Chicago may be known for its cold winters and lakefront chill, but locals know that the city's endearing "Windy City" moniker could apply to the notorious political corruption and wind-filled policymakers of the city's past. And while Chicago's location, on the western bank of Lake Michigan, does indeed receive its share of gusts throughout the year, the arrival of fall puts the city in a fine mood. The tourist droves seem to clear out after Labor Day, leaving a town with hotel vacancies and reduced rates, more-easily booked restaurants, and no shortage of indoor activities.
Learning the City
Chicago's topography and terminology is complex enough to require a quick lesson. "The Loop" is the city's downtown, named for the circumnavigation of the area by commuter and subway (the "L," for elevated) train tracks. Look on any map, and you'll see the train lines make a distinct loop around the central business district.
The Chicago River—famously redirected by engineers to flow away from Lake Michigan for waste management reasons—divides The Loop from the Northside, which includes a host of other neighborhoods. There's River North, named for its location just north of the river. To the northeast is Streeterville, an area of high-rise condominium and apartment buildings on the lakefront. North of Streeterville is the Gold Coast, where you'll find Astor Street's stately homes of the late 1800's and some of Chicago's most desirable residences.
To the northwest, Wicker Park and Bucktown are the alternative "indie" neighborhoods where recent gentrification has pushed the artist population even farther west. And finally to the far north, Lincoln Park and Lakeview consist of intermixed homes, stores, and restaurants.
Where to Stay
Travelers flock to Michigan Avenue, home to many hotel fronts with direct access to the shopping district known as The Magnificent Mile, but two intriguing options lie just off the busy thoroughfare. The newly renovated Hotel Cass (640 North Wabash Avenue, 312-787-4030, casshotel.com) just re-opened in September, and this boutique hotel may prove a less expensive option with the same conveniences of neighboring inns.
If cost is not a concern, the Peninsula Hotel (108 E. Superior Street, 312-337-2888, chicago.peninsula.com) is renowned for its superior service and celebrity status (it has hosted the likes of Jennifer Aniston and Angelina Jolie). Just off Michigan Avenue, Conde Nast Traveler named the 6-year-old luxury hotel's spa the top urban spa in North America last year. Ask about packages, including meals at the Peninsula's adjacent Peirrot gourmet cafe.
If you don't care for a view of Pizzeria Uno and Saks Fifth Avenue, or simply wish to avoid the bustle of the main hotel district and branch out into one of Chicago's other neighborhoods, consider Ray's Bucktown B&B (2144 N. Leavitt Street, 773-384-3245, raysbucktownbandb.com). In the heart of Bucktown's quiet residential streets, Ray's is a 15-minute drive from the Loop, and it can be reached via the Blue Line (it's a short walk from the station). Ray will kindly offer you a ride to the L, a goat cheese omelet, herbs for your omelet that he picked from his backyard garden, and a soak in the steam room. Ray's doesn't offer the Chicago skyscraper experience, but the place gives you a taste of how Chicagoans live.
Where to Eat
Chicago knows food, and Chicagoans know that every day should ideally start with brunch. For Saturday and Sunday fare, your best bet is to head down to the South Loop's Orange (75 W. Harrison Street, 312-447-1000) and create your own fresh squeezed juice concoction by selecting from a sushi-style checklist (grapefruit-cantaloupe-pineapple, anyone?). Speaking of sushi, Orange's "frushi" offers the fruit version of the Japanese staple with rolls made from sweet, sticky rice and fresh fruit (and chocolate sauce in place of soy). For the less fruity at heart, try the weekly pancake flight—four themed mini stacks with toppings such as pulled pork or Gummy Bears.
Another dessert-for-breakfast haven, Wicker Park's Bongo Room (1470 N. Milwaukee Avenue, 773-489-0690) specializes in tall, fluffy stacks of pancakes covered in toppings like chocolate shavings and crème anglaise. There are also steaming strawberry-rhubarb-doused waffles with a scoop of vanilla gelato on top; traditional day-starters include giant breakfast burritos and design-your-own omelets.
One sure way to identify yourself as a tourist in Chicago: Order your hot dog with ketchup. Chicago's famous institution Portillo's (100 W. Ontario Street, 312-587-8910) hasn't spent more than 40 years perfecting its hot dog to serve it without adequate toppings. At Portillo's, "everything" means everything: mustard, relish, onions, tomatoes, pickle and hot peppers—and that's the way you'll find it across the city. At $2.09 a pop, it's not a bad meal (and this big dog is a meal).
