Your Guide To Chicago
There are plenty of fun things to do in the windy city
Art
Beyond Chicago’s most revered museums, a kaleidoscope of public art can be found throughout the city, begging to be admired, questioned, interpreted and made Instagram-famous.
Sure, you could head to one of Chicago’s art museums to satisfy your artistic whimsy. Or you could simply stroll the city streets, where eye-popping public art poke through at almost every corner. More than 500 works of art are sprinkled across the city -- from the water-spitting faces of the Crown Fountain and the selfie-famous Cloud Gate (a.k.a. “The Bean”) at Millennium Park to the sublimely eerie 106 headless and armless iron sculptures of the Agora in Grant Park. As more businesses and schools hire graffiti artists, muralists and mosaic artists to transform the unremarkable into something memorable and meaningful, Chicago further transforms into a living art museum. For instance, Violet Hour, an upscale cocktail lounge in Wicker Park without a sign, features an ever-changing graffiti mural that hides its “secret door,” and several of the underpasses below Lake Shore Drive (accessible from the Lakefront Path) boast handmade mosaics and murals that tell the stories of its neighborhoods. One neighborhood worth strolling for the eye-catching vibrancy of its myriad of murals is Pilsen. Up and down 16th Street, you’ll spot colorful murals by revered local artists JC Rivera and Hebru Brantley, along with a growing collection by international street artists. From the Chicago River to Western Avenue, the walls of an old railroad embankment have been transformed into an evolving outdoor gallery of murals, as well. Of course, Chicago’s collection of art museums hold their own, and if you’re going to visit one, make it The Art Institute of Chicago. It’s a regal downtown fixture home to works by artists known worldwide by single names: Picasso, Monet, van Gogh, Chagall … the list goes on. While there, be sure to spend time in the Thorne Rooms, a beloved collection of pint-sized rooms detailing styles from the 13th century to the 1940s, built on a scale of one inch to one foot, right down to the miniscule textiles and carpets. (If you’re into Tiny houses, this takes that trend to an even teenier and curiously mesmerizing level.) Meander the Art Institute alongside art students, families, tourists and businessmen on break, as many step into the setting for a reprieve and to be inspired – the same could be set for spending time with Chicago’s abundance of public art, too.
Offbeat Chicago
The Windy City serves up the wonderfully weird and quirky, especially if you know where to look.
Oregon’s Portland doesn’t have a monopoly on “weird,” as its unofficial slogan might lead you to believe. Find the bizarre, the curious and the wacky alive and well in Chicago. Belly up to the bar early at Big Joe’s, where turtle racing has been a mainstay on Friday nights. Rooting for the fastest slow-moving animal on the track has never been so thrilling, especially when it involves cheap drinks in one of Chicago’s quintessential watering holes. To satisfy late-night hunger (perhaps after watching a few turtle races), head to the Weiner’s Circle for a Chicago style char-dog (no ketchup) and a side of verbal harassment from the famously sassy, profanity-loving cashiers who serve the after-hours crowd, many of whom come simply to participate in the fun tit-for-tat spectacle. (The char-dogs are great, by the way, as is the entertainment that typically ensues at this cash-only hot dog stand after midnight.) Forgo the popular museums for the bizarrely niche ones, such as the Leather Archives & Museum, a surprisingly serious preservation and education of leather, kink, BDSM and fetish lifestyles; the International Museum of Surgical Science, where macabre exhibits include preserved body parts and a vintage iron lung; or the Busy Beaver Button Museum, a small-but-mighty (and free!) museum boasting more than 9,000 historical pin-back buttons. As for tours, why not brag to friends about becoming a Chicago murder expert – the historical kind, of course – with Chicago Crime Tours, a luxury limo bus tour that highlights infamous Chicago crimes and serial killers, or the Untouchable Tours, a two-hour excursion led by costumed “wise guys” that travels to notorious sites of murder and mayhem from the Prohibition era, when Al Capone was the unofficial mayor of Chicago. Continuing with that theme, end your night at The Drifter, a 20s-era speakeasy in the basement of the legendary Green Mill Tavern, where drink menus are presented on tarot cards and magicians and burlesque dancers are among the nightly entertainment.
Shopping
Indulge in some retail therapy in Chicago’s most beloved shopping districts, where treasures that you didn’t know you needed await.
Considered by some to be the Holy Grail of shopping in Chicago is the famous Magnificent Mile, the northern section of Michigan Avenue that extends through the Gold Coast neighborhood. It’s a bustling window-shopping extravaganza where the people watching can be as much fun as the shopping. Situated between the Shops at Northbridge to the south and Water Tower Place mall to the north, both of which are home to hundreds of stores, sits the world’s largest Starbucks – a massive, three-story temple of caffeine to re-fuel your shopping. When you’re done with the Mag Mile scene, hop a Chicago water taxi, accessible on the southern end of the Magnificent Mile, for Chinatown to explore its eclectic array of shops, some of which are a jam-packed maze of treasures ranging from patterned tea sets to exotic candies to electronic lotus flowers to stacks of fake money -- something certain to fool and entertain folks back home. For a concentrated cluster of one-of-a-kind vintage shops and vinyl stores, the Wicker Park neighborhood is a must. Popular with artists, musicians and the modern indie set, the stretch of Milwaukee Avenue that runs through this neighborhood is where you’ll find mini music meccas such as Reckless Records, Shuga Records and the nearby Dusty Groove, along with some of the city’s coolest vintage apparel shops, such as Store B, Una Mae’s and Vintage Underground. For one of the fanciest – and liveliest – flea markets you’ll ever experience, check out the antiques, fashion, jewelry and global goods for sale at the Randolph Street Market. Held one weekend (Friday-Sunday) each month in Chicago's historic West Loop/Fulton Market district, it’s been named by USA Today as one of the “Top 10 Flea Markets in America.”
Sports
Cheer alongside (and trade barbs with) locals in this sports-obsessed town.
Chicago lives and dies by its beloved sports teams. If you thrive on game day adrenaline, this city could be your sports nirvana. It’s the home of Michael Jordan, who led the Chicago Bulls to six NBA Championships, and whose bronze in-flight statue is a popular selfie spot for fans. It’s the home to the Chicago Bears, a football team whose 1985 Super Bowl win is still very much a point of pride amongst fans who occasionally burst out into the classic rap “Super Bowl Shuffle.” It’s the home to a world-champion hockey team, the Blackhawks, and two baseball teams, the White Sox and the Cubs. If you can’t score tickets to a game, you’ll find excitement and camaraderie in neighborhood bars, where celebratory cheers (and groans) echo loudly on game days. Wrigleyville, the center of the Cubs universe, is a particularly colorful neighborhood, even when it’s not a game day. Belly up to the bar at popular spots like the Cubby Bear or Murphy’s Bleachers, or pay a little extra to snag a seat at one of the rooftop bleachers that peek over the outfield for a unique vantage point of games at historic Wrigley Field, the oldest park in the National League. For the South Side flavor, head to Reggies Chicago or Maria’s Packaged Goods and Community Bar and do a few shots of Malort (seriously, we dare you) with locals cheering on crosstown baseball rival, the White Sox. After working up an appetite of participating in Chicago’s frenzied sports enthusiasm, feast at these carnivore-friendly, sports-fan favorites: Ditka’s Restaurant, Harry Caray’s Italian Steakhouse or Michael Jordan’s Steakhouse.
