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What are the "can't miss" things to see in Chicago?
July 2, 2009

Dear Cecil:

Let's say you have two days to see Chicago … and by you I of course mean me.

My sister and I are coming to Chicago for the weekend. It was my choice (the trip is a birthday present) and I picked Chicago because I've heard good things about the city and have never been there. We will be there all day Saturday and all day Sunday, staying in a hotel on Michigan Avenue. We fly home Monday noon-ish.

So what do we do? What are the "can't miss" things to see in Chicago? I know we can't really put a dent in it in two days, but that's all we have. We are more the shopping-strolling-museum-tours-sidewalk-cafes-glasses-of-wine type, as opposed to the sports-loving-club-hopping types. Suggestions for places to eat would be appreciated as well.

— Jodi, via the Straight Dope Chicago Message Board

Cecil replies:

Jodi, I have to be honest … I may not be your best source on this. I'm not opposed to sidewalk cafes, glasses of wine, and that whole drill, OK? But let's face it, you could do that in Vancouver, or Sydney, or any of about 200 other gentrified locales I could name. In Chicago, on the other hand, my feeling is you want a little grit. Don't get me wrong. I'm not talking about your New York 1975 scuzzball subway graffiti heroin addict type of grit — I mean, Jesu Cristo, I got some kinda standards. I'm just saying one needs to acknowledge urban reality, which has a charm, even — dare one say it? —  a beauty all its own. So accept the following for the quirky compilation it is. And yes, they're my quirks, no denying it. If others have thoughts on the subject that aren't completely inane and care to post them on the SDCMB, maybe later I'll post a digest of everybody else's quirks. But today you're dealing with mine. 

Eat a hot dog. Fine, you can substitute some other quintessential Chicago foodstuff, but I've done plenty already to boost the Italian beef industry. In any case I don't want to dwell on the food, critical though that is. (I shouldn't have to say this in re hotdogs, but just in case: No ketchup.) Rather, I speak of … well, ambience isn't an expression one willingly puts in the same sentence as hot dog. But one has to acknowledge the importance of environmental considerations. What you want is an establishment devoid of pretension. Two choice examples in this respect:

(1) Hot Doug's, 3324 N. California. As Chicago hot dog stands go, Doug's is relatively new, but it's already attained legendary status. (Sample review: "Sweet holy mother was that the best sausage I've ever had.")  The place is, to say the least, idiosyncratic. It's only open from 10:30 a.m. till 4 p.m., and the exquisite duck-fat fries are available only on Fridays and Saturdays. It's also situated in what has to be the most nondescript locality on earth, or anyway outside northwest Indiana, surrounded by parking lots, industrial buildings, and a Com Ed substation. (One of the industrial buildings houses WMS Gaming, the arcade game company that gave the world "Mortal Kombat," but I can't say this knowledge noticeably enhances the culinary experience.) People go to Doug's solely for the food — and boy, do they ever. At noon the line wraps around the building, even in the rain.

(2) Byron's, 1017 W. Irving Park. More old-school than Doug's, Byron's has several locations, but I prefer this one for reasons that will be obvious when you visit: it's basically a shack surrounded by a parking lot, the seating consisting of a few picnic tables. In the background you have an el station with trains screeching around a curve and a recorded voice periodically declaring "DOORS CLOSING" amid the general urban din. The hot dogs are very good, with the full array of desirable condiments. (I skip the cukes myself, but don't omit the celery salt.) I don't want to oversell the place. But as Chicago eating experiences go, this is about as pure as it gets. 

Perhaps you're not a hot dog person, though. One accepts that.  Tell you what.  Try Margie's Candies, 1960 N. Western, the interior of which hasn't been altered in any significant way since 1952. When people speak of old Chicago, this is what they mean. You can, if desired, obtain an actual meal at Margie's, but for most it's more of a dessert place. Ice cream on a plastic chair on a steamy summer evening — if that doesn't work for you, there really is no hope.

Take in some drumming. There's something about city living that makes you want to pound on things. Well, maybe not you, Jodi. But definitely guys. This impulse can have adverse consequences. When appropriately channeled, however, the results can be impressive. I don't know if the conga players still do their thing out on Promontory Point in Hyde Park, although it was a summer ritual for years. But you can definitely find the bucket boys — indeed, depending on circumstances, you may be hard put to escape them. Where they'll turn up on any given day is difficult to predict, although you can generally count on seeing them in the vicinity of Wrigley Field and the Cell during home games. The bucket boys are controversial. They play, as the name suggests, buckets — specifically, overturned five-gallon plastic buckets of the sort paint comes in. The equipment may suggest amateurishness. Not at all. The bucket boys play in perfect coordination, their rhythms and stickwork intricately choreographed — and there are squads of these guys. They're also extremely loud and play for hours at a stretch. These last facts explain why certain parties, to put the matter bluntly, think the bucket boys suck. But you don't have to spend all day listening, Jodi; you're a tourist. Give it 20 minutes. An experience not to be missed. 