But the cornerstone of Chicago dining is its deep-dish pizza. The intersection of Ohio Street and Wabash Avenue is the wellspring for Chicago's adaptation of cheesy flatbread, and home to the original Pizzeria Uno (29 E. Ohio Street, 312-321-1000, unos.com)—its Number Two outpost, Pizzeria Due, is across the street.
While Uno lays claim to the oldest deep-dish pizzeria in the city, Lou Malnati's (439 N. Wells Street, 312-828-9800, loumalnatis.com) own take on the doughy delicacy, is one that many locals say they prefer. But be prepared to wait for your manna: Chicago-style crust is no quick fix. Properly done, the pie is made from dough, on the spot, unlike many East Coast locations where crusts are frozen and ready to go. Like most things in the Midwest, deep dish takes a while.
The culinary scene in Chicago has not only conquered the basics; the city is awash with foodie destinations. Two-decade-old Charlie Trotter's (816 W. Armitage Avenue, 773-248-6228, charlietrotters.com) is the creation of chef/owner Charlie Trotter, who produces three daily "degustation" menus with numerous courses served in a planned progression. Grant Achatz also presents a daily tasting menu at his Northside Alinea (1723 N. Halsted Street, alinea-restaurant.com, 312-867-0110). Courses are each based on one key ingredient (say artichoke, guava, or bison) and come in 12- and 24-course successions. Needless to say, reservations are required.
Chicago is also a beef-eater's paradise. Downtown's Gold Coast district is home to the original Morton's Steakhouse (1050 N. State Street, 312-266-4820, mortons.com) and Gibson's Steakhouse (1028 N. Rush Street, 312-266-8999, gibsonssteakhouse.com) two of the many steakhouses where Chicagoans tuck in for aged Midwestern beef.
What to See and Do
Chicago is known for its architecture almost as much as its food. The oldest still-standing skyscraper in town is The Rookery, built in 1885, at a whopping 10 stories. Slightly grander in scale, Chicago is also home to the tallest building in the Western Hemisphere (the Sears Tower, at 113 floors). However high you're willing to go, Chicago offers a wide array of historic buildings and breathtaking designs. The best views of Second City can be found from the 103rd story Skydeck of the Sears Tower (233 S. Wacker Drive, 312-875-9447, theskydeck.com) or from the 94th floor of the Hancock Tower (875 N. Michigan Avenue, 312-751-3681, hancock-observatory.com) northeast of the Loop. Stop by the Hancock's Signature Room on the 95th floor for a quick bite and an 80-mile view.
Visitors will recognize the iconic Marina City (300 N. State Street) as the giant "corncob" buildings on the Chicago River, and the immense, looming Merchandise Mart (Merchandise Plaza) from films and photos; once, they were the largest concrete and largest overall buildings, respectively, in the world. And they're accompanied by a host of other architectural wonders in the downtown area including the AMA building (State Street and Grand Avenue) and the Wrigley Building (400 N. Michigan Avenue).
Chicago's contributions to the American music scene are also storied and crucial; today, live blues can be found within walking distance of most downtown hotels. In River North, Blue Chicago (two locations, 736 N. Clark Street, 312-642-6261 and 536 N. Clark Street, 312-661-0100, bluechicago.com) features nightly blues bands Monday through Saturday. Farther north, find B.L.U.E.S. (2519 N. Halsted Street, chicagobluesbar.com) where local performers and out-of-towners set up shop every day of the week.
Members of Chicago's theater scene will tell you it doesn't try to be New York—and that's why it's been so successful. It offers its own series of unique venues while serving as a major stop for touring shows. Wicked plays at the Ford Center for the Performing Arts (151 W. Randolph Street, Chicago, 312-902-1400) through January 2008, and The Chicago Theatre (175 N. State Street, 312-462-6363, thechicagotheatre.com) opens its doors to Kathy Griffin on October 20.
What to Do
If you've spent all your time eating and sightseeing and only have time for one museum in Chicago, make it the Art Institute (111 S. Michigan Avenue, artic.edu). Just look for the immense building with huge bronze lion sculptures adorning the main entrance, just south of the new and still-popular Millennium Park.
The Institute's main collection includes painted highlights such as Edward Hopper's oil Nighthawks and Grant Wood's American Gothic, as well as works by Georgia O'Keefe, Juan Gris, Paul Klee, Henri Matisse, Pablo Picasso, and others. Another must-see includes the Thorne collection of miniatures, including 68 rooms built to the scale of one inch to one foot, creating a tour through European and American interior furniture and design. Additionally, through mid-October, visitors can peruse an exhibition of Lorenzo Ghiberti's famous bronze cast door panels from Florence.
