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Local Spotting: Take a Trip to Our Favourite Spots in Chicago

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The Windy City. The Second City. Chi-Town and Chi-City.

At first glance, it seems that for every nickname the city of Chicago has (and there are still many others), there are dozens of sights to see, places to eat and things to admire in America’s third-largest city.

Anyone who’s only ever seen snapshots of Chicago on TV might conjure up thoughts of apartment buildings with train lines running adjacent, or deep dish pizza, or a bunch of guys in football garb sitting around a table exclaiming “DA BEARS!”

Ok, so Chicago is a first-rate sports city, that much is true, but the city is also steeped in history and culture, with art, theatre and music scenes that hold their own among the best.

We’re here to let you in on some of our favourite things to do. Here are a few of our top Local Spotting things to see and indulge in the next (or first) time you wind up in this great city.

The Museum of Contemporary Art (MCA) Chicago

Where to find it: Along East Chicago Ave, just before you hit the water beyond the scenic North Lake Shore Drive. Straddling the Near North Side and River North neighbourhoods, it forms a diamond shape on a map with Grand, Chicago and Clark/Division Stations — that said, it’s still blocks away from any of them, so we’d only recommend taking the “L” (what Chicagoans call their rapid-transit system) if don’t mind a bit of walk afterwards on a nice day.

Why we love it: MCA holds a special place in the art community, as one of the largest venues in the world dedicated to contemporary art, and home to its share of special moments in both the 20th and 21st centuries. In 1978, for example, MCA presented Frida Kahlo’s first-ever solo museum exhibition in the United States — not bad, huh? The famed museum features a collection spanning works from the likes of Andy Warhol to Jasper Johns, and genres from conceptual to surrealist. (Oh, and in case you were wondering: no, it’s not the museum from that scene in Ferris Bueller’s Day Off. That’s the Art Institute of Chicago.)

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Admire them on Instagram

Billy Goat Tavern

Where to find it: Counting suburban Lombard and O’Hare International Airport, there are actually eight locations of the famed Billy Goat Tavern, but the original location sits just north of where the Chicago River makes its grand entrance from Lake Michigan. It is, technically, on North Michigan Ave, but you’ll have to work a bit harder to find it. Look for a flight of stairs leading down under a nearby overpass, and you’ll spot a wood-carved sign and some neon lights to your right. As the sign inside says: “Enter at your own risk.”

Why we love it: If you’re looking for a good, old-fashioned cheeseburger, you’re in the wrong place — this place only serves the finest “cheezborgers.” If you’re old enough and fully in-tune with your pop culture sensibilities, you might remember a sketch from season three of Saturday Night Live wherein John Belushi and Dan Aykroyd play the owners of a diner inspired by, you guessed it, the original Billy Goat Tavern. This sketch put the Billy Goat on the map and patrons, both local and tourist, flock to sample some excellent cheezborgers, cheeps (fries… er, chips) and “No Pepsi — COKE!”.

View the original location on Google Maps

Admire them on Instagram

Chicago Architecture Foundation River Cruise

Where to find it: Docking takes place on the banks of the Chicago River, on the southeast corner of the DuSable Bridge on Michigan Avenue. Keep an eye out for a blue awning over a staircase that will lead you down to the dock along the Chicago Riverwalk. After that, the River and Chicago’s architecture awaits.

Why we love it: What better way to get a full view of the city in all its glory than to step foot on a boat and sail through the marvel that is the concrete jungle? Chicago’s First Lady Cruises, the company that runs the tours in conjunction with the Chicago Architecture Foundation, packs a lot of knowledge on how the city came to be into a fun, family-friendly 90 minutes.

Chicago river cruise

View the docking location on Google Maps

Check out Chicago’s First Lady Cruises on Instagram

The Second City

Where to find it: In the heart of Old Town, at the corner of North Wells St. and West North Ave. If you miss the banner high above that reads “The Second City” in your peripheral vision, you’ll immediately spot the three archways ushering you into this Victorian-era building.

Why we love it: If you have a favourite comedic actor or actress, there’s a decent chance that they came from the comedy factory that is The Second City Chicago. Boasting graduates including Tina Fey, Amy Poehler, Steve Carell, Stephen Colbert and Bill Murray, this Chicago landmark continues to put on some of the funniest comedy shows anywhere in North America.

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