(Edited 13 June 2012 to add links)
I lived in Chicago for a solid 18 years, and in the following four (during which I spent 15% of my time traveling the world, 60% studying in Ohio, and 25% trying to get back), I've tried to go home as much as possible. Like a sea turtle returning to the beach of its birth, Chicago is the compass of my life. It's not too grandiose to admit; in fact, it's pretty literal. It's still the one place in the world I can find my way around, hobbled as I am with a poor sense of space and direction.
Here is my work-in-progress guide to my favorite place on earth.* It's going to be endless, so I've divided it into Places to Eat, Coffee to Swill, Actual Entertainment, Hang-Outs to Hang, and Generally Great Finds. It's taken me 22 years to make this list, so please give me a shout if you like it, hate it, or want to send me a royalty check and feature it somewhere prominent.
PLACES TO EAT**
My friend Niki and I started coming to Kopi on Saturdays in the fifth grade, and it's still something I look forward to whenever I'm home. Named for the Indonesian word for coffee, Kopi is sometimes misconstrued as a mere bean peddler, but in fact boasts one of the best vegetarian menus in the city. Its impressive espresso offerings sometimes eclipse its food in the press and local memory, but that's no insult, just a compliment to the drinks, which range from Red Tea sweetened with condensed milk to something lemon and frozen called a Dr. Pucker my friend Laura swears by. Don't miss Kopi's back-of-the-restaurant store, which features all kinds of jewelry, travel packs, books, and soaps from all over the world; its motto ("A Traveler's Cafe") is the opposite of lip service. This is the place to go if you're planning a trip, or wish you were. And if not, the wonderfully caffeinated Dirty Chai milkshake will always cheer you up.
My older brother introduced me to this 24/7 diner, and I wish I could say I've gotten here more often. The food is out of this world, the prices unbeatable within Cook County limits, and their mocha milkshake is the stuff of dreams (or insomnia). The perfect restaurant before or after a night at iO or the ballpark.
Another relatively recent discovery in my life, this restaurant caters campily to the gay community in which it's situated, and we're all luckier for it. Featuring flowery mixed drinks and burgers so huge they come with a serrated steak knife to help you cope, Mary's is staffed by genderqueer kings and queens of all kinds, and the menu reflects the overall Castro-esque ambience. I think there's a drink called the Fred and Ginger I've yet to try; my favorite burger is the black bean BBQ, which is topped with an onion ring.
So much has been said and written about this upscale brunch venue, but it's worth braving the weekend crowds to taste for yourself. I'm especially fond of their huevos rancheros (I think it has a classier name, but look for the omelet with cheese and veggies and plantains on the side) and stuffed berry french toast. They also make a brilliant grilled cheese sandwich with PEARS. Yum. Note that the newer Rogers Park franchise is usually less peopled than her popular brother.
This is really a n00b suggestion, since you've probably run into about a dozen of these if you've lived in or visited Chicago for more than a few days. Still worth a mention: great sandwiches with that devil-may-care Midwestern attitude towards caloric intake. Thank heavens.
COFFEE
I first came here with a "cool older friend" who was all of 23 when I was just a junior in high school, and now, at almost her age then, I can still vouch for its utter coolness. Right across the street from one of my favorite used bookstores and the cheapest known movie theater in the city, The Grind is the best place to kill a half hour before a hot date or chill after a guitar lesson at the nearby Old Town School of Folk Music. (Which of these did I do more often in junior high?)
Two words: frozen. capuccino. I don't know anywhere else that squirts sweet espresso out of whipped cream cans, but they do. They're in the same building as my scholarship foundation's headquarters, so I was here often. Solid coffee; I miss it.
A recent discovery, courtesy of my friend Katherine. Absolutely stellar roast: MCC actually supplies coffee beans to lots of "coffee shops" and cafes throughout the city. A lot of character, a little pretense, but a great place to meet a friend to catch up if you're in Rogers Park.
ACTUAL ENTERTAINMENT
Since baseball was never my jam, I didn't think there was anything in the Wrigle Field-oriented neighborhood west of Lakeview for me or my liberal arty friends. How wrong I was. If you enjoy laughter and feeling superior to the tourists who buy out overpriced Second City shows, iO is the only place to go. I almost hate to confess my favorite show, since it is in some ways still the city's best-kept secret, but TJ & Dave on Wednesday nights at 11pm are the best of the best at improvisational comedy and there is no going back to mediocrity after seeing them. That would be a downer, if tickets for this kickass show weren't so cheap. At $5, I can nearly always afford to go when I'm feeling in need of a laugh, but be sure to buy by phone or online well in advance, since they sell out EVERY WEEK.
Full disclosure: I interned here. The only reason I got the job, though, was that I'd spent the majority of Saturday nights during high school haunting this black box theater situated above a funeral home in the heart of Andersonville. Fantastic experience of late-night, dirt-cheap, in-your-face performance art, but don't let that label put you off. Their method of "60 plays in 30 minutes" is a surefire recipe for giddy weekend fun with an always-welcome philosophical aftertaste.