And if you have time for one more museum, make it the Field Museum (1400 S. Lake Shore Drive, 312-922-9410, fieldmuseum.org). With a current focus on evolution in "Darwin," a traveling exhibition exploring the life and work of the natural selection theorist (through January 1), the museum also introduces "Sue," the largest intact Tyrannosaurus Rex skeleton in the world (see her 600-pound skull on the second floor of the museum). Adjacent to the Chicago Bears' stomping grounds, Soldier Field, the century-old Field Museum also includes the Shedd Aquarium and Adler Planetarium on its campus.
Where to Shop
They don't call it The Magnificent Mile for nothing. The famous stretch of retail along Michigan Avenue runs parallel to Lake Michigan, and is one of the nation's legendary shopping districts.
This section of Michigan Avenue—beginning where Water Tower Place sits at the base of Chicago's second-tallest building (the Hancock) and heading south to the Chicago River—is home to malls anchored by upscale department stores such as Nordstrom and Bloomingdales, a four-story Crate & Barrel, off-price Filene's Basement, and another 400 retailers. It's entirely possible to spend your entire vacation here, whether you plan to or not.
Adjacent streets (Walton and Oak) lead west from Michigan to boutiques and shops off the beaten path, ultimately leading to State Street. Head a half-mile south, just past the river, to find the former Marshall Field's building (now Macy's), once home to one of the largest department stores in the world.
For custom handbag creations, try the original 1154 Lill Studio (904 W. Armitage Avenue, 773-477-5455, 1154lill.com). The retail studio, which was first opened in 2001 by Jennifer Velarde, and has since expanded to locations in Boston and Kansas City, offers amateur handbag designers a boutique filled with hundreds of fabrics and more than 25 original bag styles to choose from. Customers select the fabrics and design and in three weeks, voila!, their custom handbags are shipped. Stylists are on staff to gently talk you out of any potential color combination faux pas, and to help assist with the painstaking decisions (wooden handle or cloth?). For those who'd rather not do it themselves, there are ready-made bags for purchase in the store.
Just a few doors down, Lori's (824 W. Armitage Street, 773-281-5655, lorisshoes.com), "the sole of Chicago," has a shoe to match every bag—custom or otherwise. Hordes of locals flood Lori's during the weekend days in search of the perfect flats, pumps, and wedges, and more often than not they walk out with a pair (or two).
Across town in the West side's Wicker Park neighborhood, hipsters in skinny jeans scour the racks at dozens of indie shops for vintage gear, antiques, and local creations. Take Damen Avenue north from Wicker Park and find recently gentrified Bucktown with its dozens of boutiques, restaurants, and artsy flair.
Making the Scene
The departure of the tourist throngs—and the spectre of winter's approach—make fall a popular social season in Chicago. After a weekend dinner in The Gold Coast, Chicagoans head to newly relocated Pops For Champagne (601 N. State Street, 312-266-POPS, popsforchampagne.com) for a taste of one of Pops' more than 125 champagnes or signature cocktails followed by jazz in the downstairs space, designed to resemble a European live music club. Across the street at Quartino (626 N. State Street, 312-698-5000, quartinochicago.com), the beautiful people gather around the all-Italian wine bar; the vino comes in full, half, or "quartino" carafes alongside tapas-portions: sausage orecchiette, design-your-own antipasti, and other tiny Italian staples topped off with biscotti dipped in chocolate fondue.
Head west to chic new loft-style restaurants and lounges in Chicago's meatpacking or "stockyards" neighborhood for Latin-inspired cuisine and fruit-flavored mojitos among bright, citrus-colored décor and massive decorative fixtures at Carnivale (702 W. Fulton Market, 312-850-5005, carnivalechicago.com).
Getting There, and Getting Around
About 700 miles (or an 11-hour drive) from Baltimore, Chicago is best reached by way of its two major airports: O'Hare Airport, 20 miles due west of the city, serves direct flights from BWI on United (from $118), American (from $292), and US Airways (from $333); Midway Airport, the smaller of the two, can be reached direct via Southwest (starting at $180 round trip) from BWI.
Chicago's elevated "L" trains run to both airports: From O'Hare, take the Blue Line train to the Loop; from Midway, board an Orange Line train to the Loop. "L" tickets can be purchased with cash for $1.75 per trip or $5 for a full day.
There are plenty of taxis that will run the meter to downtown from either airport; the rate is around $30 from Midway and a few dollars more from O'Hare. Likewise, taxis in the city are abundant and inexpensive.
One important travel tip: the Chicago Marathon is Sunday, October 7, which means that swaths of downtown will be inaccessible to vehicle traffic.