Todd Snyder and Blogger at Chicago Mural

We Went to Chicago With Designer Todd Snyder and Blogger Jess Keys and Ate…Everything

You might recall our wicked awesome trip to Boston, where we celebrated the Local Pride by Todd Snyder collection with Todd Snyder himself. Well, we hit the road once more, this time with Todd and Windy City blogger Jess Keys of The Golden Girl. And when we say we were blown away—we mean it literally.

With Jess leading the way as resident Chicagoan, we took a bite out of the city, one deep-dish pizza at a time. The local mom-and-pop shops and restaurants she showed us offered exactly the kind of local flavor and personal connections that inspire Todd. For this round of clothing, Todd chose sayings like “I am the Sausage King of Chicago” (courtesy of the one and only Ferris Bueller, of course) and motifs depicting well-known places around the city. Tag along below to see where we went, and tell us your favorite Chicago spots in the comments!

Elaine’s Coffee Call

First up, Elaine’s Coffee Call for a pastry and some caffeine! This quaint coffee shop was cozy for a morning pick-me-up. We sipped our espresso while Jess mapped out our plan for the day.

Lakefront Trail

With calming views of boats bobbing in Monroe Harbor, Chicago’s Lakefront Trail was the perfect place for a mid-morning stroll. We snapped some photos along the edge of the water and took in the scenery as cyclists and runners passed by. 

Cloud Gate at Millenium Park

No trip to Chicago is complete without stopping by Millennium Park to view Anish Kapoor’s Cloud Gate sculpture. Made of stainless steel plates welded together, the reflective artwork is affectionately nicknamed The Bean! Selfies encouraged. 

Gino’s East

Bagels are to New York what deep-dish pizza is to Chicago—you almost can’t have one without the other. When we walked into Gino’s East, one of Chicago’s most famous deep-dish pizza purveyors, we were hypnotized by the gooey pies coming out of the kitchen. We devoured a Gino’s Supreme and a cheese pizza, and afterward, signed our names on Gino’s graffiti’d walls.

Logan Square Mural

On our way to Reckless Records, we swung by Milwaukee Avenue and Prindiville Street to snap a few photos in front of The Greetings Project’s “Greetings from Chicago” mural. Painted by NYC graffiti artist Victor Ving, the mural took four days to spray paint!

Reckless Records

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Reckless Records is a super hip shop that originated in London and came across the pond in 1988. We spent the afternoon flipping through the stacks and reminiscing about our favorite songs!

Superdawg Drive-In

Last stop on our grand tour of Chicago…Superdawg! Driving down North Milwaukee Avenue, it’d be hard to miss the two winking papier-mâché hot dogs perched atop Superdawg’s harlequin diamond-patterned restaurant. The statues—Maurie and Flaurie, named for the owner and his wife—have been there since 1948 when Maurie started the carhop hot-dog stand while studying to be a CPA. 

As we approached the restaurant, current owner Don Drucker greeted us. He’s the son-in-law of the founders and the brand’s best historian. He joined us as we devoured everything on the menu (and we mean everything…we had three different flavors of malts, Superdawgs, SuperFries, Superonionchips, Superveggies and split a Whoopskidawg!) telling us stories from the last 67 years of business.

Stop by your local Chicago store and pick up Todd’s Windy City-themed designs!

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