A Local’s Guide to Chicago

Venture beyond the city's iconic attractions and explore how the locals live.
 

 

Ask Chicago-based writer Lisa Lubin what she thinks are Chi-Town’s can’t-miss attractions, and she’ll tell you her city is all about the neighbourhoods. Here, Lubin shares three of her favourite districts and suggests how to spend your time in each one.

Andersonville

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The Swedish American Museum

This Swedish heritage ’hood on Chicago’s North Side has a mix of funky local boutiques, gastropubs and welcoming bars. It feels like a small village in a big city, with lots of unique businesses owned by people who live right in the neighbourhood.  

Compact and walkable, Clark Street is the backbone of the area, welcoming pedestrians with benches and a “people spot”—essentially a parking spot turned into a mini-park. Grab a coffee at the Coffee Studio or Kopi Traveler’s Café (with neat travel goods and books in the back) and then start strolling. If you’re lucky, the kitschy Puppet Bike will be out—literally a puppet show in a box on the back of a bicycle. Stop and watch for a guaranteed smile. 

The Swedish American Museum has immigration and art exhibits, language classes and performances. For more Swedish delights, try the Viking Breakfast at Svea restaurant and indulge in some European-style pastries at the nearly 90-year-old Swedish Bakery.

If you visit early enough for breakfast, the Bongo Room is where it’s at with a beautifully landscaped backyard and decadent breakfasts like white chocolate and caramel pretzel pancakes. For lunch, hit up Jerry’s Sandwiches, which also has its own quaint patio and a menu bursting with sandwich options. Don’t miss the popular gastropub Hopleaf. Not only does it have great grub like mussels and frites (my favourite in town), it has one of the biggest Belgian-focused beer menus in the city. A bit newer and trendier, Ombra and The Brixton have you covered for cocktails and small plates. 

Lincoln Square

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Merz Apothecary

Even more laid-back than Andersonville, Lincoln Square is an old German enclave that’s grown into a friendly, eclectic area with a tangible European charm.

Start your day at Café Selmarie, known for delectable homemade tortes and pastries, right in the heart of the square. Or try out the new Baker Miller Bakery and Millhouse, serving up sweet and savory goodies utilizing house-ground grains.

For some unique shopping, head to the Book Cellar (Is it a wine bar? A bookstore? It’s both!); Merz Apothecary, an old-timey drugstore founded in 1875 with an array of upscale products; and Timeless Toys for its unbeatable selection of classic toys, puzzles and books. 

Take a break at my favourite, somewhat-hidden spot: the charming, wood-clad, rooftop beer garden atop Gene’s Sausage Shop—a Polish-owned gourmet food market with perogies and smoked sausages galore.

For hearty German fare, you can’t beat the kitschy Chicago Brauhaus with its massive selection of schnitzel and its resident band, the Brauhaus Trio. A bit more upscale, Bistro Campagne has French fare and a delightful hidden courtyard, while Michelin-starred Elizabeth restaurant wows visiting foodies with a prix fixe menu of “new gatherer cuisine.” After dinner, catch a concert at the acclaimed Old Town School of Folk Music, or a film at the almost 100-year-old Davis Theater, one of the few remaining independently owned theatres in Chicago. And every Thursday night in summer, you can attend one of the free concerts in Gidding’s Plaza.

Wicker Park

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Big Star

Perhaps the most cutting-edge neighbourhood of the bunch, Wicker Park, once a more bohemian area, has become a truly trendy spot for creatives.

The Flatiron Arts Building, located at the epicentre of Milwaukee, North and Damen avenues, has served as an artists’ collective since the 1980s. You can see work by resident artists, as galleries and studios are often open to the public. 

Indie shops and boutiques also abound, from Reckless Records, with its vast selection of vinyl, to Transit Tees, great for unique shirts and other paraphernalia emblazoned with Chicago transit logos and maps. 

One of the best ways to tour the neighbourhood is on two wheels. Grab a Divvy bike from any of the nearby share stations, take a ride along the bike lanes on Milwaukee and Damen or hop on the new Bloomingdale Trail (opening in June), an elevated rail line turned pathway. Stop off in the actual Wicker Park, which is surrounded by lovely old mansions, and relax on a bench in front of a pretty 19th-century fountain. 

If you’re a foodie, Wicker Park is the best place to be—it really has become a dining mecca. Among my favourite hot spots are Rick Bayless’s new Xoco Bistro for some of the best-tasting Mexican tortas around, and Big Star, a honky tonk/hipster bourbon- and beer-focused taco bar with a bustling outdoor patio.

For drinks, try the Map Room for its huge selection of beers from around the world, or the Violet Hour, a gorgeous lounge (ahem, no baseball hats, no light beer, no cellphone use) known for some of the best cocktails in the city.

If you’re into live music, catch a show at the super-popular Double Door, or at the Hideout. For something a little different, you can get your game on at the Emporium Arcade Bar, combining your favourite arcade games of the 1980s and ’90s with a bar that offers a multitude of craft beers and a huge whiskey list.