To kick off week two of our newest series A Date in the City, we’re going just a hop, skip, and a jump away from New York City to its unofficial little sister: Chicago. The hub of all things Midwestern and home to one of the most diverse and cosmopolitan city centers in America, Chicago is the place to be for a low-key day in the city.


Now, of course, Chicago like any other big city, has a reputation which precedes it. For Chi-town, this reputation consists of deep, deeeeep dish pizza, Lake Michigan, and the Cubs. We’re here to highlight everything else this pared-down city has to offer. And it’s a lot.

Before we even get to brunch, it’s worth noting that Chicago has one of the best paths for running (or strolling) in a city. Right on Lake Michigan, go for an early morning jog on Lake Shore Drive and let the views fuel you as you prep yourself for a hearty plate of pancakes and at least a few mimosas.

For brunch, we have options, options, and more options. If you’re feeling something lighter and more laid-back, try Dove’s Luncheonette. This spot has gained a cult following, due in part to its throwback, diner style atmosphere. But what really seals the deal is their Mexican-southern fusion take on brunch. From breakfast tamales to barbacoa enchiladas, anything goes at this one-of-a-kind brunch spot. And if you’re feeling the particularly horrible after effects of a night out, try their famous “Back to Life” cocktail. I guarantee it’s not what you think. It’s so much more.

If you’re anything like me and hold the belief that brunch is the epitome of meal times, then maybe you should take brunch to the next level at Jam. This is the highest of the high-end brunch menus. Try the lamb and grits to really solidify the classiness of your morning, and let the smoked salmon keep you feeling posh all day long.

Ready for your daily caffeine fix? Try Buzz: Killer Espresso on North Damen Avenue for great espresso and an even better staff. You can tell the baristas here live and breathe coffee and are just dying to craft the perfect cup of joe for you. From your bitterness tolerance to your milk preferences to your favorite dinner spot in the city, the baristas glean it all and pour it straight into your latte with the perfect finishing flourish. And if you’re hoping to get some work done or whisper sweet nothings in a quiet corner, Buzz has two floors of space in which to spread out, isolate yourself, and enjoy your drink.

If you’re a theatre buff head over to Navy Pier’s Chicago Shakespeare Theater and catch a show of anything from King Lear to Waiting for Godot. The current flavor of William Shakes is actually Madagascar, adapted from the DreamWorks film. If you're feeling something a bit heavier--and a bit more classical--you can also catch a production of Romeo and Juliet at Shakespeare in the Park. I recently got to sit in on a performance of Love’s Labour’s Lost at Chicago Shakespeare Theater and was thoroughly blown away by the quality and integrity of the performance. As a complete Shakespeare nerd, I can guarantee that you’ll feel transported back to the Elizabethan era watching these players play.

Craving something sweet after a long and emotionally tumultuous play? Check out Snow Dragon Shavery right in Navy Pier for a macaron ice cream sandwich (pictured above), that will change your life. Prior to my trip to Chicago—and after striking out in New York City—I had thought the only place I would find a macaron ice cream sandwich would be in France, but voila! I, of course, had to pick the classic pistachio ice cream sandwich, but their flavors range from vanilla to the quintessentially Midwestern Superman, to rose. Snow Dragon Shavery also offers regular macarons, bubble tea, shaved snow, and ice cream, so stop by to fulfill all of your sweet dish dreams.

For drinks, pay homage to Chicago’s legendary blues roots at Kingston Mines in Lincoln Park. Live like a true Chicagoan for a night and indulge in beer, barbeque, and the blues. With performers each night harkening back to the good old days of soul and rock & roll, you’ll find yourself settling in nicely to the laid-back atmosphere that is so integral to the city of Chicago.

You can find something never-before-seen around every corner in Chicago. Add on the rush of the big city and the slow-moving, contented attitudes of the native Midwesterners and you’ve got an inimitable combination unique to Chi-town.

What are some of your go-to locales in Chicago? Drop me a suggestion or review one of my favorite spots in the comments below!

Until next time, daters.


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