Cold-copping WEED? And on the West Side of Chicago none-the-less? (This would be a different story if you were cold-copping in Europe or more lenient jurisdictions, but the West Side is not one of those places). Are you serious? In this day and age, there is absolutely NO reason to be doing that. I'm sure you could find at least 3 reputable, non-sketchy, dealers (who lack the affiliation of some violent gang) just by making a few friends and talking to people. Expand your social circle and you will find plenty of weed in no time.
It's just so not worth it. If you're going to do that you should always be on foot. Park your car within walking distance of your spot, or take the bus. Getting caught in your car means they impound your car and it costs something like $1,000 to get it out. Second time they catch you in that area again (I'm not 100% sure what the laws are, but I know they can take the car if they find you in possession or with paraphernalia, BUT they might also be able to take the car with just "reasonable cause" because they found inconsistencies with your story or were pissed that they knew you were down there to cop, but couldn't find anything on you) the impound fee INCREASED, and there may be additional penalties, I'm not sure. You know what they do the third time they catch you? They take your fucking car. And you can't pay to get it back. They just straight-up repossess your vehicle and then sell it at police auction. If you're a lawyer driving around in an $80,000 Lexus, that might seem pretty ridiculous to lose that car just for 3 times getting caught with paraphernalia. But to someone driving around in a $1.500 15=year old piece of junk, maybe the LOSING YOUR CAR FOREVER part isn't as big of a deterrent to them.
ALSO, YOU'RE A LAWYER. Possession/paraphernalia charges could really hurt your career. Not worth risking it for the "adrenaline rush" of copping weed in a sketchy situation; a situation in which, statistically speaking, over enough trips over a long enough time period, 99% eventually get caught in some way.
If in the future the day comes that you need access to harder drugs, maybe you won't know where to pickup from any legitimate friend-of-a-friend source, and in that scenario, you end up having to cold-cop on the streets. But if you're only buying weed, the most easily accessible narcotic in the world, you should be doing it in a way that is of the least risk to you. There's just no sense in gambling over something so stupid.