CH Local: Chicago

From modern haberdasheries to hole-in-the-wall taquerias, our latest jumping-off points for navigating the Second City

Known alternately as the Windy City and Second City, Chicago may be more known for what it isn’t (New York), than what it is. Home to the third-largest South Asian, Mexican and Puerto Rican populations in the U.S., a just-announced bike-sharing program and a growing cast of restaurants serving up much more than just deep-dish, there’s plenty of reasons to check out the northerly metropolis. Get the rundown on what to do while you’re there in our newly-up-to-date CH Local guide, which includes the standout joints below.

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Shrine Haberdashers

Upstairs from Jack Spade’s Oak Street shop is Shrine Haberdashers, a well-edited boutique stocking handcrafted artisan accessories (pocket squares, rings, cuff links, etc.), leather goods, ties, hats and scarves. An excellent spot for sourcing hard-to-find accessories, gifts or other dapper duds, the Shrine and Spade combo is a great place for guys to pick up some classic threads.

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Andersonville has become known for its eclectic mix of vintage furniture and housewares shops like Scout and Roost, but a newcomer arrived in 2010, adding a bit of edge to the Far North Side young professional enclave. Transistor, owned by husband-and-wife duo Andy Miles and Rani Woolpert, is a multi-use space. Framed photos of live music gigs and urban scenes grace the walls; letterpress stationary and cutting-edge turntables line the shelves; and hard-to-find music magazines and hardcover culture coffee table books abound. And, depending on the day, Transistor hosts live radio shows, comedy performances and film screenings.

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Big Star

Edging out Rick Bayless’ River North spot Xoco for down-and-dirty Mexican street food, Big Star (from the team behind Avec, Blackbird and the Violet Hour) is a must-hit for tacos al pastor, tacos de pollo and tacos de pescado. Dig in to the always-fresh guacamole, queso fundido and pickled vegetables, and wash it down with a super cheap beer or choose a shot of whiskey from their extensive list of Southern-inspired spirits. Take some tacos away from the walk-up window, or stake your claim on the sprawling patio in the summertime and soak up some rays.

Images of Big Star by Chris Tsuyuki