Walking down the bustling streets of Old Town, you're likely to pass their ratty, algae-green awning without a second glance—choose to take a peak and stop inside this dive bar, though, and you’ll be taking a seat among some of Chicago’s richest, most historic spots in the city.
Spend enough time there and you’ll become part of the walls… literally. One of the bar’s most notable features is the portraits of historic bar dwellers hanging throughout almost every inch of the interior. