The epicenter of Chicago is the Loop, the downtown business and commercial district. Just south of the Loop is the Museum Campus, a lakefront area that houses the Shedd Aquarium and other sights; meanwhile, just north lies the Magnificent Mile, a stretch of North Michigan Avenue dedicated to shopping, some of it upscale. Travel north of that, and you’re officially on the North Side, a conglomeration of neighborhoods that combine residential space with fantastic restaurants, historical sights and sport venues such as Wrigley Field. If you want to get off the beaten path, venture south of Roosevelt Road to the South Side, or west of the Loop to the West Side, both of which offer fascinating sights that most visitors never come across. Note: While plenty of South and West Side neighborhoods are safe to visit, others can be dangerous, so do your homework before setting out. You don’t want your Chicago vacation to turn sour.
If you’re a first-timer in Chicago, you’ll probably spend at least a day exploring downtown—more if you add a museum or two. In Chicago, “downtown” is a loose term that can refer to the Loop (bounded by the Chicago River, Lake Michigan and Roosevelt Road) or to the areas adjacent to it. Those include: to the south, the Museum Campus, site of several major museums; to the north, the Magnificent Mile, a segment of North Michigan Avenue that houses major retailers and fancy-pants boutiques alike; and to the west, the West Loop, home of Oprah Winfrey’s Harpo Studios and a cluster of hip restaurants. In the Loop itself, attractions include Millennium Park, the Art Institute and the Willis Tower, which has lost its “Sears” moniker but not its status as the tallest building in the country. One nearby attraction is Navy Pier, a miniature amusement park and shopping area. You’ll have to decide if the (admittedly cool) view from the top of its Ferris wheel is worth braving sticky-faced kiddies and chain restaurants.
The third-largest Chinese community in the United States, Chicago’s Chinatown is kitschy but still worth a trip, especially for foodies. The Phoenix restaurant here is widely regarded as offering Chicago’s best dim sum—basically a Chinese version of tapas, in which the wait staff pushes carts full of pork buns, shrimp dumplings and other delicacies from table to table, offering diners their wares. Get there as early as you can manage on a Saturday or Sunday to avoid the lines. Afterward, browse some of the small shops offering tea, souvenirs and hanfu (traditional Chinese clothing). You’ll find Chinatown just south and west of the Loop.
Another excellent escape-the-hordes outing, Pilsen is a largely working-class Mexican neighborhood with a burgeoning art scene and fantastic taquerías and bakeries. It’s especially fun to visit in October, when stores peddle sugar-skull candies and grinning skeleton figurines in celebration of the Latin American holiday Dia de los Muertos (Day of the Dead). Don’t miss the small but fascinating National Museum of Mexican Art—or the tres leches cake at Kristoffer’s Cafe and Bakery. Pilsen gets a touch dicey after dark, but exercise basic caution and you’ll be fine.
North of Lincoln Park, Lakeview is less a neighborhood unto itself than it is a conglomeration of several smaller neighborhoods, each with its own identity. Most visitors head to the one called Wrigleyville, to catch a Cubs game at Wrigley Field or just to drink at one of the many, many sports bars. Most LGBT visitors, on the other hand, head to Boystown, Chicago’s most prominent gay and lesbian area—you’ll know you’re there when you see the rainbow pylons. The nightlife here is lively and loud. And then there’s West Lakeview, worth visiting mainly for the Southport Corridor, a stretch of Southport Avenue between Belmont Avenue and Clark Street where you’ll find shopping, dining and the landmark Music Box Theatre, which still shows movies in its atmospheric 1920s-era auditorium.
Not to be confused with the more posh Lincoln Park, Lincoln Square is a down-to-earth enclave of quirky shops and mid-price restaurants. It’s the place to go when you’re sick of navigating crowds, and just want a laid-back day of shopping, strolling and noshing. This was originally a German neighborhood, a fact evident in spots like Gene’s Sausage Shop, the Chicago Brauhaus restaurant and the Merz Apothecary, which sells European personal care items. When you’re ready for a break, head to the small central plaza, grab a cup of coffee and a pastry from nearby Café Selmarie, sit on one of the outdoor benches and watch the world go by.
Hyde Park is its own world, an academic citadel incongruously plopped in the middle of the South Side. Anchored by the highly regarded University of Chicago, it’s a very walkable neighborhood, with a refreshing dearth of chain stores. On a sunny day, it’s pleasant to stroll around the university, gawk at its Gothic architecture and wonder if that scruffy fellow in the tweed jacket is one of the university’s many Nobel Prize winners. On a rainy day, hole up in one of the neighborhood’s plentiful bookshops, visit the Museum of Science and Industry or take a tour of the Frank Lloyd Wright-designed Robie House. The Obamas’ house is just outside Hyde Park, at 5046 S. Greenwood Ave., but you can’t get terribly close to it. Note: Despite the South Side’s reputation for violence, Hyde Park is a very safe neighborhood.
Lincoln Park, just a few minutes north of downtown, has a reputation for wealth. You might hear its residents dismissed as “Trixies” or “Chads”—local nicknames for someone who is affluent, spoiled and out of touch with life in the rest of the city. Well, Lincoln Parkers might be wealthy, but their neighborhood also has a wealth of attractions for visitors, including the Lincoln Park Zoo (which is, ahem, one of the last free zoos in the country). It’s also the home of the Chicago History Museum, one of the city’s best, and legendary theaters Second City and Steppenwolf. The shopping here consists mostly of quirky-but-pricey boutiques, and while there are plenty of places to eat, the best of them—like Charlie Trotter’s—will put a dent in your wallet.
Once one of Chicago’s swankiest neighborhoods, Uptown slid into decay in the 1950s, and has never recovered its former glory. But a mélange of historical attractions, music venues and cheap-but-tasty ethnic restaurants has kept it thriving amid the grit. This is not a place to walk around alone after dark, especially at the intersection of Broadway and Wilson avenues, but it’s perfectly safe during the day, or at night with a companion. A tour of Graceland Cemetery, where dozens of famous Chicagoans are buried (including railroad magnate George Pullman and Andrew McNally of Rand McNally fame) is a must. So is a trip to the Green Mill, a former speakeasy once frequented by Al Capone that’s now a highly respected jazz venue. Check out the area around the Argyle L stop for a slew of Vietnamese restaurants that are as authentic (and inexpensive) as they come.
Some say Wicker Park has jumped the gentrification shark, but, for the most part, this Near West Side neighborhood is still hipster central. (Just look for the ironic T-shirts and trucker hats.) This is the place to come for indie comics, used LPs, vintage clothing, dive bars and small but excellent music venues. It’s worth trekking to Wicker Park just for the Hideout, an alt-country/rock bar tucked away in an alley, and the Violet Hour, a very popular upscale speakeasy with legendary drinks.