It’s a city of firsts. The former Home Insurance Building, completed in 1884, was the world’s first ten-story “skyscraper.” In 1942, Enrico Fermi conducted the first controlled nuclear reaction on a squash court at the University of Chicago. And deep dish pizza made its first commercial appearance in 1943, when Ike Sewell and Ric Riccardo opened the restaurant now known as Pizzeria Uno.
But this city of firsts is in fact the Second City, a reincarnation of the Chicago destroyed by the Great Fire of 1871. As flames tore through more than 17,000 buildings, Chicago lost nearly one-third of its property value over an expanse of three square miles. But from the ruins, more modern constructions of stone and steel would be built—a movement that would set a precedent for urban development around the world.
Today, Chicago’s 2.7 million residents make it the third most populous city in the United States and the undisputed capital of the Midwest. Long an international hub for finance, commerce, industry, and transportation, Chicago is also a city of groundbreaking cuisine, beautiful natural spaces, and beloved sports teams—with one of the most iconic skylines in America.
So pack your bags. We’re going to the shores of Lake Michigan for the next three days.
Hey Yeah, I Wanna Loop Baby
Begin your weekend in The Loop, Chicago’s historic commercial center that borrowed its name from the surrounding loop of elevated train tracks. And while a scenic spin on the “L” will weave you through the downtown cityscape, Chicago is a town best discovered by boat. For ninety minutes, the Chicago Architecture Foundation will lead you on a riverboat tour through the city’s past, interpreting more than 50 buildings along the way (First Lady Dock, 112 East Wacker Drive).
But don’t set sail without an early morning visit to The Doughnut Vault, the nearby bank vault-turned-doughnut shop that has been feeding Chicagoans since 2011. There’s always a line for the cake, yeast, and old-fashioned varieties—so arrive early or risk finding empty shelves (401 ½ North Franklin Street).
Expect More, Bayless
With a name derived from the Native American word shikaakwa—meaning “wild onion” or “wild garlic”—it’s really no wonder that Chicago is a food town. And there are few chefs who have contributed more to the culinary scene than Rick Bayless, whose vibrant, traditional Mexican cooking has won him multiple James Beard Awards and the title of Bravo’s Top Chef Master.
Since 1987, foodies have flocked to Topolobampo and Frontera Grill, Bayless’ neighboring restaurants in the Near North Side. But XOCO, the most recent addition to the family, offers the same bold flavors at a fraction of the price. So feel free to treat yourself to a modern interpretation of Mexican street food, from the mouth-watering pork carnitas in the torta ahogada to freshly fried churros for dessert (449 North Clark Street).
Come Celebrate The Millennium With Newmannium
When Chicago was incorporated in 1837, it chose as its motto Urbs in Horto—a Latin phrase meaning “City in a Garden.” Nearly two centuries later, the Chicago Park District still oversees 580 parks, 26 miles of lakefront, 24 swimming beaches, and 16 historic lagoons. Chief among these natural landmarks is Grant Park, fondly referred to as the city’s front yard.
Spend the afternoon getting lost in this 319-acre expanse, enjoying the view of Buckingham Fountain and the vast collection at the Art Institute of Chicago along the way (111 South Michigan Avenue). Just don’t leave before strolling through Millennium Park, where the stainless steel exterior of Cloud Gate—the sculpture known as The Bean—offers a unique perspective of the city’s skyline.
Chuck, I Had A Double Burger
Bring the day to a close in the West Loop at Au Cheval, an elegant tribute to the greasy spoon and brainchild of chef-owner Brendan Sodikoff (of Doughnut Vault fame). The menu highlights inventive interpretations of classic comforts, from the fried housemade bologna sandwich to the crispy potato hash with duck heart gravy. But it’s hard to top the double cheeseburger—a simple medley of perfect ingredients that will haunt your tastebuds for weeks (800 West Randolph Street).
Smoque Gets In Your Eyes
The Chicago Cubs may be at the bottom of the National League Central Division, but don’t let that deter you from taking in a game at Wrigley Field, the team’s home since 1916. Although it’s the oldest ballpark in the National League, Wrigley has yet to see the Cubs—who last won a World Series in 1908—as world champions. But thanks to its intimate setting (and one of baseball’s last hand-turned scoreboards), Wrigley offers fans and foes an unforgettable trip back in time (1060 West Addison Street).
