WANTED: Chicago's version of Portland's Goose Hallow (Lincoln, Brooklyn: broker, neighborhood)

[gatorman]

From Chicago, lived in PDX four years.

Lincoln Park is your best bet.

[Avengerfire]

Seems more like Lincoln Park and East Lake View with a bit of Uptown, Edgewater, and Rogers Park thrown in. Of course without the hills and the street cars...

I would go for Lincoln Park and Lake View.

[brinegar312]

you guys all rock!

[Lookout Kid]

There are parts of Lincoln Park and Lakeview that are not very fratboyish at all. Both are very large areas with a lot of complexity.

Lakeview is HUGE (over 80,000 people), and it's hard to take it all in at once. It has many sub-areas without strong borders. But the "Bourbon Street" part of Lakeview is also the sportiest part, and that's "Wrigleyville", or the section of Lakeview surrounding Wrigley Field. "East Lakeview" is centered around the lake and a commercial strip on Broadway. "Boystown" is sort of the next layer west, and is centered along a commercial strip on Halsted. "Wrigleyville" is centered around a strip of bars, restaurants, etc. on Clark Street (and of course, Wrigely Field itself). And then there's the trendy Southport Corridor on Southport.

Lincoln Park is equally complex. Parts of eastern Lincoln Park (along the park) remind me of the Upper West Side in New York. DePaul is overrun with students, but is also a very pricey and charming residential area. There is a commercial strip on Armitage between Halsted and Racine that has many fancy boutiques (and it wraps north along Halsted as well). This area is a bit less studenty, but there are fewer and fewer rentals south of Armitage. There is a large section of gaudy teardowns south of Armitage that is sort of becoming the "New Money Gold Coast", though one of the very "Old Money" Pritzker girls just built herself a modernist mega-mansion there.

Old Town is basically centered along a commercial strip on Wells Street just south of North Avenue. You have to be careful searching for places in Old Town because Cabrini Green is just to the west (or what's left of it anyway), and realtors and apartment agencies keep calling stuff "Old Town" when it's really a bit too far west. But it's a really great part of the city if you can afford it. Some of the houses are very charming, as are the blocks near DePaul that haven't been too affected by teardowns.

If you want to walk to work downtown, I'd suggest Old Town, the Gold Coast, River North, the South Loop, or the West Loop. The South Loop and West Loop areas (not actually part of the Loop itself) have newer housing, and are still lacking some of the basic neighborhood ammenities and feel. Personally, I prefer to be in a more established neighborhood. River North is pretty much an extension of downtown.

[Drover]

If the OP wants the sort of charming boutique-store and restaurant ambiance without the party atmosphere, I think we're missing the three most obvious recommendations: Andersonville, Lincoln Square and Roscoe Village. They're generally more toned down than even the non-fratboy parts of Lincoln Park and Lakeview, but without being boring. Of course none of these places are within walking distance of downtown, but I would encourage the OP to ditch that criterion because a) it's incredibly restrictive given the size of this city, and b) the city has a comprehensive public transportation system that can get you from most residential neighborhoods to downtown in a reasonable amount of time.

IMO Old Town is a little too buttoned-down and a little too "old money." The place just has a stuffy air about it.

[neonwattagelimit]

If you are looking for something relatively quiet, I would avoid Wrigleyville like the plague. As others have said, it feel like a giant, overgrown frat party. If you want to participate in the frat party sometimes - understandable, that - you could always take the Red Line over there from elsewhere on the North Side.

I'll second Drover's recommendation of Andersonville, or perhaps nearby Edgewater (which is where I live). It's quiet, but still has enough things to do to keep you occupied. Plus, if you live in a part of the neighborhood with easy L access (once you get west of Ashland, you could be looking at a hike to the Red Line, it's nice over there but if getting downtown is important to you, I'd avoid it), you can still go downtown, or to Lakeview, or to any number of ther places fairly easily.

The biggest downside to this area is that, even if you're close to the L, getting downtown will take a while, usually around forty-five minutes for me, though it depends on where you're going and how far you are from a train station (I'm very close to one). Lately, it's been taking a bit longer, what with all the construction on the subway tunnel, but they say that will end in October..famous last words. This hasn't bothered me much - my commute where I used to live was over an hour, so it still seems like a reprieve - but if you're used to rolling out out of bed and being at work in 15 or 20 minutes, it could take some getting used to. It's a great neighborhood, though.

[Lookout Kid]

Originally Posted by Drover

If the OP wants the sort of charming boutique-store and restaurant ambiance without the party atmosphere, I think we're missing the three most obvious recommendations: Andersonville, Lincoln Square and Roscoe Village. They're generally more toned down than even the non-fratboy parts of Lincoln Park and Lakeview, but without being boring. Of course none of these places are within walking distance of downtown, but I would encourage the OP to ditch that criterion because a) it's incredibly restrictive given the size of this city, and b) the city has a comprehensive public transportation system that can get you from most residential neighborhoods to downtown in a reasonable amount of time.

IMO Old Town is a little too buttoned-down and a little too "old money." The place just has a stuffy air about it.

I agree with that completely. But by naming closer-in neighborhoods I was reacting to the OP's desire to be close to downtown. I love Andersonville, Lincoln Square, and Roscoe Village--but I wouldn't want to do that walk! And the commute via train is pretty long to each of these areas. But the same can be said for the distant corners of Lakeview too, I suppose. If you're going to consider Southport, what's another couple stops on the Brown Line, right? I think the OP needs to get around the North Side to appreciate the sheer magnitude of Chicago... There are five or six Bostons in one Chicago.

Old Town is pretty buttoned-up. It used to be a large hippy enclave, but 97% of that has moved on to hipper environs in the past forty years. The "Pipers Alley" of today is no place to buy a hash pipe...

[aragx6]

I still think Wicker Park makes a lot of sense for you in that it has plenty to do, is far closer to downtown than Andersonville or similar

[brinegar312]

One comment on Wicker Park, however. I am not a hipster. I avoid hipster-areas in most cities I go to. I have heard Wicker Park is kinda like a Williamsburg, Brooklyn. Is this true?

Originally Posted by aragx6

I still think Wicker Park makes a lot of sense for you in that it has plenty to do, is far closer to downtown than Andersonville or similar

[neonwattagelimit]

Originally Posted by brinegar312

One comment on Wicker Park, however. I am not a hipster. I avoid hipster-areas in most cities I go to. I have heard Wicker Park is kinda like a Williamsburg, Brooklyn. Is this true?

Oh yes.

I'm a former New Yorker and I'm quite familiar with Williamsburg. I actually view being similar to it as both a good and a bad thing. I don't think you'll feel out of place there if you're not a hipster - it's not that bad - but Andersonville/Edgewater is definitely less hipsterish (though there are some around here). But Wicker Park is much closer to downtown. So...your call!