILL be towed! It's very expensive to get your car back--not to mention tedious and horribly bureaucratic. They make a lot of money on this, and it's quite a business for them, I'm sure. Be careful!!
But please don't let these warnings scare you too much. If you're careful, you'll be okay. These things are just a few small annoyances in a great big city!
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