Do a lake thing. I express this in general terms because there are about 500 lake things, all of which have their points, but with only two days you need to prioritize. Nothing personal, Jodi, but I'm guessing skinny dipping at North Avenue beach is probably not your thing. Sex on the rocks no doubt is also out, because you did say you were being accompanied by your sister, and anyway they tore out most of the cool (if surprisingly fragile) rock revetments years ago and replaced them with soulless concrete. However, dawn can still be relied on. This time of year you need to be out there at 5 a.m., 5:30 latest — don't be a wuss. Oak Street beach. Maybe a cup of coffee in a styrofoam cup. Behold the sun bubbling up to the east. Savor this. Behind you: towers, complexity, neurosis. Before you, a sight upon which hunter-gatherers gazed, assuming you can mentally Photoshop out the Navy Pier Ferris wheel.  Then, what the hell, strip to your skivvies and have yourself a splash. 

Do a river thing. Your options here are fewer, because the river as center of the Chicago experience isn't an entirely mature concept. So what? This is your chance to get in on the ground floor. My idea would be renting a kayak, but I concede this may not be everyone's cup of tea. Plan B: Get yourself invited out on a party boat. I recall a delightful downtown river cruise some years ago during evening rush, a big band playing jazz in the stern, a plastic cup of wine in my hand (see? I know how to be sophisticated), as I gazed up at the harried office workers dragging themselves to the commuter stations on the bridges overhead. Perhaps it's sinful of me to think so, but life doesn't get much better than that. Granted, this sort of thing is tough to arrange on short notice, unless you went to Notre Dame, the alumni of which seem to organize most of these events. Never mind, on to Plan C: Chicago River architecture tour.

Fireworks. I don't care if they're a cliche. I like fireworks, and they never fail to impress out-of-towners. The major event is the 3rd of July show on the lakefront — the date may strike you as odd, but this is a city that celebrated the 400th anniversary of Columbus's arrival in 1893. It's tough to beat, assuming you don't mind rubbing elbows with a million other sparkly-lights-and noise aficionados. For something a little more intimate, you can take in the regular twice-a-week barrages at Navy Pier, when it's just another ten thousand people and you.

Do some streetwalking. That didn't come out right. What I meant was, just stroll around. If you're the type who requires a guide for this purpose, the Chicago Architectural Foundation offers walking tours of the more notable districts. Otherwise you can risk it on your own. Since you've only got two days, you'll want to take in Michigan Avenue and Dearborn Street. (Definitely Dearborn Street. Start at Adams and walk south. Keep your eyes open. Look up.)

Eventually, though, you need to get out to the neighborhoods. Milwaukee Avenue. 18th Street. Drexel Boulevard. These are among the world's great city streets. If you want to ease into it — one recognizes that Chicago without preparation can be a bit of a smack in the face — amble along the general line of Webster Street through the Lincoln Park neighborhood. Start at, oh, Ashland Avenue, where it's still semi-industrial, and head east. Pretty, isn't it? Conclude at Clark Street. Get a frozen yogurt at Treats, 2224 N. Clark. Come on. Even if your idea of urban is Portland, Oregon, you gotta like this.

Eat at a diner. Not to fixate on the low end of the food scale, but you really ought to try one of these places, because my guess is their days are numbered, crowded out by encroaching megalopolis. The food is basic, the decor minimalist (a counter, a row of stools, maybe some quilted stainless steel), your fellow diners a slice. I spent a lot of time in the Diner Grill, 1645 W. Irving Park, during a trying passage in my life, and heartily recommend it; but I have to say the ultimate diner for me remains the White Palace Grill at Roosevelt and Canal. I used to drive there early in the morning with a friend who was an Amtrak hostess and had to get dropped off at the ready room near the yards. Beautiful woman, scary smart, stubborn as all getout … excuse me, we were talking about the grill. You approached from the east on a viaduct that crossed a vast expanse of railroad tracks. There was virtually nothing else around in those days; you felt you were at the edge of world, the diner your refuge. Now the place is surrounded by Bank of America and Whole Foods. Perhaps in this affluent context you'll find a diner merely incongruous. If you think you have the imagination, though, come out early in the morning, when traffic is light and you can hear the diesels whine. Take your cup of coffee, look out the window at the sun glinting off the rails, and contemplate a city that's now all but gone.

— Cecil Adams
Photo by Pat O'Neil

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