Chicago – Kick-ass Architecture and Hot Dogs Too
Places 16 years ago No Comments

contributed by JP Anderson [Chicago native / restaurant guru / champion of lefty rights] 

There’s a reason Ol’ Blue Eyes called Chicago his kind of town. It’s the kind of place you can’t help but love: a city that’s sophisticated and worldly, but with genuine blue-collar roots and a melting-pot population of every race and color. The terrain is flat and unexciting—but then you come face to face with the jewel of Lake Michigan. The winters are brutally windy and mercilessly cold—but then spring comes, and it’s like a miracle. Chicago’s got Wrigley Field and deep-dish pizza, Second City and Charlie Trotter’s, and, for us Plinth & Chintzy types, an incredible architecture and design scene. From the Sears Tower to a slew of monumental skyscrapers and the brand-spanking-new Millennium Park, Chicago is a place definitely worth road-tripping to. Come on up and I’ll show you around.

The Lay of the Land
For a bustling metropolis of 3 million-plus, Chicago is a snap to navigate. Just a couple things to remember: Lake Michigan is always, always East. Plus, the streets are laid out on a very straightforward grid system (as Homer Simpson would say, “mmm, right angles…”), so it’s nearly impossible to get lost. Well, OK, it’s possible, but we Chicagoans are a friendly lot, so you can always just stop one of us on the street and ask for directions. Ready to start walking” Grab your parka—hey, you’re the one who wanted to visit in November—and let’s conquer this toddlin’ town.

Cool Buildings & Other Stuff Worth Seeing
The Great Fire of 1871 may have destroyed much of Chicago; the tragedy’s silver lining was that the monumental project of rebuilding the city attracted some of the nation’s most ambitious architects. As a result, the city boasts some of the greatest buildings in the United States. From Daniel Burnham and Louis Sullivan to Mies van der Rohe and Frank Lloyd Wright, we’ve got ‘em all.

Your best way to take in these impressive structures—which range from the Burnham’s Reliance Building at 32 N. Lasalle St. (the world’s first steel-framed building) to the jet-black monolith of van der Rohe’s IBM Building (just north of the river on State Street)—is to take one of the comprehensive tours offered by the Chicago Architecture Foundation ( Walking tours are offered along themes like “Historic Skyscrapers” and “Modern Skyscrapers.” My advice” If you’re visiting between May and October, forget all that exercise and sit your fanny down in one of the foundation’s boats for one of the thoroughly enjoyable architectural boat cruises, which offers a truly unique perspective of the city’s buildings from the Chicago River. You’ll also probably be tempted to visit the Sears Tower ( (S. Wacker Dr at Adams St), the tallest building in the world until 1997, but the views are just as impressive from the John Hancock Building ( (875 N. Michigan Ave.), and it’s not as much of a schlep.

Millennium Park. ( Locals are still buzzing about this expansive public space, which opened in July of 2004 after years of delays. The verdict” This baby was worth the wait, showcasing several striking art installations by some of the finest artists working today. The biggest crowd-pleaser is Cloud Gate—which locals have fondly nicknamed “the Bean”—a massive, 66-foot-wide, 33-foot-high sculpture by Anish Kapoor that reflects the skyline in a seamless, gleaming surface of more than 100 stainless steel plates. Then there’s Spanish sculptor Jaume Plensa’s Crown Fountain, two 50-foot towers on which faces of everyday Chicagoans are projected. During the summer, every 12 minutes the faces pucker like gargoyles and spout water from their mouths, much to the delight of the kids romping below. Hot-shot architect Frank Gehry contributed two pieces: An outdoor band shell that boasts a lattice-work of speakers attached to arching metal beams that extend far out onto the broad lawn (which makes for some serious surround-sound); and a bridge—his first—that snakes back and forth from the park across busy Columbus Drive. It doesn’t lead anywhere in particular, but it’s very cool—and that’s all that counts, right”

Art Institute of Chicago. ( If you hit one museum while you’re in town, make it this one. Highlights include the stunning Impressionist and post-Impressionist collections (go ahead and do your best Ferris Bueller imitation in front of Seurat’s “La Grande Jatte”), plus Marc Chagall’s stained-glass “American Windows” and Grant Wood’s “American Gothic.”

Oak Park

World-famous for its dozens of Frank Lloyd Wright-designed buildings, this west suburban town 10 miles west of the Loop (pleasant 20-minute ride on the Green Line train) is Mecca for architecture nuts. Take a tour of the Frank Lloyd Wright Home & Studio (, which Wright built in the late 1800s and which is an inspiring example of the Prairie School style, with its use of interior light, open spaces and low, horizontal structures. Check out the play room Wright built for his kids, with a piano sunk into the floor by the staircase—genius. You can buy a handy brochure in the gift shop here that leads you on a walking tour of other Wright buildings in the neighborhood, including Unity Temple, Huertley House, and the Nathan Moore House.

