It might be the “Second City,” but Chicago is too big to know in a lifetime, let alone over a weekend. So a quick visit to this sprawling Midwestern metropolis benefits greatly from a tight focus—like, well, eating. Sounds simple, until you’re confronted with a piece of dehydrated, butterscotch-dipped bacon hung from a taut wire. This concoction is a signature dish at Alinea, one of the avant-garde restaurants that have put the city at the forefront of the so-called molecular gastronomy movement.

But Chicago is also still a haven for chowhounds in search of no-nonsense potato pierogis and sausage-stuffed deep-dish pizza. Luckily, it’s easy to offset any culinary excesses with walks through this architecturally rich (and shopper-friendly) town. Bring comfortable shoes and get ready to sample a slice of Chicago—the cutting-edge and the classic.

AN APERITIF
“Some cities have mountains. Some have beaches. We have architecture,” says Jason Neises of the Chicago Architecture Foundation. “Architecture is our thing.” If you’re looking for a knowledgeable guide to this legacy, sign up for one of the foundation’s docent-led tours. The Architecture River Cruise, a boat ride on the building-lined Chicago River, offers a superb overview (architecture.org; from $28). For a more intimate and specialized view, take the Historic Skyscrapers walking tour ($15), which helps explain Chicago’s role in creating the modern high-rise.

With all the architectural riches here, it’s easy to make your own tour. Start downtown at the Chicago Cultural Center (78 E. Washington St.). Listed on the National Register of Historic Places, this Beaux Arts library turned cultural clearinghouse is home to the indispensable Chicago Office of Tourism. Ask a security guard to point out the freshly restored Tiffany dome. Among other city highlights: Frank Lloyd Wright’s lobby updates on the Rookery (209 S. Lasalle St.); the elegant Reliance Building (1 W. Washington St.), an early steel-framed skyscraper clad in glass and terra-cotta; and the Carbide & Carbon Building (230 N. Michigan Ave.), an art deco jewel topped by a gold leaf–covered tower. Architecture buffs take note: The last two buildings now house great hotels.

MAGNIFICENT MILE
Continue north to reach the Magnificent Mile. As you cross the Michigan Avenue Bridge, take a moment to look down the Chicago River and spot such landmarks as the corncob-like Marina Towers and the ornate Wrigley Building.

Past the gothic Tribune Tower, Michigan Avenue is all about shopping. (The district includes four malls and more than 460 stores.) Between credit-card swipes, track your progress by means of the John Hancock Building. Though shorter than the Lego-like Sears Tower, this matte-black skyscraper wins points for its criss-cross braces and a vertigo-inducing taper as it rockets skyward 100 stories.

At Chestnut Street, head east towards Lake Michigan. You’ll find a pair of deceptively simple apartment towers designed by Mies van der Rohe at 860-880 North Lake Shore Drive. Unadorned and perfectly proportioned, the two somehow seem to be light enough to float above their recessed lobbies.

CHOICES, CHOICES, CHOICES
Eventually, shopping gives way to the posh residential area known as the Gold Coast. Though filled with unspectacular high-rise condos, the area retains a few historic mansions, especially along the leafy stretch of Astor Street just north of Division Street. Don’t miss the Charnley-Persky House (1365 N. Astor St.), designed by Louis Sullivan with help from a young Frank Lloyd Wright, who worked under Sullivan.

For art lovers, Chicago’s gallery scene sprawls over several districts. One easy place to start is in River North, where dozens of galleries are clustered along Franklin Avenue, just south of the Chicago Avenue stop on the Brown Line. This area is also home to one of the city’s best Italian beef sandwiches. (See restaurant listings under EAT.)

Shoppers should be sure to stop by the hip Wicker Park neighborhood. If it’s lunchtime when you exit at the Blue Line’s Division Street stop, you’ll need to decide between Mexican or Polish. (See EAT listings.) Once fueled, head west on Division Street; in a few blocks you’ll hit a string of locally owned boutiques. Penelope’s (No. 1913) stocks modern clothing brands like Hyden Yoo, A.P.C. and Sessùn. At Renegade Handmade (No. 1924) you can pick up an idiosyncratic souvenir made by one of the store’s small army of independent craftspeople. Stop next door for a lemon-lavender cookie sandwich at Milk & Honey (No. 1920). To see what’s on the fashion horizon, peruse the clothes at Habit, most of them by emerging designers (No. 1951).

