Weekend Itinerary: Chicago for Design Lovers

Design Features

Yes, Chicago is home to The Bean, aka Anish Kapoor’s iconic “Cloud Gate” sculpture in Millennium Park. But the city is also where you’ll find some of the most innovative art, architecture and design in the country. Here are just a few of our favorite places to get you through a whirlwind, windy weekend.

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A photo posted by hotellincoln (@hotellincoln) on

Every design-centric adventure needs a visually striking home base, and Chicago has plenty that fit the bill. You’ll have to book early to snag one of the six rooms at The Longman & Eagle Hotel ($85+), located in the Logan Square neighborhood. Each room is unique, but you can count on great art, gorgeous bath setups (walk-in showers, clawfoot tubs), and luxe toiletries. Downstairs you’ll find a rustic whiskey bar and restaurant with more than 300 types of brown water, and behind the hotel Off Site Bar is perfect for a quick bite. Don’t miss their Donut Shop pop-ups on the weekend.

For a more vintage vibe, try the Hotel Lincoln, a historic spot that was completely renovated in 2012. Rooms offer views of Lincoln Park and Lake Michigan, but the best vista is upstairs at the hotel’s J. Parker rooftop bar, where you can sip a Sazerac nightcap while gazing out over the city.

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Start your day off at one of Dark Matter Coffee’s three locations, where you can order up a draft iced coffee or Mayan Mocha; be sure to grab a bag of barrel-aged coffee to take home. Head to Bang Bang Pie Shop for a selection of sweet and savory pies (like Ginger Rhubarb Crumble), or try Dove’s Luncheonette for Southern-inspired Mexican cuisine with a side of Mezcal. For dinner, the stunning three-story Japanese restaurant Momotaro puts as much emphasis on its design as its ambitious food program. Wrap up your night at swanky cocktail bar The Aviary, where the bartenders are trained as chefs, or the slightly more low-key Maude’s Liquor Bar.

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A photo posted by @vividbraille on

Like a shopping mall for design lovers, Andersonville Galleria boasts more than 90 vendors hawking jewelry, art, gifts, antiques, gourmet goods, and more. For a modern, eclectic selection of local art, clothing, jewelry, housewares, and more, head to Dovetail in West Town. The community-focused shop regularly hosts trunk shows with local designers. Humboldt House stocks vintage and modern furniture, textiles, and Chicago-made goods. You never know if you’ll walk out with a dagger cuff, a handmade bowl, or a set of antique school chairs. Artpentry is a woodshop/gallery where you can find paintings, prints, and hand-painted T-shirts. Vividbraille is a boutique and creative studio that carries footwear and apparel along with screenprinting classes. On Sundays, head to Dose Market, a weekly showcase of local makers, bakers, artists, designers, and more.

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Oh how we love Millennium Park. Great pic by @tzimmylynn

A photo posted by ChicagoArchitectureFoundation (@chiarchitecture) on

Of course, you have to do the tourist thing at Millennium Park while you’re in town, and if you’re a sports fan, you have to see Wrigley Field. For more design-y experiences, try the Chicago Design Museum and the Museum of Contemporary Art. Get a taste of the local gallery scene at the free Renaissance Society at the University of Chicago; this summer they’re featuring Bogota artist Gabriel Sierra. And for a closer look at the city’s famous architecture, try one of the Chicago Architecture Foundation’s architecture tours.

What did we miss? Leave your favorite Chicago design destinations in the comments.

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