My kind of town?
August 7, 2008 7:07 PM   Subscribe

I want to know if it'd be a good idea for me to move to Chicago. I'm going to be spending a day or two there this weekend. I know there are plenty of AskMe questions by tourists wanting to know how to enjoy their brief stay there. My question is different: where should I go / what should I do to help myself decide if a more-or-less permanent move to Chicago would be a good idea for me?

Backstory: For a while I've been looking forward to ending up with a permanent job in NYC (I work in upstate NY right now). But lately I've been realizing that Chicago might be a better choice for me (lower cost of living; fewer of the NYC annoyances but still a big, exciting city; I have family nearby in Wisconsin, etc.).

The problem is that I have almost no experience actually being there, so my thoughts on whether it'd be a good idea to move there are frustratingly vague. While I know that a day or two probably isn't enough time to completely solve this problem, I want to do what I can in that time period.

I like a lot of your standard touristy stuff like museums, sightseeing, and concerts -- but I mention this to say that it's not what my question is about. I assume there's tons of great touristy stuff that I could find out about from guidebooks, etc. I'm much more interested in simply observing what everyday life is like.

More info:

- If I were to make this decision, it wouldn't be for at least a couple years (because of my current job).

- We'll be getting around by car this weekend, though I wouldn't have a car if I moved there.

- I tend to prefer funky/artsy/idiosyncratic neighborhoods to upscale ones. Of course, I'm not yet at the point of settling on a neighborhood since I don't even know if I'll move to Chicago -- but I am interested in checking out interesting neighborhoods to give myself a more vivid sense of what life would be like there.

- Since I'm primarily thinking of this as a choice between Chicago and NYC, I'd be especially interested to hear from people who have lived in both cities.

- I've been to Chicago a few times, but that was a while ago, mostly when I was too young to really absorb it.

Additional background info that might or might not be relevant: I'm a single straight white guy in my 20s. Vegetarian. Recently graduated from law school. I don't have family or close friends in Chicago. I have no interest in anything sports-related.
posted by jejune to Travel & Transportation around Chicago, IL (17 answers total) 13 users marked this as a favorite
Chicago is an amazing town. When I moved here about five years ago, someone told me, "Some people hate LA. Some people hate New York. But everyone loves Chicago." And it's been true so far. The city is quintessentially American and as such offers the best and worst of who 'we' are.

There are endless reams of paper and keyboard strokes spilled over neighborhoods. Someone will be along shortly to recommend Wicker Park. Or Logan Square (the new Wicker Park) or whatever.

It doesn't matter. Every corner of the city is different, diverse, and challenging. You could live in one spot happily your entire life and miss out on entire cultures just a few blocks over. The point is, don't expect to really settle in your first place. You'll move around multiple times before you find your place. Trust me. This is the one key thing Chicago has taught me.

Mostly your deciding factor is how much money you make and how much space you need. A studio in a ritzy neighborhood will set you back a grand or more. For the same price you can have a run down four bedroom in other parts, and likely be just as close to downtown.

Get a guide book. Pick out four or five neighborhoods that you absolutely must see - preferable ones as diverse from the other as possible, then go see them. That's the only way to get a real feel for things. After that it's just a matter of finding an apartment in your price range.

Good luck. If you do move here you won't be sorry. Chicago is possibly the best city in the universe.

And Chicago mefis rock.
posted by wfrgms at 7:23 PM on August 7, 2008 [2 favorites]

Adding to wfrgms' great comment above, a one-word piece of advice. Walk. You'll get a real sense of Chicago just walking across 2-3 neighborhoods.
posted by ferdydurke at 8:00 PM on August 7, 2008

I grew up in NYC (Manhattan) and have lived in Chicago for the last 10 years. As far as I'm concerned there's no contest - I like Chicago much better. It's cheaper [by a factor of 2-3 or more for housing], it has alleys for garbage, etc. You sum it up pretty well when you say "lower cost of living; fewer of the NYC annoyances but still a big, exciting city."

Don't underestimate exactly how much lower the cost of living is - if you're looking to buy a two bedroom condo in one of the the fun neighborhoods you'll probably pay about 1/2 the price of a studio condo in Manhattan. If you'd rather have an actual house (with a yard and everything) in those same neighborhoods that'll run you about the cost of a nice studio or crappy one bedroom in Manhattan.
posted by true at 8:05 PM on August 7, 2008

I asked a very similar question recently and got some fantastic responses. I'm moving to Chicago in the next year or so, and I can't wait. NYC might deliver everywhere 24/7, it might have more stars and more industry, but Chicago is truly a staggering, magnificent city.
posted by zoomorphic at 8:17 PM on August 7, 2008

Best answer: I am an East Coast-transplant who moved to Chicago 18 years ago and just never saw a reason to leave. Great cultural life, great food, so much to do, etc. You can certainly get out and explore the various neighborhoods (yes, Logan Square, Wicker Park, even Bridgeport and Pilsen). Chicago really is a city of neighborhoods, and every one is really different in tone and character. But mostly I want to second ferdydurke's suggestion and make it even more specific: walk up Clark Street. Start in the Loop and just keep going north. (I lived on the South Side for many years, so insert disclaimer here about how Clark Street isn't the "real" Chicago but still . . . it's a place to start). You'll go through the financial district, over the river, past the best restaurant in Chicago (Topolobampo! stop at the bar at Frontera Grill and get a margarita and squid ceviche), through the "ritzier" neighborhoods on the Gold Coast and into Lincoln Park. You'll pass through Boys Town and Lakeview/Wrigley Field (ugh, least favorite neighborhood but it seems to be quite popular among some folk). Keep going and you're in Uptown and Andersonville. It will take several hours, and it isn't the "whole" Chicago, but the weather is supposed to be beautiful and you'll see/feel more than if you were driving around.
posted by fiery.hogue at 8:45 PM on August 7, 2008 [2 favorites]

Oh and we have a meetup planned for next Wednesday... you probably can't make it, but just in case...
posted by wfrgms at 8:46 PM on August 7, 2008

It's pretty easy to be car-free in Chicago. We've got a decent public transportation system, a mayor who supports bike transit, and a couple of well-established car-sharing services (iGo, Zipcar). When you're looking for a neighborhood, consider proximity to an el line and grocery store (sometimes rare in the funkier neighborhoods). There are some suburbs that aren't serviced by the commuter trains, so if you're working out there, driving is the only option.
posted by hydrophonic at 9:27 PM on August 7, 2008

Just know that the weather here this weekend does not reflect digging your car out of ice everyday for a few months..
posted by melodykramer at 9:30 PM on August 7, 2008

In my experience, a bicycle is better than walking -- why walk when you can roll? I've not lived there in many years so I can't fill you in on much more than the various touristy posts, as all I've done in the years since I've left are brief touristy visits. But on one of those visits I rented a bike and it damn sure makes it a lot easier to cover the miles that fiery.hogue is recommending. You can be from from here to there and back again, eat dinner at the place that looked so interesting on the ride earlier in the day, and it's as good as walking in that you're close to the street, close to the beat, you can pause as you'd like to see what you'd like, it's not like you're on a bus or in a cab or even in your car, you're close to the pulse of it all, you're riding the pulse of it all. Chicago in the summer is my second favorite US city, just after Austin in the winter. I hope you have a time.
posted by dancestoblue at 9:34 PM on August 7, 2008

Also, as an East Coast transplant who plans to move back to the East Coast quite's what I miss...Amtrak. I really miss being able to zip to DC or Boston or Philly or New York within a few hours without having to fly. I don't know if you typically do this - or want to do this - but I feel like Chicago is kind of in the middle....with nothing else close by.
posted by melodykramer at 9:54 PM on August 7, 2008

I was born in Chicago, grew up in Wisconsin, and after spending a couple of years in NYC, I moved to Chicago for about 15. Although I loved and miss New York for what it is, I prefer Chicago for many reasons. In a nutshell, it's New York crossed with Midwestern sensibilities.

It's possible that you've been to Toronto. I know that Torontonians consider Chicago to be the closest analogue to themselves in the US.

My view of New York is that for most people, living in Manhattan just doesn't make sense, financially, logistically, or otherwise. So you're really comparing living in Brooklyn, for most people (say, Park Slope or DUMBO), with a lesser focus on the other boroughs. If you want to live in the City (i.e. Manhattan), and have the resources or need to do so, you probably already know this. For certain careers or lifestyles there may be no other choice. Go -- you have my blessing.

For others, though, Chicago is just as good and better in certain ways. The choice of neighborhoods is just as broad, and you even have quasi-urban/suburban options such as Evanston (my particular choice). There are world-class artistic venues and museums, universities, a lakeshore with a superb park to take advantage, housing options from three-floor walk-ups to gleaming lake-view skyscrapers, an excellent if imperfect transit system, a diverse economy, and on and on.

I would truly say that only major downside is the six weeks in the dead of winter, especially if there's snow. And it's the only time the city is truly treacherously "windy". (I'm not kidding when I insist that you invest in a good scarf, gloves, and long underwear.) But if you can hack that (hey, I grew up in Wisconsin!) the rest of the year is great. By contrast, I found New York's weather dull or even unpleasant in every season except autumn, when it was heavenly.

It is definitely a city where being carless is easily possible. I would still recommend having one, for various reasons (the odd furniture pick-up, for instance). But maybe you could use a zipcar service and manage as well. It puts an extra constraint on your neighborhood options, though. Most of the really funky areas are near enough to the "L" but commuting might require a bus ride, and the bus is adequate but nowhere as good as the "L". (And yes, it is the "L" and not "the El" -- that's what NYC has!) Plenty of people bike to work or just up and down the lakefront and so forth, so that's an option, too, but again may limit where you live.

It is true that about the only urban place you can reasonably get to from Chicago is Milwaukee (including via Amtrak), and Milwaukee is just like Chicago Lite in a lot of ways, so it really isn't a change of venue. If you have or can get a car you can get out to places ranging from Madison, Wis. to Ann Arbor or parks like Starved Rock -- not to mention the major concert venues around here which are in the far south suburbs and Wisconsin respectively. (Of course lots of people carpool.)

Stuff that Chicago has that New York doesn't include the bascule bridges downtown, Navy Pier, sailing on the lake, and architectural history including the birth of the skyscraper. (Nowadays both NYC and Chicago feel a tad outclassed by Dubai and various Asian capitals.) Obviously New York has a lot that Chicago doesn't, or Chicago has something that's only "almost" as good. Case in point -- the Met vs. the Art Institute. We have no Guggenheim equivalent at all. The Gold Coast is similar in many respects to the Upper East Side,but we really have nothing comparable to the Upper West Side as a cultural settlement. But again, if that extra edge of being a top-tier "World City" is something you need, you'd know that already.

Good luck!
posted by dhartung at 11:48 PM on August 7, 2008

Yeah, you're going to just have to walk/bike/bus around and see if you dig it, but one weekend? Man, it took me three years to really enjoy being here, but now I don't want to leave.
posted by adamdschneider at 12:18 AM on August 8, 2008

Do it. I just moved from Chicago to San Francisco, and while the weather is much better here, there's just something about Chicago that I miss. It's...really an amazing city. As for neighborhoods, I'd avoid Wicker Park and Logan Square actually, I was a diehard Lincoln Square and Andersonville fan of luck!

Oh, I was car free for three years there. It's fine, public transit is good, and it's pretty bike friendly.
posted by gleea at 12:57 AM on August 8, 2008

Best answer: Born and raised in Manhattan, LOVE Chicago, would never go back. I disagree with esmeralda_jenkins though - you should check out the East Lakeview/Boystown area, and you should seriously consider living there. I've been living here for 5 years and it's by far my favorite neighborhood in Chicago.

