I've lived in the city for 13 years and here are some tips:
- The only area we call "downtown" is the loop. When you say you want to be downtown but then talk about Lakeview, Lincoln Park, you will get a lot of confused looks. Most Chicagoans refer to parts of the city by their neighborhood.
- Parking is absolutely atrocious. If you value your A4 at all, factor in the cost of a garage. Lincoln Park and Lakeview especially, street parking is not the way to go. Streets are very narrow and your front and rear bumper will get destroyed. People park by feel and do not care whatsoever about their vehicles.
- Chicago has so many awesome neighborhoods, you have to figure out what is important to you to figure out where to live.
I would start by figuring out where you are going to work. If you are going to work "downtown" aka in the loop, you want to be close to the L trains to get to work. If you are going to work in the suburbs, close to the highway is a must.
- Which neighborhood to live in definitely is a personality test. If you like to hit the bars all the time, love football/college sports/baseball then Lakeview, Wrigleyville, Lincoln Park, or Wicker Park (close to division ave). If you are more of a hipster mentality, enjoying the dive bars and oddities, hang out at a brewery or coffee lover, then you want Wicker Park, Logan Square, West Town, Ukrainian Village. If you love to spend time at the beach or be outdoors in the park then you want Uptown, Andersonville, Edgewater, Rogers Park. If you have expensive tastes and the means for it, Old Town, Gold Coast, River North. If you're a foodie and have a dog, West Loop. I've lived in all those areas throughout my 13 years and now I live in Logan Square. The best part is, if you don't like your neighborhood or find yourself spending a lot of time in a different neighborhood, you can easily move!
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