Chicago

Steely skyscrapers, top chefs, rocking festivals – the Windy City will blow you away with its low-key cultured awesomeness.

Art & Architecture

It's hard to know what to gawk at first. High-flying architecture is everywhere, from the stratospheric, glass-floored Willis Tower to Frank Gehry's swooping silver Pritzker Pavilion to Frank Lloyd Wright's stained-glass Robie House. Whimsical public art studs the streets; you might be walking along and wham, there's an abstract Picasso statue that's not only cool to look at, but you're allowed to go right up and climb on it. For art museums, take your pick: impressionist masterpieces at the massive Art Institute, psychedelic paintings at the midsized Museum of Mexican Art or outsider drawings at the small Intuit gallery.

Chowhounds' Delight

Loosen your belt – you've got a lot of eating to do. On the menu: peanut-butter-and-banana-topped waffles for breakfast (at Stephanie Izard's Little Goat), pork-shoulder posole and garlicky yucca enchiladas for lunch (at Dove's Luncheonette) and fine dining on foraged foods for dinner (at Iliana Regan's Elizabeth). You can also chow down on a superb range of global eats from Vietnamese pho to Mexican carnitas, Polish pierogi and Macanese fat rice. Still hungry? Order a late-night deep-dish pizza or seek out a hot and spicy Italian beef sandwich at a local fast-food joint.

Sports Fanatics

Chicago is a maniacal sports town, with a pro team for every season (two teams, in baseball's case). Watching a game is a local rite of passage, whether you slather on the blue-and-orange body paint for a Bears football game, join the raucous baseball crowd in Wrigley Field's bleachers, or plop down on a bar stool at the neighborhood tavern for whatever match is on TV. Count on making lots of spirited new friends. Should the excitement rub off and inspire you to get active yourself, the city's 26 beaches and 580 parks offer a huge array of play options.

Rollicking Festivals

Chicago knows how to rock a festival. Between March and September it throws around 200 shindigs. The specialty is music. Blues Fest brings half a million people to Millennium Park to hear guitar notes slide and bass lines roll, all for free. During the four-day Lollapalooza megaparty, rock bands thrash while the audience dances in an arm-flailing frenzy. Smaller, barbecue-scented street fests take place in the neighborhoods each weekend – though some rival downtown for star power on their stages (oh, hey, Olivia Newton-John at Northalsted Market Days).

Must see in
Chicago

  • Art Institute of Chicago

    The second-largest art museum in the country, the Art Institute houses a treasure trove from around the globe. The collection of impressionist and postimpressionist paintings is second only to those in France, and the number of surrealist works is tremendous. Wander the endless marble and glass corridors, and rooms stuffed with Japanese prints, Grecian urns, suits of armor, Grant Wood's American Gothic, Edward Hopper's Nighthawks and one very big, dotted Seurat. The Modern Wing dazzles with Picassos and Mirós.

  • Millennium Park

    The playful heart of the city, Millennium Park shines with whimsical public art. Go ahead, walk under Anish Kapoor's Cloud Gate – aka 'the Bean' – and touch its silvery smoothness. Let the human gargoyles of Jaume Plensa’s Crown Fountain gush water on you to cool down in summer. Unfurl a blanket by Frank Gehry's swooping silver band shell as the sun dips, wine corks pop and gorgeous music fills the twilight air. Or try to find the secret garden abloom with prairie flowers and a wee, gurgling river.

  • Wrigley Field

    A tangible sense of history comes alive at this 100-plus-year-old baseball park, thanks to the hand-turned scoreboard, iconic neon entrance sign, legendary curses and time-honored traditions that infuse games played here. Shoveling down hot dogs and drinking beer in the raucous bleachers makes for an unforgettable afternoon. The area around the stadium is like a big street festival on game days: young people party in alfresco bars, kids lick ice-cream cones, and die-hard fans occupy stools in age-old, sticky-floored taverns.

  • Sky-High Views

    For superlative seekers, Willis Tower is it: the city's tallest building (and one of the world's loftiest). Breathe deeply during the ear-popping, 70-second elevator ride to the 103rd-floor Skydeck, then stride to one of the glass-enclosed ledges that jut out in midair. Look down some 1400ft. Crikey. The lakeside 875 N Michigan Ave building (formerly known as the Hancock Center) also rises high in the sky. Ascend to the 96th-floor Signature Lounge, order a cocktail and watch the city sparkle around you. It's especially lovely at night.

  • Blues & Rock

    In Chicago no genre is as iconic as the blues – the electric blues, to be exact. When Muddy Waters and friends plugged in their amps c 1950, guitar grooves reached new decibel levels. Hear it in clubs around town, such as Buddy Guy's Legends, where the icon himself still takes the stage, or Rosa's Lounge, where it's a bit more down and dirty. The blues paved the way for rock and roll, so no surprise cool little clubs hosting edgy indie bands slouch on many a street corner.

  • Comedy & Theater

    A group of jokesters began performing intentionally unstructured skits in a Chicago bar a half century ago, and voilà – improv comedy was born. Second City still nurtures the best in the biz, though several other improv theaters also work from booze-fueled suggestions that the audience hollers up. Among the city's 200 theaters are powerhouse drama troupes such as Hollywood-star-laden Steppenwolf, and heaps of fringey, provocative 'off-Loop' companies, such as the Neo-Futurist Theater (which bases its admission cost on a dice roll).

  • Navy Pier

    Stretching away from the skyline and into the blue of Lake Michigan, half-mile-long Navy Pier is one of Chicago’s most visited attractions. Its charms revolve around the cool breezes and sweet views, especially from the stomach-turning, 196ft Ferris wheel. High-tech rides, splash fountains, big boats and greasy snacks blow the minds of young ones. Live music, Shakespearean theater and whopping fireworks displays entertain everyone else. A smart renovation has added public plazas, performance spaces, art installations and free cultural programming.

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