The Davis, Lincoln Square
An old-school, janky movie theater that I believe still has $7 matinees. Used to be even cheaper, with 2nd-run movies, but these days has upgraded to current blockbusters and the occasional foreign film. GET ON IT!
Chicago Cultural Center
I tend to duck in here after a summer day at Millennium Park or the Art Institute, as it's situated quite centrally and provides a beautiful, air-conditioned space with no admission fees (or at least, there weren't the last time I was there). There are often art exhibits and music shows, there's an overpriced cafe, and a killer gift store. It's also right across the street from the CPS/Mayor Daley arts school Gallery 37, where I took a sculpture class from 2005-2006.
The Annoyance Theater
Not unlike iO on paper, The Annoyance is an improv-based theater that also enrolls students in classes on everything from sketch writing to more serious acting. I've not studied here, but I love the Tuesday night double-header Chicagoland & Fishnuts. At $8, it's usually an unbeatable night of comedy, and the fact that it's a weekday really cuts down on the traffic. Low-key but stellar.
My favorite. The best of the best. There's nothing like them. I interned very briefly for these fine folks as well, but they really didn't need me. They do everything: write their shows, act them out, find the space, decorate it with wonderfully inventive and appropriate set dressing and steampunky props. Always, always worth the price of a ticket, which varies according to the theater space they're renting out. Can't wait for them to get their own building one day-- it might be soon, if their recent successes are any indication. (Seriously, just check out their killer website.)
HANG OUTS***
Another place I worked back in the day, this bookstore is an institution in the family-oriented (formerly Swedish immigrant) community that flocks to the area surrounding Clark and Foster. Although they primarily feature feminist, GLBTQ, and children's literature, the staff is that particular kind of well-read fabulous that you only really ever get with independent booksellers. You know, the kind the big box chains try to simulate with the smell of coffee and armchairs? This is the sort of place they wish they could be. It was also, last I checked, the largest independent feminist bookstore in the United States of America, and its welcoming but comfortable size is a true testament to the fact that this is the kind of local store far too frequently dubbed a dying breed. If you want to be a REALLY good person and support them as much as they deserve, you can order nearly any book in print from them if they don't have what you want in stock, and get it the next week.
What a find! Not the best choice for the cheapest among us, but nevertheless the perfect place for gifts of every price range. I think I got everyone in my family a Hanukkah or Christmas present from Galeria last year. The idea of the place is simple enough: artists rent space in the four-story brick building on a high-traffic sidewalk, and potential buyers can walk among clothes, paintings, and ephemera both populist and underground. There's a great selection of Chicago-themed goods, since all the artists are locals!
My favorite bookstore in the city, tied only with Women and Children First, and yes, they keep a spectacular blog. Jim Mall is one-of-a-kind, and even that phrase is far too commonplace to describe the character that runs this special, quirky place. You have to visit to understand. It's like a hoarder's attic, if the hoarder was a genius book dealer with a penchant for radical politics, cats, and typewriters. But the true treasure is, of course, the books. The people who work here know what's what, and they can help you find anything amidst the piles and piles of vanillin-scented tomes that lay, deceptively organized, all over the tight and winding corridors of this tiny storefront.
I used to shop here before I discovered Ravenswood Used Books (which is much closer to me), and it was usually worth the trek south. If you're living in Wicker Park, good on you, because since it became the gentrified hot spot for twentysomething migrants to Chicago, I've heard rent has gotten fairly impossible for us barely-employed postgrads. That doesn't detract from the glory of this bookstore, though the neighborhood is better known for its bar life, good weather craft fairs, and alt-music scene.
GENERALLY GREAT FINDS
Such lovely ladies, such reasonably priced haircuts. It's right by where I grew up, and I've been going to Emma and Alma so long that they not only remember how I wore my hair for prom, but also the years of me talking about it beforehand. Don't take my word for it: people love them on Yelp!
I only recently found out that my parents and their friends hung out here a bit as pre-parents in the eighties. Pretty weird, since my friends and I just discovered it last summer, when we were finally all 21. Super relaxed, kinda dirty, but in a good, underpriced way. I don't drink a lot, which jives with the low-down, intimate feel of the back room, where there is a real, working fireplace and board games. It's also usually quiet enough to have, say, a birthday party with your high school friends and play pool.
Pretty schmancy (that's "pretentiously fancy"). I've only been here once, but it's quite the experience. Made like a pseudo-prohibition-era dive, you have to knock on a secret door below a single light bulb half-hidden by wood planking to get in, and they'll ignore you if they're full. Once inside, it's a swanky affair with high-backed grey booths and upscale, crafted drinks reminiscent of the Jazz Age. Certainly worth a trip, but maybe reserve it for a special occasion.
*It's true that Chicago is where my heart lies, but for whatever reason, I find myself always leaving her. I guess that's for others to psychoanalyze...
**I'm a vegetarian, so all of these posts can only really comment on the veggie fare served at the listed restaurants, but I promise all are delicious, even to my carnivorous friends.
***This is code for "window shopping" and "we're broke but we can browse."