If snacks and beer are central elements of your baseball experience, consider pre-gaming at Smoque BBQ, a local landmark for meticulously prepared ribs, brisket, and other smoked treats (3800 North Pulaski Road). For post-game beverages, head uptown to Hopleaf, where the staggering Belgian beer selection will keep you busy all afternoon (5148 North Clark Street).
I Knew You Were A Goat When You Walked In
In 2008, Stephanie Izard made Bravo history when she became the first woman to win the title of Top Chef. And just days ago, Izard took home another prize—this time a James Beard Award for her brilliant cuisine at Girl & the Goat. From the adventurous (crispy pig face) to the classic (wood grilled broccoli), every dish at this West Loop favorite is simple, delicious, and inspired. And with a weekend kitchen that’s open until midnight, there’s plenty of time to wait if you don’t have a reservation (809 West Randolph Street).
John Hancock… It’s ‘Herbie’ Hancock
It may not be the tallest building in Chicago—the 1,451-foot Willis Tower still holds that title—but the John Hancock Center and Observatory boasts what might be the city’s best view. One thousand feet above Michigan Avenue, visitors are afforded a stunning 360-degree panorama that encompasses the surrounding skyscrapers, four states, and more than 80 miles on a clear day (875 North Michigan Avenue).
One hundred stories down, you could spend the rest of the morning exploring the swanky shops of the Magnificent Mile. But you’re much better off strolling North Damen Avenue in Wicker Park and Bucktown, where a mix of designer and delightful independent stores—ahem, home decor at Alapash (4835 North Damen Avenue)—offer a little piece of shopping paradise.
You Know I Want To, But I’m In Too Deep
It’s a conflict that has raged for decades—and one that will likely continue well past my lifetime. But no matter your stance on thin crust vs. deep dish pizza, there’s no reason you shouldn’t sample the local specialties.
A few blocks south of the Hancock Center in the Near North Side is Gino’s East, a Chicago deep dish legend that has lived up to its reputation since 1966 (162 East Superior Street). But for a slightly different (and to me, superior) take on the regional favorite, grab a table at Pequod’s Pizza near DePaul University, which has been serving its signature burnt-cheese crust for more than four decades (2207 North Clybourn Avenue).
We Bought A Zoo
Aid your digestion with an afternoon stroll along the Lakefront Trail, an 18-mile path that traces the edge of Lake Michigan. While sections of the trail will bring you to Soldier Field and Navy Pier, today’s destination is Lincoln Park, which at 1,208 acres is Chicago’s largest public park. Between the landscaped gardens, free year-round zoo, public beaches, and archery range, you’ll have countless activities to keep you occupied until dinner.
There’s no better place to bring the weekend to a close than The Publican, legendary chef Paul Kahan’s tribute to simple farmhouse fare. And if the fresh raw oysters, potted rillettes, and generally meat-centered menu aren’t tempting enough, imagine eating these mouthwatering dishes in an elegant, high-ceilinged European beer hall (837 West Fulton Market Street).
Not in the mood for a big meal? Grab some late afternoon picnic fixings from Publican Quality Meats, the sister sandwich shop and butcher across the street (825 West Fulton Market Street). One taste and you’ll understand why Kahan—also the chef behind Chicago gems Blackbird and avec—was the James Beard Foundation’s outstanding chef for 2013.
A Few Notes
Consider making your home base for the weekend at PUBLIC Chicago, a stylish—yet reasonably priced—Ian Schrager retreat just north of the Magnificent Mile (1301 North State Parkway). And your best bet for getting around? A trusty $20 three-day “L” pass—tailor-made for long weekenders and available at downtown CVS and Walgreens locations.
TITLE: The Chicago skyline, from the John Hancock Center and Observatory | FRIDAY: The Chicago River; an L station in the Loop; the Bean | SUNDAY: the view from the Hancock building; the butcher shop at Publican Quality Meats.