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Chicago (or Austin)

Any readers out there live in (or previously lived in) Chicago? Chicago is on the short list of where the wife and I might be heading after we leave in Augusta. We are looking to leave Augusta as soon as November (upon our return from India), depending primarily on a certain job hunt.

I’ve done some blogsearches on “moving to Chicago” or “moved to Chicago” (and even “Chicago noob“), but they haven’t turned up much in the way of helpful information.

Things I’d like to know include (but are not limited to):

  1. Where are the happening places to live?
  2. Given 1., which of these places are more affordable?
  3. Do you need a car or not?
  4. What’s the general political environment in Chicago? (Just curious)
  5. Is there much, if any, of a presence of web entrepreneurs in Chicago?
  6. How do Chicago-folks manage the bitterly cold winters? What do you do when you are compelled to stay inside?
  7. If you were a Chicago newbie when you got there, how’d you get to know folks?
  8. What are the central spots in Chicago? (This is similar to 1., I know)
  9. What’s the current economic feel in Chi-town? Is it full-on recession there yet?

Anything I’m not asking that should be asked?

Update 09/11/08:

The above questions — applied to Austin. Anyone live in Austin?

4 replies on “Chicago (or Austin)”

1. Where are the happening places to live? Depending how trendy you’re Lincoln Park, Lakeview, Old Town, Bucktown (more artsy)
2. Given 1., which of these places are more affordable? All pricey but Lakeview is reasonable.
3. Do you need a car or not? Nope, public transportation.
4. What?s the general political environment in Chicago? (Just curious) Democratic Machine baby… Obama walks on water
5. Is there much, if any, of a presence of web entrepreneurs in Chicago? Yes, you have people like 37signals, crowdspring, and other tech startups.
6. How do Chicago-folks manage the bitterly cold winters? What do you do when you are compelled to stay inside? Usually with a girlfriend and booze.
7. If you were a Chicago newbie when you got there, how?d you get to know folks? Not a newbie but I’m told we are very friendly compared to most cities… very Midwestern
8. What are the central spots in Chicago? (This is similar to 1., I know) Wrigley Field?
9. What?s the current economic feel in Chi-town? Is it full-on recession there yet? Not quite but it’s probably coming… good deals on real estate

Austin rocks too… it’s more diverse but Chicago has an entreprenuer hustle unlike any other city.

PS- cant believe I responded to this but I guess its what you do when your g/f makes you watch greys anatomy.

Yo. Chicago huh? I grew up there. You should target the North Side. Wrigleyville, Lincoln Park, Lakeview. All good areas. Every time I go back home I’m totally intrigued by the forest of townhouses/condos they built just South of Grant Park. Bet you might be able to find some good deals there too.

I would have to agree mostly with all that John has commented on. I am in real estate and have a pretty good handle on the hot areas of the city, and the best places to invest, etc. You’ll never lack for a fabulous dinner or cozy cheap dive bar. The winters can be long, so bring a nice coat and some hats, scarves, gloves, etc., Football is key too, especially this time of year, so hopefully you can find a love of the bears. Lastly, feel free to check out my blog, as my R.E. Partner and I talk endless about investment and new, fun stuff around our wonderful city. Good luck.

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