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Stay in The Loop: your guide to Chicago

With a skeleton of skyscrapers and L tracks, and a heart that beats (and breaks) for ketchup-free hot dogs and hometown sports teams, Chicago—nicknamed the “City of the Big Shoulders” feels like the urban Midwest personified. And there’s no better time to make its acquaintance than at Showcase Chicago on July 18 at the Revel Fulton Market.

When you’re not hearing from customer service leaders at Zendesk, MoviePass, and ActiveCampaign, or anticipating the next waves of customer experience, you’ll find plenty in and around The Loop that entertains, enlightens, and provides respite from Chicago’s legendary humidity.

Public art in Millennium Park. If you went to Chicago but didn’t take a “bean” selfie, were you really there? In all seriousness, Cloud Gate is a brilliant, interactive work of art, upending notions of horizon, cityscape, place, and self with its curvy, reflective surface. In this era of Instagram-driven experiences (instead of good old-fashioned experience-experiences), it gets extra kudos for fueling the latter since 2005.

Also interactive and just as interesting: nearby Crown Fountain, a combo of public art, wading pool, hat-dunking station, and people-watching spot with plenty of tree shade and grassy seating.

Intelligentsia Monadnock. Chicago-based indie roaster Intelligentsia recently joined Peet's Coffee and Tea, but continues to operate independently, delivering a variety of South American and African coffees from six locations, including this one in a cool building in the middle of the downtown hustle-bustle: Intelligentsia Monadnock (pronounced muh-NAD-nock).

Architecture and L tracks. There is no shortage of cool structures to keep your neck craned. The skyscraper was born here, the city’s skyscape is recognized the world over, and advances in construction—such as the steel framing in commercial buildings—are unparalleled. Specifically, take a gander at some ornamental Art Deco and examples of the Chicago School of Architecture’s namesake style on one of the city’s many river cruises. You can also walk along The 606: an elevated park and walking path on a repurposed train track.

Little Goat Diner (or Girl and the Goat if ya fancy). At Little Goat Diner, sit at the counter for appropriately diner-style fare; special hats off to the chicken po-boy with coleslaw and local beers on tap. Pop into the adjacent retail store, which is also a bar if your whistle requires additional wetting, for funky-chic kitchen merch and an impressive variety of spices to bring home. I bought This Little Goat Went to Grillville and regret nothing—other than the fact that I didn’t buy more.

The Aviary. If you’re looking to treat yo-self, try this high-end cocktail bar in Fulton Market, a stone’s throw from the Showcase Chicago event venue.

Haymarket Pub and Brewery. Cocktails not your thing? Not far from The Aviary, you’ll find Haymarket Brewery in West Loop. Don’t miss out on the back room for some live music.

Chicago Riverwalk. The Chicago Riverwalk boasts 1.25 miles of walking path. Host to many a tour boat and restaurant, there are also pockets that are perfect for people watching, particularly at its Y-shaped split near River North.

Topolobampo. It happens, without fail, to San Franciscans: we see Mexican food anywhere in the world and find ourselves pulled into its orbit. On a recent trip, I couldn’t pass up Topolobampo in River North, which provides more than satiation for fans of the cuisine. Boasting Michelin-star cred, it’s a great spot for a celebratory team lunch or dinner.

Of course, there is also pizza. Giordano’s and Lou Malnati’s, Chicagoland deep dish mainstays since the 1970s, have multiple locations across the region. I enjoyed my Giordano’s pie, but must admit it’s something I rarely seek out, especially when traveling solo. But if deep dish is your thing, there’s also Chicago Pizza and Oven Grinder, serving up pizzas that are more like pot pies.

Up next, Showcase Sao Paulo.

Tara Ramroop is a content marketing manager at Zendesk and frequent contributor to Relate. A loquacious Libra lady of letters, she firmly believes the craft of storytelling makes the world a more understanding and, well, relatable place. As a Bay Area native, English degree be damned, she has no qualms about saying or writing "hella." Follow her visual stories and occasionally cheeky captions on Instagram @roopisonfire.