Reveling in Chicago
Chicago is impressive. It’s a sweeping city that wakes up early and stays alive well into the witching hour. Renowned for its classic American appeal, this urban hub is a wealth of culture in every shade and style — and has been for decades. This fall, go beyond the basics (though, we don’t suggest you skip the Schlitz and the deep-dish) to experience all manner of diversions tucked into Chicago’s neighborhoods. Nobody accuses this city of not having enough fun or taking itself too seriously. So go out on a limb, befriend your neighbors, and try something new. If you end up at one of these spots, you’re in for a treat.
There’s a solid history of great music in Chicago that starts with the blues, and has led to the evolution of an acclaimed hip hop scene — Kanye, Common, and Chance to start — plus some serious rock, punk, and indie clout — Smashing Pumpkins anybody?
If you’re looking for a taste of expert guitar tickling, get a table at Buddy Guy’s Legends (700 S. Wabash Ave) where blues sets come with dinner every night. Don’t miss The Green Mill (4802 N. Broadway Ave), known as the oldest jazz bar in the nation. It boasts jazz from across the genre, reasonably priced drinks, plus a gorgeous Renaissance style interior that will make you feel grand and important.
To get in on local acts, indie bands, or hopping dance parties, try The Whistler (2421 N. Milwaukee Ave), Subterranean (2011 W. North Ave), and the Empty Bottle (1035 N. Western Ave). The new Thalia Hall (1807 S. Allport St) showcases those so-hot-right-now bands that you gotta see to be anybody.
Extra: Should you happen to spot a crowd on the sidewalk watching furry puppets sing, dance, and emote inside of a vividly painted box on wheels, you’ve been lucky enough to run into the celebrated Puppet Bike.
Chicago is a town that doesn’t shy away from a drink. Whatever neighborhood you end up in, there’s most certainly a great bar around the corner just waiting to make your day. However, there also are some adult beverage destinations that merit a journey.
For those who savor the agony of picking the right craft beer for each exact moment, the Map Room (1949 N. Hoyne Ave), the Hopleaf (5148 N. Clark St), and Twisted Spoke (501 N. Ogden Ave) offer vast selections of beer in an atmosphere that supports the actual tasting of beer. The Hopleaf (whose upstairs tends to be less chaotic) also features a food menu suited for the palate of the discerning beer drinker, and the Twisted Spoke, which also offers a solid selection of bourbon, invites visitors to enjoy the deck patio. Beer lovers are also advised to make a stop in at Half Acre Lincoln Brewery (4257 N. Lincoln Ave), where you can get a brewery tour that offers tastes and insights on their latest brews.
Should beer not do it for you, Chicago is also home to some incredible cocktail bars that manage to finagle a baffling number of life experiences into a drink. Band of Bohemia (4710 N. Ravenswood Ave), created by some of the masterminds in the city’s fine dining scene, has a playful cocktail menu plus an always-interesting, reliably good wine list that includes sherry.
Scofflaw (3201 W. Armitage Ave), known for its gin cocktails, and The Barrelhouse Flat (2624 N. Lincoln Ave) serve up excellent takes on classic, old-fashioned cocktails. Finally, margarita lovers can take their pick at Del Toro (2133 S. Halsted St), a tequila bar with a gazillion kinds of margs, and delicious tacos that will keep you there longer than you planned.
Extra: If you’re a history buff who prefers to explore yesteryear with a drink in hand, Chicago Detours offers an Historic Chicago Walking Bar Tour that’ll fortify you with knowledge and drinks!
Dining in Chicago works on a lot of levels. For your casual munchies, there are taco shops all over town, a healthy debate over the greatest Chicago hot dogs, and of course, the proud legendary deep-dish joints. Then there are the very upscale Alinea (1723 N. Halsted St), Acadia (1639 S. Wabash Ave), and 42 Grams (4662 N. Broadway St) restaurants with inspired dishes featuring ingredients in unrecognizable forms.
For eating pleasures somewhere in between, Logan Square is lit up with a number of crowd-pleasing spots, including Lula Cafe (2537 N. Kedzie Ave), a brunch favorite, and Longman & Eagle (2567 N. Kedzie Ave), a well-crafted whole animal and whiskey paradise.
For bold new takes on Asian flavors, check out the bomb chicken wings at Crisp (2940 N. Broadway), marinate in the Macanese offerings at Fat Rice (2957 W. Diversey Ave), and relish the elegant Korean-American flavors at Parachute (3500 N. Elston Ave).
Finally, don’t miss Devon St., which hosts a throng of Indian restaurants – really Indian everything. Opt for the spicer, tangier, and mostly vegetarian South Indian favorites, like dosas and vada, at Mysore Woodlands (2548 W. Devon Ave).
Chicago’s Museum Campus sets a very high bar for museums in the city, and is a must-see for first-timers. The Field Museum (1400 S. Lake Shore Dr) and the Shedd Aquarium (1200 S. Lake Shore Dr) are heaven for those curious about science, animals, and nature. Additionally, the Museum of Science and Industry (5700 S. Lake Shore Dr), while it requires a trip further south, gets kids and adults equally whipped up about robots, submarines, and storms.
If art is your vibe, the Art Institute of Chicago (159 E. Monroe St), with its sleek, Renzo Piano-designed Modern Wing, has one of the largest collections in the world. But don’t miss the Museum of Contemporary Art (220 E. Chicago Ave), where you can always find a throught-provoking exhibit, and the University of Chicago’s Smart Museum of Art (5550 S. Greenwood Ave), where the art often engages more than just your eyes, and is free everyday.
Getting to know the history and the people that compose a city give it an extra layer of richness. So check out the Chicago History Museum (1601 N. Clark St), to learn all about the historic fire and for photo ops on vintage train cars. Also stop in at The DuSable Museum of African American History (740 E. 56th Pl), which is small, but packed with powerful Black history, and the National Museum of Mexican Art (1852 W. 19th St) with a huge collection of Mexican art, and an array of awesome concerts, festivals, and art lessons.
The famed comedy scene in Chicago doesn’t disappoint. The Neofuturists (5153 N. Ashland Ave) pull off crazy improv stunts, Zanies Comedy Club (1548 N. Wells) gives you a dose of straight-up stand-up, and the powerhouses, Second City and iO Chicago (1501 N. Kingsbury St), keep the laughs rolling.
When it starts to get chilly out, get cozy in a movie theater. For cinematic experiences that go beyond the ordinary buttered popcorn, check out the $5 flicks at the The Vic’s Brew & View (3145 N. Sheffield Ave) and the curated film selection at The Musicbox (3733 N. Southport Ave).
Sports fandom is a serious and impassioned pastime in Chicago, performed with enough regalia and heart to rival any theatrical production. With hockey and basketball just revving up, check out the Blackhawks and Bulls schedules to get in on some pre-season action.