Chicago is clean (at least compared to NY), the people are nice, things generally work, the cultural life is plenty rich for most mortals and in many ways more accessible than NY, and housing is affordable in most places. There's a great sense of city spirit and an almost small-town sense of community for such a big place. The city government, while flawed (ahem), makes quality of life a priority to attract residents. I always felt like NY, overflowing as it is, had more of a sink-or-swim mentality. I guess you could say that because Chicago is the "Second City," like Avis, it tries harder :-)

Places to go/things to do - take an architectural boat ride on the river downtown. Yes it's touristy; it's also awesome. Go to the Frank Lloyd Wright Home and Studio in Oak Park. Chicago is proud of its architecture and it will give you a sense of where that comes from.

Neighborhoods to walk around and think about living in: As I said, I think East Lakeview is the best for livability, fun, and convenience - that's a couple block radius around Belmont between Lakeshore and Halsted. Lively walking life with great transportation. If you want a good feel for the neighborhood, stay away from Wrigley Field and take a walk north from Belmont on Broadway (NOT Halsted, then cross to Halsted via Buckingham or Roscoe. There's a world of difference between the area around Wrigley, the Halsted Boystown scene, and the more mainstream community centered around Broadway.

Other suggestions above are good: Lincoln Square and Andersonville are nice. Wicker Park and Bucktown cater to a younger crowd but are worth looking at. If you want more of a city life you can live downtown, but it tends to be more expensive, and I prefer the quality of life and peace and quiet you can get elsewhere. You could check out Evanston (where Northwestern is) or Oak Park as more suburb-y places that are still plenty diverse and lively.

You're living in upstate NY so cold shouldn't be a problem, but a lot of people will try to scare you away from Chicago because of the weather. Just buy a great coat if you don't have one already and you'll be fine.

In short, DO IT. I love it here.
posted by walla at 5:27 AM on August 8, 2008

You're going to get very varied advice on neighborhoods. If you want funky/artsy instead of upscale, then the super-yuppie Andersonville/Lincoln Square will not suit you. Logan Square, Pilsen, or Ukrainian Village might be a better fit. The thing about neighborhoods in this city is that you just have to hang out in a few and figure out where you feel most comfortable. I'm a bike commuter and find this city to be fairly bike friendly. I also have no car (but use Zipcar) and don't really miss having one. There are lots of great vegetarian restaurants here too.
posted by smich at 7:30 AM on August 8, 2008

Response by poster: Thanks to fiery.hogue for the specific advice about what to do while I'm in Chicago. Thought I marked that answer as the best, I'd still be interested to hear from anyone else about what I should do over the weekend in Chicago to get a sense of whether I'd want to move there.
posted by jejune at 9:04 AM on August 8, 2008

You need to look on and find out what neighborhood festival is going on. I'd recommend going to one of them. As my friend said at one last weekend "this is why I live in Chicago"

These things are notorious boozefests though, so it might put you off Chicago. Where I live (in uber yuppie Lincoln Park) everyone I know is about sports (this is why I moved here instead of NYC) all the time. There's a bar on every corner, mostly with big plasmas and chicken wings.

But its so diverse that you can go down the street 10 feet and go into a old man's dive bar or a into a grunge rock bar.

Gross generalization ALERT: I'm in my 20s and spent a lot of time in Manhattan with mostly yuppies in both Chicago and Manhattan. Manhattan people (to me) tend to have their live filled with 'dates', and these are pretty packed days. Friends in Chicago tend to just drop in and hang out. I noticed more people are up to doing things on their own in NYC (like eating out by themselves). It could be my sheltered friends, but I think there's some truth in it. Also, don't discount the fact that you can drive to a grocery and fill up your trunk with food.
posted by sandmanwv at 1:18 PM on August 8, 2008

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