Steely skycrapers, top chefs, rocking festivals – the Windy City will blow you away with its low-key cultured awesomeness
Why I Love Chicago
I've lived in the city for 25 years, and I never get bored. There's something groovy going on any night of the week. Like tonight: should I see the Grant Park Orchestra playing Shostakovich's 5th Symphony in Millennium Park, or a guitar-drum duo called Earring at Empty Bottle? I love that Tibetan dumplings, Mexican carnitas and crème brûlée donuts are all equally, easily accessible from local eateries. I love how total strangers sitting next to each other in a bar watching a Blackhawks game become high-fiving pals by evening's end. Chicago really is my kind of town.
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 Pritzer Pavilion to Frank Lloyd Wright's stained glass Robie House. Whimsical public art studs the streets. So you're walking along and wham, there's an abstract Picasso statue that's not only cool to look at, 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 mid-sized Museum of Mexican Art or outsider drawings at the small Intuit gallery.
Loosen the 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), a fig and goat cheese slathered elk sausage for lunch (at Hot Doug's hot dog shop), and 20 courses of centrifuged, encapsulated molecular gastronomy for dinner (at Grant Achatz's Alinea).
You can also chow a superb range of ethnic eats from Vietnamese pho to Mexican carnitas, Polish pierogi and Swedish almond tarts. Still hungry? Order a late-night deep-dish pizza.
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 24 beaches and 580 parks offer a huge array of play.
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 Grant Park to hear guitar notes slide and bass lines roll, all for free. During Lollapalooza's three-day mega-party, 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).
Best places to stay in Chicago
Chicago city guide
Steely skyscrapers, top chefs, rocking festivals - the Windy City will blow you away with its low-key cultured awesomeness.
Chicago's top 10 peculiar (and free) museums
Several of the Windy City's big-name museums recently raised their ticket prices. Puh-leez...
Best theatre & entertainment in Chicago
Best places to eat in Chicago
Chicago - Plan your trip (Chapter)
Your journey to Chicago starts here. You'll find the tools to plan your adventure: where to go, how much to budget, plus info on Chicago's nightlife and entertainment scenes.
Chicago’s best homegrown junk food
Chicago sits on the shores of Lake Michigan, vibrant and glimmering, the jewel of the Midwest. Known the world over for its gorgeous architecture, impressive museums, legendary sports teams, barely tolerable winters, and cutting-edge cuisine, The Windy City is also home to some of the best junk food this nation has to offer...
Chicago - The Loop (Chapter)
The Loop is Chicago's center of action, named for the elevated train tracks that lasso its streets. The Art Institute, Willis Tower, Theater District and Millennium Park are top draws among the skyscrapers.
Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions. The Chicago CityPASS ensures you'll get the most out of your vacation - yet it is so compact it will fit into your back pocket.
Chicago City Hop-on Hop-off Tour
See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off or get on at any other regular stop on the route.
Chicago: a starter guide to the Windy City
Welcome to the Windy City! While Chicago’s nickname is courtesy of the blustery weather, it’s the heights that it should be known for. Home to towering skyscrapers and sky-high spending sprees, this town was built to exceed expectations. Here you’ll find the essentials for raising the bar on your own trip to Chi-town...
Chicago - Andersonville & Uptown (Chapter)
Wrigley Field, both cursed and hallowed, draws baseball pilgrims. The bar-filled neighborhood around it parties hard and collides with the rainbow banners of Boystown, the nearby gay district. Kicky eateries and shops cater to the masses.