The big Chicago post

We’re back from five days in Chicago, probably as long as I’ve spent there since I lived in the area for college 10 years ago, and what I say every time remains true: I like it more every time I go. I had a bit of a different plan this time around–I set out to explore some neighborhoods I didn’t know very well, maybe hadn’t even visited at all. It’s tough to overemphasize how much Chicago has changed since I graduated in 1999. A few years ago, I read an interview with Brooklyn native, ex-con and snooty hotelier Ian Schrager in which he talked about why he was expanding internationally: because after conquering New York and Miami, he could never dream of opening one of his mega-pricey boutique hotels in a place as gauche as Chicago. I feel like he might reconsider that today. Judge for yourself whether that’s a good thing or a bad thing.

Chicago, of course, is a city of neighborhoods, and this weekend, we were all over the place–as long as that place was the North Side. I’ve never really explored the South Side outside of the occasional White Sox game and a few trips to Hyde Park, the South Side’s ritziest enclave and home to the University of Chicago. Maybe I’ll endeavor to change that on future visits. In the meantime, here are a few rudimentary impressions from an admitted outsider, nabe by nabe:

River North
We stayed with our good friend Larry V. in this neighborhood, which Time Out Chicago this week called “our version of Times Square,” and they didn’t mean it in a good way. However, though you certainly can’t say one of the wealthiest neighborhoods in town is gentrifying, it’s changing nonetheless. The streets are still eerily empty after dark, but there are signs of life on the northern edge of downtown, including Graze, the terrific restaurant Time Out used as a vehicle to bash the land of Rainforest and Hard Rock cafés. (Their assessment is not entirely inaccurate; Larry’s luxe high rise boasts a Chili’s on the ground floor.) Despite the Times Square comparison, Chicago’s downtown is a lot more like New York’s Financial District, but like the Financial District, buildings full of condos and retail space are going up at a breakneck pace. Larry is two blocks away from a big, newish supermarket, and there’s a Whole Foods just a couple of blocks beyond that. And you can’t beat this neighborhood’s access to public transportation and the city’s other areas, as we found out during the trip. But the coup de grace? The skyline view from Larry’s balcony, where historic architectural landmark after historic architectural landmark are just part of the everyday scenery.

Boystown
Yes, Boystown. Larry may be the gay one, but my non-gay best man Chris’ swanky new pad here assured that we’d spend at least a little time in Chicago’s same-sex mecca. Chelsea may be more of a nationwide household name, but Larry prefers the scene in Boystown, and why not? New York does not erect (er, no pun intended) giant rainbow phallic symbols on every street in its gay village. After B-Fest, we hit the gayest Mexican restaurant in Chicago for the second consecutive year to enjoy some top-shelf Tex-Mex and more than a few mighty powerful margaritas. We did not go out afterwards. Truly, we are getting old.

Wicker Park/Bucktown
Oh, man, I was looking forward to this neighborhood, and it did not disappoint. It especially didn’t disappoint Melissa, who didn’t buy a single article of clothing anywhere else. In the very first shop we wandered into, a chatty hipster clerk helpfully informed us that his place of employment was the first fashionable store to open in the area a decade earlier, back when the whole joint was “ghetto.” All or part of that statement may or may not be true, but there’s no disputing that Wicker Park and Bucktown, which gently blend into each other, have a distinct Williamsburg vibe going today. If you like independently owned boutiques and “twee restaurants,” as a skeptical Chicago friend derisively called them, you’ll love this neighborhood. I’m certainly a fan of twee restaurants, so I can’t believe it took me so long to get here.

Lincoln Square
Now here was quite the pleasant surprise. Here’s a somewhat embarrassing fact for you: In four years of college and at least one visit every year since, I had never in my life been on the Chicago ‘L’ system’s Brown Line. When I kept seeing ads for Lincoln Square apartments in local magazines and alternative newspapers, I decided to remedy that situation. Lincoln Square is now one of my favorite neighborhoods in Chicago. Not terribly exciting, it doesn’t have to be–it reminded me a little of a slightly hipper Forest Hills. Chicago has a much higher crime rate than New York, and you often feel it in the air. Streets are emptier, traffic is more sparse, and there seem to be a lot of solitary people in hoods leaning against buildings doing absolutely nothing. But Lincoln Square felt very safe, easily safer than any other Chicago neighborhood I’ve visited. Clearly an old German neighborhood, it’s now home to a younger crowd, a cute little shopping strip and an incredibly comfortable coffee shop where we hid from the cold for more than an hour on the cushy couches in back.

Evanston
Sure, it’s not part of Chicago, but how could I skip my beloved E-Town? For the uninitiated, Evanston is just north of the Chicago border and home to Northwestern, my alma mater, not to mention the bad-film festival unfortunately scheduled for the end of January that I attend every year. This year, the films on tap were worse than usual, so I took a very long walk around the town I remember–or make that don’t remember. Evanston has completely changed. What was once an eclectic blend of urban and suburban on the outskirts of America’s third-largest city has become an eclectic blend of luxury condos and more luxury condos on the outskirts of luxury condos. This is not all bad. A few parts of Evanston that felt downright dangerous when I lived there are now crawling with students and yuppies and studded with cranes, cranes and more cranes.

Very often when I was in school, Chicago just didn’t feel right to me because I loved New York, and it just wasn’t New York. Walking through an area adjacent to Larry’s a few days ago, I mentioned to Melissa that I’d come down there a lot in college. “Why?” she said. “This neighborhood is lame.” And it was lame, certainly one of the duller ones we’d visited. But I immediately knew why I’d come down there so much: It reminded me of New York. I don’t know whether I’ve matured or the city has–probably a lot of the former and a little of the latter–but when I go now, I realize that Chicago doesn’t have to be New York. It’s great in its own ways, ways completely different from anything that makes New York special. Its architecture is beautiful and fascinating. Its neighborhoods are somehow simultaneously big city and small town. Its retail is more independent-minded than New York ever gets, when it isn’t far more chainy than New York ever gets. A few years ago, I would’ve been mystified that Larry chose to move there from New York, but now it makes a lot of sense.

But sweet Lord, it is cold. Is it ever cold. Maybe it doesn’t make that much sense.