If you can’t make it out to Oak Park, at least get down to Hyde Park and check out Wright’s Robie House (, a lovely example of Wright’s Prairie School style. While you’re in the neighborhood, stroll through the campus of the majestically gothic University of Chicago. Just don’t wander too far off campus; the areas surrounding the university are not particularly safe, especially at night.

Extra Credit: Pullman

If you’ve got the time and some wheels, take the drive down to Pullman (, a fascinating turn-of-the-century community on the far South Side built by railroad magnate George Pullman in the late 1800s. It’s like something from another world, all brick streets and old Victorian rowhouses—and amazingly, all 900 of the original homes are still intact. Driving around this quiet neighborhood, you’ll find it hard to believe you’re just a few miles outside the city.

Design-y Info

One of the most impressive structures along the river is of particular interest to design folks—the gargantuan Merchandise Mart (, whose 4.2 million square feet space houses 600 showrooms of home furnishings open to designers only. Did I mention that this place is huge” I’m not kidding—it’s the second largest building in the country after the freakin’ Pentagon. It even has its own zip code. Huge. HUGE.

If you can find your way out of the Mart, head north (hint: away from the river) and you’re in design heaven. The River North neighborhood is chock full of boutiquey storefront showrooms full of glittering tiles, sumptuous floor coverings, and uber-stylish furniture. Also in this ‘hood—on Franklin Street just south of Chicago Avenue, right under the El tracks—you’ll find some of the city’s finest art galleries, from Spencer Weisz and Aldo Castillo to Kass Meridian and Judy Saslow.

Anybody Hungry”
I tell ya, we Chicagoans know how to eat—how else do you think we survive the winters” We’re darn passionate about our favorite foods, too, from deep-dish pizza and hot dogs to sensationally soggy Italian beef sandwiches. And don’t even get me started on the amazing array of ethnic eats around the city, from tongue-tinglingly authentic Mexican in Pilsen on the South Side to Korean barbecue in Uptown, Swedish bakeries in Andersonville, Polish hangouts in Wicker Park—you name it. Want to get a good taste of the city’s best eats” Leave the diet at home and follow me.

Lou Malnati’s. ( Forget Gino’s, forget Giordano’s, and don’t you dare set foot in Pizzeria Uno. The best Chicago-style deep-dish pizza is at this locals’ haunt, which has dozens of restaurants around the city, including one conveniently located just two blocks north of the Merchandise Mart (and across the street from my office, thank you very much). Tangy, sweet sauce, firm, buttery crust. Damn good. The thin-crust is some of the best in the city too, but if it’s your first time, go with the deep-dish.

Mr. Beef. ( Another River North fave not far from the Mart and all the fancy galleries, this is a classic. Absolutely no atmosphere to speak of—seating is at long communal tables in a room so industrial it could be in a prison—but the gruff guys sweating it out at the grill behind the counter turn out a mean Italian beef sandwich.

The Wiener’s Circle. ( There is nothing, and I mean nothing, like a Chicago-style hot dog laden down with tomato, sport peppers (spicy jalapeno-like things), celery salt, mustard, onions and neon-green relish—but never with ketchup—on a poppy-seed bun. The best ones are at this Wrigleyville hangout, which stays open till 5am on weekends, where you get the benefit of being berated by the sassy, streetwise staff when you step up to the counter (hint: be ready to order—and be ready with a comeback when they start tossing barbs your way). If you’re craving a dog downtown, the next best thing is Portillo’s ( (kitty-corner from the Hard Rock Café), which has awesome dogs, sloppy-good Italian beef sandwiches, and lots of other fast-foody options.

Lou Mitchell’s. ( One of my faves downtown is this old-school joint near the Sears Tower, where bouffaint-haired career waitresses—think Flo from “Alice”—deliver fluffy omelets, pancakes and sausage to suits and tourists. There’s usually a wait, but management softens the blow by handing out donut holes and OJ to those in line. Gotta love it.

Wow Bao. ( This is a great, cheap Asian place to get a quick bite if you’re shopping in Water Tower Place on the Mag Mile. The menu features tasty, exotic options like pad thai chicken salad with zesty, kicky vinaigrette dressing, but the specialty is bao, which are steamed buns stuffed with savory fillings like pork, black beans and kung pao chicken. Not a great idea if you’re counting carbs, but the price is right. The fresh-brewed ginger ale has a nice kick, too.

Green Zebra. ( Lest you get the impression that all Chicagoans eat is pizza and processed meat, I’m including this hot-hot-hot spot on Chicago Avenue in the growing West Town neighborhood. Upscale vegetarian small plates fare like x and y, serene, intimate surroundings, and impeccable service equal the year’s best new restaurant (you heard it here first!).

Blackbird. ( If you’ve got expense account bucks to burn, check out this modern, minimalist standby on Randolph Street, whose sleek white and gray décor and impeccable new American grub from chef Paul Kahan draws a trendy crowd of foodies. Too spendy for you” Mosey next door to avec (, by the same owners, for scrumptious small bites and quartinos of wine in a long, narrow room with cedar plank walls and ceilings. Too cool.