FOOD WITH INSTRUCTIONS
In the last few years, Chicago has enjoyed a culinary revolution led by a gang of ambitious chefs who favor offbeat, quasi-scientific techniques—believe it or not, one has even employed a hand-held ion-particle gun in the kitchen. “Grant Achatz broke the mold, doing food that came with instructions,” says Penny Pollack, the dining editor at Chicago magazine. “That really paved the way. Chicago became a hotbed of creativity and Chicagoans embraced it. We didn’t pause for a second.”

Like the groundbreaking Catalan chef Ferran Adrià, the members of this culinary vanguard want to break food down to its most basic level so that they can reassemble it in amazing, shocking and—if all goes as planned—tasty ways. Here are some of the key practitioners.

CURTAIN UP 

At Alinea, a signless 20-table restaurant in Lincoln Park, you’ll be both surprised and delighted even before you sit down. (No, we won’t spoil the fun by telling you how.) Since its opening in 2005, chef Grant Achatz has earned national acclaim for his exacting cooking— the kitchen favors tweezers over tongs—and theatrical presentations. Whether it’s wild aromatics (one dish on the autumn menu incorporated the subtle smell of burning leaves) or custom-made tableware that requires bobbing for your bite, it’s safe to say that a meal here will, at some point, take you out of your dining comfort zone. But while you try to get your bearings, Achatz wins you over with his playful, flavor-packed dishes. Forget about the culinary alchemy and just smile.

As if the food wasn’t good enough, Achatz’s recent (and successful) battle with tongue cancer—even Shakespeare would blanch at such metaphorically rich stuff—has added a compelling story line. If a recent meal here is any example, his legacy should remain centered on the restaurant, which rises above any particular culinary style. Expect to spend three to five hours and drop a staggering $500-plus for two if you go for wine.

LOW-KEY, HIGH FLAVOR 

The restaurant named Schwa, located across from a tire-rim shop and looking permanently shuttered, is a far cry from Alinea. This small Wicker Park spot seems less magic carpet ride and more dinner party-cum-chef workshop. As at its molecular brethren, plates are bedecked with foam, and meat is cooked sous vide (in a vacuum). But chef/owner Michael Carlson’s nine-course prix fixe menu (a relative bargain at $110) seems more intensely focused on flavors. A rabbit-leg confit with peaches and wheatgrass somehow melded together wonderfully on the palate. On a recent visit, the two most challenging dishes (pickled beef tongue with fig, and a pad thai that replaced noodles with marinated jellyfish) were actually among the highlights.

Carlson and his three kitchen compatriots all act as servers and have been known to encourage wine-swapping among tables. (You bring your own wine; a crisp white and a light-bodied red are recommended.) With no formal reservation process, it’s notoriously tough to nab one of the 13 tables. But if you put in the effort (call and call again), you will have a fun, fun night.

UMMM... NAH 

Those last two restaurants make it seem easy to pull off a culinary high-wire act, but that’s not always the case. A recent visit to the much-lauded Moto was disappointing. Despite some memorable touches—such as spreading crème fraiche across Moto’s trademark edible menu—it all felt a little forced. Flavors take a backseat to novelty and innovation. Moto’s more casual à la carte offshoot, Otom, could offer diners an affordable way to savor the “molecular revolution.” But the best courses during a recent visit—a duck entrée and a delicious BLT appetizer—hewed closer to tradition than to any sort of buzzworthy deconstruction of culinary traditions.

END AT THE BEAN
Wind down your visit with a walk though Millennium Park, the most obvious symbol of the new Chicago. When it opened in 2004, this bold collection of art and architecture transformed a dreary lakefront parking lot into a hip new doorstep to the city. There’s a blockbuster bandshell designed by Frank Gehry, but the star here is the “Bean,” a legume-shaped sculpture (the real name is Cloud Gate) by Anish Kapoor that sits just off Michigan Avenue. Its curvy, stainless steel hull offers funhouselike reflections of surrounding skyscrapers and passersby.

The park’s Crown Fountain also enchants visitors by involving them. Kids can’t help but splash around the quarter-inch-deep pool between the glass-brick towers. Others stand transfixed by the glowing images of faces (Chicagoans all) projected on video screens embedded in the towers. Wait around to see those friendly faces blowing water onto the giggling kids below. The modern Lurie Garden and Gehry’s serpentine footbridge to the lakefront are also worth checking out. All these strongly conceived but disparate contributions make Millennium Park feel a bit disjointed. But it leaves you feeling excited, just like Chicago itself, with its deep-dish lunches and Alinea evenings.

EAT

*Prices cover a meal for two, not including drinks, tax or tip.

STAY

RCI-AFFILIATED RESORTS IN AND AROUND CHICAGO INCLUDE:

For more information, visit RCI.com or call
Weeks: 800-338-7777
Points: 877-968-7476

NON-RCI-AFFILIATED HOTELS: