Used Cars for Sale in Chicago, IL

You should take the time to learn the grid system. Once learning the gird system, note that there are diagonal roads through the grid and sometimes they do weird things--particularly in the loop. Know that the loop is always insane as is the stretch of North Ave right by the Damen blue line stop (it's not as bad at the North/Clybourn red line stop). Same for the stretch on Belmont by the Belmont red line stop. Know how to do a proper U-turn--it will come in handy for snagging parking spots. Speaking of parking--get really good at parallel parking. You will hate everything ever if you don't. Did I mention the learning of the grid system. Because if you know that--at least for the main roads, even if your GPS is dead, it will be near impossible to get lost completely. And even then you could just stop and ask for directions. Just make sure you're in a friendly area. Speaking of friendly, if you don't want to give the beggars who roam the streets at stop lights money--roll up your window. It will make everyone's life easier--and less awkward. Back in Detroit, I wouldn't have doubted them for a second and they were always friendly and actually in need of help and willing to help you. Chicago is full of--pardon my French--assholes. At this point, if someone is asking for money for food I will go take them to buy food as opposed to giving them money. If they are being honest, they will appreciate a hot meal more anyways. I digress. Roll up your windows if you see one of the beggars and have no desire to give them anything. And whatever you do--don't make eye contact with them.

I haven't bought a car in this city, but I can say this from prior experience: shop around the used dealerships only because some people on Craigslist are going to screw you over. It's not as big of an issue for apartment, job, and random stuff hunting, but I have heard horror stores about cars. Now I bet you're wondering why I said used. New cars are nice. Not having your car stolen or vandalized because it's new is nicer. Additionally, from the research I've done about buying a car and getting it insured in Chicago, you want to make sure your car isn't going to be too old though because too new means high insurance as does to old. Hit that middle ground. Additionally, big cars are great. They can fit lots of stuff in them, road trips can involved more people and things, your dog can hang out in the back, etc.. HOWEVER, most parking spots are NOT going to accommodate you and your big car. Be prepared to be frustrated if you go for a larger car because parking will be a bitch almost always.

Anytime I get to drive in the city--I have a Zipcar account for a reason--I simply enjoy not having to take all my groceries from the store home via CTA. It can be a huge pain. Particularly when I lived in Edgewater at Ridge and Ardmore. To get to stores with good sales, it would literally be like an hour and a half public transit journey, minimum. It got to be extremely tiresome. That and it's always nice to know if a friend needs help moving stuff they can help pitch in for my Zipcar rental. It's easy, and I can drive them about. I can drive their stuff about. In general, I have no favorite memory. I enjoy whenever I do get to drive in the city because I get to so rarely as somehow I keep spending my savings on things and take a giant leap backwards from being able to purchase my own vehicle so I can go on random road trips. That will be the best thing about having my own vehicle and not having a zip car as that would make for a super expensive road trip. I love driving around the city and seeing things I'm not familiar with--but Chicago is severely lacking in stars. Though the nighttime skyline is a wonderful sight to behold.

Around Boystown. Boystown is a neighborhood not a road, so technically I have like three favorites in that neighborhood: Belmont, Clark, and Halsted. The traffic is always awful in the city, and Boystown provides me with wonderful things/people to look at or be like HEY! I've never been there. Mental note, check that out. There are so many nifty people and places in that area that I never find myself bored or irritated. Those are the main roads though. The small roads are kind of boring. All residential. Halsted is full of clubs and bars and restaurants and nifty stores. Same goes for Clark and Belmont. It's totally chaos on the weekend evenings/during pride. So be EXTRA cautious. Of course, normally being intoxicated I am not behind a wheel at that point and in the back of an Uber if I'm not on the sidewalk wandering. Seriously though, Chicago is the worst city to drive under the influence in. It's bad everywhere, but in Chicago it is fifty times worse due to population density. There are way more things and people to hit. Hell the one time I was involved in a drunk driving accident--I wasn't even driving! I was in a cab that was T-Boned where I was sitting, and I flew out of it and almost died. Don't be that guy who drunk drives home through Boystown. No body has time for that.

Some advice that I would give to other drivers driving around in this city of Chicago would be to watch all around you. Also, to take your time driving and do not let anyone rush you to get to your destination. If they are that impatient and are the passenger tell them they can walk, and if they are driving behind you and honking then they can always drive around. Do not let ANYONE force you to go faster because that could result in a bad crash. Believe me when I tell you this its better to go slower and get that safer than in a fast pace and get into a crash. You will mess up your car or maybe even your life. Also, always wear your seat belt. Does not matter if its "cool" or not. Your safety and if there are people in the car with you, their safety is important too. Always be on the look out for those crazy drivers because there are a lot of them out there and you need to try to literally steer away from them. That is the advice that I would give to other drivers driving in this city. Drivers are crazy so just be cautious and go at a pace that is most comfortable for you and wear your seatbelt.

Do not go through craigslist. People are so sketchy nowadays so I do not recommend going that route to get you a car. I would recommend a legit car dealership. Going to some random person on a random website is really dangerous and it is not a good idea. I do not know of a particular location because my car was a hammy down from my mom. A great hammy down by the way. If you do not want to go through a car dealership just yet and think that you can find something cheaper I recommend trying to see if a friend has a car he or she is trying to sell or a family member. Just make sure its someone you know that would not give you crap and rip you off. Also, you could go through car max, they have really great deals or even car rental places where they sell the car because they have to sell it after so many miles on it like enterprise for example. Also, make sure you figure out the car's history that is VERY important. It would definitely help you out when trying to figure out if you would want to buy the car or not.

MY favorite memory from driving in the city of Chicago is how there is always a detour to take if a street seems to blocked. What I mean, is that like when I first started working I would always seem to almost get into a fender bender with another car or a pole. I was a new driver at the time but my mom always told me that there is always multiple ways to get to your destination. Luckily, I have a gps, because my sense of direction is horrible. When I first started driving downtown Chicago, I remembered that and I always find this route to get to my work, I love driving close to navy pier, to see the ferris wheel even if it is just for a bit. I had finally found a good enough after like 2 months of driving back and forth to downtown Chicago for work. I am so glad that I found this route and I swear that I actually always have a place to park actually too which is rare but I've found my way around Chicago. When my coworkers ask me how I get there so fast, of course I don't tell them my secret route, because then they will use it and I will be back to a crowded and frustrating way to get to work and I would not want that to happen again.

201 East randolph street. This is my favorite road to drive by because there is always something beautiful to look at. Its always construction work yes but its not as horrible as where I would drive for work. Plus, if I am hungry there is always a place to eat or even shop which is amazing because I love to shop and eat. Even though I got into an accident once around that area and it took me awhile to come back around to that street again, like a month in a half, I did it with my mom driving and I missed it. SO, now I go over there and I just make sure that I am really careful with the way I drive anywhere not just on that street named above. It was definitely a learning experience for me but that is what made me love that area. It was very frustrating at first but the streets are way more wider so its definitely easier to maneuver around. You just have to worry about the high school students that would literally just get their license and like to speed. By the way that is how I got in to the accident but yeah, everything is a learning experience. However, that is definitely one of my favorite roads to drive on.