Introduction

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.

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.

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.

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).

By Karla Zimmerman, Writer

I've lived in Chicago for almost 30 years, and the skyline still kills me. Every time I take the train toward downtown it's like the buildings suddenly pop up and expand storybook-style. I never get bored here; there's something groovy happening nightly. Like tonight: should I listen to an Afrobeat ensemble playing at SummerDance, see free improv at the neighborhood dive bar, or watch a musical about the bubonic plague at a storefront theater? Mostly I love how total strangers watching a Cubs or Hawks game in a bar become high-fiving pals by evening's end.