Let’s Get Drinks
After a long, hard day of soaking up Chicago’s world-class sights, architecture and design scene, you deserve to kick back and pop open a cold one. Whether that means a beer in a relaxed local pub or martinis and a swank singles scene, well, that’s up to you. These are some of my favorite watering holes in town.

The Pepper Canister. ( Smack dab in the middle of the River North design district, this convivial Irish pub forgoes kitsch in favor of contemporary, comfortable style, with warm wood accents and a long, inviting bar where you’ll find not just Guinness and Harp on tap, but Magner’s Cider as well. A perfect spot for winding down—good basic bar food menu, too.

BIN 36. ( The wine lover’s wine bar, this open, airy space has a mile-long list of vinos by the glass (all with user-friendly descriptions), plus a brand-new cheese bar that local foodies drool over.

NoMI. ( Everybody yammers on about the view from the Hancock Center’s Signature Lounge (, but we say leave it to the tourists—this fab restaurant and lounge in the Park Hyatt hotel has it beat by a mile. Not only is the 7th floor view of the Mag Mile incredible, but the space also boasts an incredible collection of contemporary art, including a 40-foot Dale Chihuly glass installation that snakes above the dining room.

Base Bar. ( This just-opened hot spot in the Hard Rock Hotel is worth checking out for several reasons. The location is prime Michigan Avenue just south of the river, and the crowd’s as sceney as it gets in Chicago, with divas, rock stars and a whole lot of wannabes hanging out till all hours. Most important, the setting is the historic 40-story Carbon and Carbide building, one of Chicago’s most famous skyscrapers.

Hopleaf. ( A few miles north of downtown, this cozy tavern just might be the best place in the city to grab a beer—it’s certainly one of my favorites. The selection of ales, lagers, and stouts is out of control, with more than 200 beers (mostly Belgian), and the food menu is sophisticated and satisfying, like steamed mussels, x, and y. But it’s the happy, Bohemian mix of locals that really makes the place what it is.

Charge It!
Shopping in Chicago is a blast—there’s an amazing selection of shops to browse through, and there are definitely some great bargains to be found. Here are the best places to use that charge card.

Michigan Avenue. There’s a reason they call this stretch of street north of the river the Magnificent Mile: From Water Tower Place to Neiman Marcus, Nordstrom, and flagship stores from Gap, Crate & Barrel, Banana Republic, Pottery Barn and Apple, you can find just about anything you’re looking for here.

Oak Street. Tonier than Michigan Avenue to the south, this is where all the chichi boutiques are, from Bang & Olufson to Jil Sander, Prada, Barney’s and Versace.

Wicker Park. If you’re feeling funky, head to this artsy neighborhood a couple miles northwest of downtown, where Chicago’s hippest designers show their stuff in stores like P.45 (, Apartment No. 9 (, and Tangerine ( Start at the bustling intersection of North, Milwaukee and Damen, and you’ll stumble onto some real finds.

Southport. More mainstream than Wicker Park, more boutiquey than Michigan Avenue, this street a half mile due west of Wrigley Field is becoming a real shopping destination for trendy local professionals, with cool casualwear stores like Krista K (, Red Head (, and—shameless plug—Jake (, owned by my buds Lance Lawson and Jim Wetzel. These guys carry an awesome line of upscale jeans and T-shirts for men and women, from Joie and Joe’s Jeans (I never take mine off) to Serfontaine, Earnest Sewn and Yanuk—and they’ve been highlighted everywhere from Daily Candy to Lucky and the New York Times. Be sure to tell ‘em I said hi if you stop in.

Where to Stay
So you’ve shopped, you’ve eaten, you’ve drunk—heck, at this point you may BE drunk—so where are you going to crash” The problem isn’t finding a room, it’s choosing from the many fab options that downtown Chicago has to offer. From no-budget dorm rooms to four-star suites, the city can accommodate pretty much any budget.

Hostelling International. ( OK, don’t cringe, this isn’t your typical crusty European youth hostel. Think spotless. Think prime Loop location. And think cheap, at about $30 per night. For impoverished travelers, this is truly a stellar option.

The Drake. ( Chicago’s most famous hotel (and one of its more expensive), and with good reason—it occupies a stellar location at the north end of Michigan Avenue, with excellent views of the lake. It seems a little musty in comparison to its newer neighbors like the Park Hyatt, but still a classic.

Red Roof Inn. ( This Streeterville chain hotel is affordable and just steps from Mag Mile shopping.

Hotel Monaco. ( Charming boutique hotel in the Loop offers guests goldfish to keep them company in their rooms during their stay. Cute!

Days Inn Lincoln Park. ( Nothing special atmosphere-wise, but good rates and awesome location in the heart of bustling Lakeview.


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