My rules for exploring the less savory parts of Chicago

[strannik01]

Over the years, I visited many parts of Chicago that, quite frankly, most white people avoid. Some of those places are actually fairly safe - or, at least, no more dangerous than North Side lower-income neighborhoods that white people pass through all the time. Others actually are a bit more dicey. During the course of my visits, I developed a set of rules that helped me avoid getting into trouble... Most of the time. I am not sure how well they would work for other people, but they have worked for me, so I figured that I might as well share.

In no particular order.

1. Don't Be Afraid. If you are terrified of going to a certain place - don't. It will show. While it won't necessarily get you into trouble, it will make you nervous and more likely to make rash decisions. Now, that is not to say that you shouldn't listen to your instincts at all - they are there for a reason - but you shouldn't look for danger in every freaking driveway, either. 
2. Keep an Open Mind. A lot of people make the mistake of focusing on the damaged sidewalks, shuttered storefronts and graffiti. It's not that you should ignore them completely, but focusing on them will make it easier for you to miss the good parts. Washington Park look like a post-apocalyptic ruin, but the park that gives the neighborhood its name is one of the most beautiful in Chicago. Carbini-Green has beautiful murals and cool community gardens. Even in the worst, most desperately poor neighborhoods in Chicago, you can find signs of hope. 
3. Do Your Homework. Look up as much about the neighborhood as you can before you visit. Study its history. Memorize the layout of all the major and, if possible, minor streets. That way, you'll always know where you are heading (which does help). Look up community groups, local businesses and other noteworthy features. Looking up the location of the nearest police station wouldn't hurt, either. And speaking of which - do try to look up gang territory maps. The important thing to remember with those maps is that most of the violence occurs on the borders between two gang territories. Try to avoid them if possible.
4. Don't Be An Asshole. Smiling all the time and being painfully cheerful won't help you, but, at the same time, you'd be surprised just how far the small acts of kindness go. Do hold the door for a lady who's carrying groceries with both hands. If the people show interest in you, say "hi," ask them how they're doing. Generally, taking to people and taking genuine interest in what they have to say never hurts.
5. Having said that, Be Careful With Your Money. In a lot of those places, every other person will ask you to spare some change. And when it seems like you might be willing to spare some, they will ask for more. And more. And more. It can go on for a while. I don't fault the people for doing it -  they have to survive somehow  but you can't help everyone. So if you must give money, know when to stop. (On related note, don't carry too much money. This is where advance research helps. Before you go in, get an idea of how much money you absolutely need and how you plan to spend it. Also, don't bring credit/debit cards. Most stores won't take them, and they are just one more thing you have to worry about).
6. When In Rome, Do As Romans Do. Sort of goes along with "don't be an asshole." Do shop at local stores. Do grab some food at a local eatery. You don't have to, but it doesn't hurt. Besides, it supports local business in struggling communities. Speaking of which... During the summer, you see a lot of kids selling water bottles. They aren't usually that much cheaper than what you can get at a corner store, but in the more troubled neighborhoods, corner stores can take a while to find, and, hey - water is water.
7. Be Aware. Common sense, but just something to keep in mind. You don't want to get paranoid, but you don't want to be oblivious, either.
8. If Somebody Tells You to Run, Run. This has happened to me before several times. People told me not go to places, or to get the hell out. My policy is not to argue and do what they say. Because it's always better to be safe than sorry.

Well... That should about cover it.