Let’s be honest, Chicago is a pretty big city, and the range of things to do, see, eat and experience is even bigger. From the cloud-scraping skyline to the sandy beaches to the diverse neighborhoods full of unique character, everywhere you look in the Windy City, you’ll find something to love.
What to See
Frank Lloyd Wright once said that modern architecture started in Chicago, and there’s no question that the skyline is a huge draw for architecture fans. Chicago has a building from almost every major architect, as well as other structural and artistic sights like the world’s largest collection of movable bridges, Frank Gehry’s concert pavillion, and the iconic “bean” (actual name: Cloud Gate). Join Chicago Line Cruises for one of their architectural or historic tours (with or without cocktails) and learn from the experts while you float on the Chicago River and enjoy complimentary cookies and Starbucks coffee.
For a dramatic view of the skyline from above (and a little bit of a thrill), go up to the 103rd floor of the Willis (née Sears) Tower, the second tallest building in the Western Hemisphere, and visit the Skydeck. Learn about the Tower and Chicago itself, through museum-quality exhibits, or stand out on the Ledge—glass boxes extending out from the building, 1,353 feet above the ground. Tip: for an extra-special experience, make a reservation for one of the Dining on the Ledge options, and enjoy some of Chicago’s best food in an exclusive, once-in-a-lifetime setting.
Frank Lloyd Wright may have said that modern architecture started in Chicago, but Wright himself also started his architecture career in Chicago. The easiest and most informative way to navigate the best of Wright’s Chicago is through the various tours given by the Frank Lloyd Wright Trust. Take advantage of the daylong Wright Around Chicago tours on Wednesdays, June through October, to visit four of Wright’s buildings: his home and studio, the iconic Robie House, the stunning downtown Rookery, and Unity Temple, his only surviving public building in the Prairie Style.
Chicago has been a shopping destination for more than a century, and with everything from the classic Michigan Avenue Magnificent Mile to independent neighborhood boutiques, you’re sure to find something in any budget and style that your heart desires. Head over to Wicker Park and spend some time browsing through the collection at one of Chicago’s best record stores, Reckless Records, or shop for new, vintage, and handmade treasures at modern-day general store Rudy’s Roundup. Also in the neighborhood is Quimby’s, an independent bookshop selling independently published and small-press books, comics, and zines. The zine collection is especially impressive, and a lot of their stock is on consignment, allowing unknown writers to find an audience and you to find things you won’t be able to find anywhere else.
What to Do
Chicago has been repeatedly named “Best Sports City” by Sporting News, and with good reason. Sports fans have their pick from seven pro teams, so whenever you visit, there’s bound to be a game going on. For a real vintage Chicago experience, go to a Cubs game at Wrigley Field, the second-oldest MLB stadium. Cubs fans are known for their enthusiasm and undying loyalty, so if the stadium is sold out, watch the game from one of the neighboring rooftops.
Chicago has a long history of organized crime, and was home to some of the most famous gangsters in the world—Al Capone and John Dillinger just to name two. Chicago’s original gangster tour from Untouchable Tours helps you experience prohibition-era Chicago with accurate accounts of the exploits of Chicago’s legendary gangsters and events like the Valentine’s Day Massacre via bus tours to notable sites led by sharply dressed gangster guides.
The list of “Things Chicago is Legendary For” continues with the comedy scene. Countless famous comedians got their start here, and hundreds of international comedy superstars from John Belushi and John Candy to Stephen Colbert and Tina Fey did their training at The Second City. Opened in 1959 as a small cabaret theater, the Second City has become the most influential comedy theater in the world. If you like to laugh, an improv and sketch comedy show at the Second City is not to be missed. But be sure to plan ahead, these hilarious shows routinely sell out!
Chicago is home to world-classical ensembles like the Chicago Symphony Orchestra and the Lyric Opera of Chicago, as well as superstar new music group Eighth Blackbird and the International Contemporary Ensemble. Chicago is also the birthplace of house music and although the club where Frankie Knuckles mixed his first house tracks in the late 70s is no longer there, you can still dance all night at plenty of other venues. Recommended: Smart Bar, one of the oldest and best electronic music clubs, where music is the focus and the dress code is lenient. Upstairs in the same building is the live-music venue Metro. Champion of every variety of “alternative” music, bands like the Smashing Pumpkins got their start here (the venue’s first show ever was a little-known band from Georgia called R.E.M. in 1982).
Chicago is also one of the best places in the US to hear the blues, and even has its own style, the aptly named Chicago blues. The award-winning Kingston Mines is the oldest and largest continuously operating blues club in Chicago, and you can hear some of the finest blues music there seven nights a week. Opened by Dr. Lenin “Doc” Pellegrino in 1968, the club is still run by the Pellegrino family. Doc himself, at 89, still lives above the bar and oversees the day-to-day operations. Minors are welcome with a legal parent or guardian, and there are plenty of special deals to take advantage of: there’s no cover charge for police, fire department, military, or anyone within 4 days of his or her birthday, students (21+) get in for free Sundays through Thursdays, and on Blues Alley Sundays, entrance here or at B.L.U.E.S. across the street gets you into both clubs all night.
Where to Eat
For your 24-hour breakfast needs, there’s no place more classic than the Golden Apple in Chicago. They’ve been serving up super-satisfying diner staples for more than 40 years, and the atmosphere is so inspiring that public radio show This American Life dedicated an entire episode to it. From blintzes to burgers, and bottomless coffee to milkshakes, it’s the perfect place for a pre-sightseeing breakfast or a post-concert snack.
Chicago. Pizza. Enough said? New Yorkers might try to argue that this three-inch tall, sauce-on-top concoction doesn’t count as “real pizza,” but whatever it is, Chicago deep-dish is delicious. Head to Giordano’s for a slice of what is repeatedly named Chicago’s best pizza—they have thin crust too.
Every time I’ve been to Chicago since 2004, I’ve eaten at Lula Café in the Logan Square neighborhood, and I swear it gets better every time. Lula Café was a pioneer in the Chicago culinary scene, and led the way for the farm-to-table movement. The atmosphere is a kind of anything goes casual elegance—the restaurant itself says it wants to be there for all occasions, from reading a book with a glass of wine to large celebrations. Menu staples like the pasta yiayia (bucatini pasta with cinnamon, feta, and garlic) and creative seasonal specials keep me (and everyone else who tries it) coming back.
If you only take one souvenir home from Chicago, take some Garrett Popcorn. The first shop opened in Chicago in 1945, and they’ve been making small-batch, handmade, secret-family-recipe popcorn deliciousness ever since. Go for a classic flavor, a seasonal special like Spicy
CheeseCorn®, or create your own mix. Don’t be deterred by the lines out the door—it’s worth it.
trivago Hotel Picks
To really get away from it all, stay at Ruby Room, a small, boutique spa hotel with insanely comfortable beds and no TVs.
If you’re looking for a rare taste of Chicago history, the luxurious Wheeler Mansion is your place. Built in 1870, it’s one of the last remaining stately mansions that survived the Great Chicago Fire, and was meticulously restored in 1999.
More on Chicago from Room5