I spent several years as a retail store manager on Michigan Avenue. It always use to amaze me how I would see tourist walking into my store and being completely oblivious to the guy wearing the long, beat up overcoat in sunny 90 degree weather trailing close behind them. I would frequently walk around the seating area and notice women with their purses hanging open and with their wallets and personal items clearly visible. Chicago is a big city, but not necessary a dangerous one. Being safe is easy, but you just have to ensure that you keep a few things in mind:

1. Just Walking
If someone is curbside asking you for money, the chance is they actual want it! If you choose to give them cash, that's okay. However, don't pull out your purse or wallet on the street in order to dig out that cash or change. Have some in your pocket. Hand it to them, if you so desire, and keep moving.

2. Watching your stuff.
You're not in Kansas anymore (forgive me Kansas folks). If you're downtown shopping, even on the Magnificent Mile, you need to keep tabs of your purse, wallet, bags, laptop, etc. There were many occasions when I would see an unattended laptop on a table in the dinning area with no one around. I stood watching for a few moments just to hear the bathroom door swing open with someone jogging back to the table.

If you leave your stuff open and/or left alone, there is a good possibility that you might not have it by the end of the day. You don't have to grab you purse and bags if someone offers to open the door for you (now that would be weird), but just be aware of your things at all times. It sounds simple but it’s easy to forget while in the comfort of the high-end shopping world of Michigan Avenue.

3. Using buses and trains.
Know where you are going. Make sure of the route, particular if it's a bus. If you miss your stop a Wrigleyville to see a Cubs’ game, you can easily end up at a less desirable stop. Don't trail your family around in a bad neighborhood, stopping strangers to ask where's Harry Caray's restaurant You might find a helping hand or you might not.

4. No one here
If you're walking around the Loop (Chicago's Central Business District) during daylight hours, you'll notice quite a few people about their personal and professional business. However, on weekends and evenings, the Loop turns into a ghost town. State Street stays active for sometime while retailers remain open, but the rest is crickets. Remembering when the Loop may be deserted is worth remembering; particularly if you going somewhere at 8pm and its only "3 blocks" off State. You may want to consider a short cab ride instead of a light walk.

5. Looking around after sunset
The thieves come out "more" at night. You don't have to go back to your hotel room and get your piece at sunset. However, you do need to look around and become more aware of your surroundings. During the night hours in Chicago, you may have a good number of people around, but you'll probably see less of the friendly faces like your own.

6. Last key rule. Chicago is a fun city. If you are not comfortable, you won't think clearly and may not make the best decisions. If you're so focused on getting robbed or getting taken for a ride, you'll miss the reason why you came to Chi-town. Chicago is hardly one of the most dangerous cities in the country. We are not a mugging capital. However, don't have your fun ruined by not remembering the rules I've given you above. Stay safe and have fun.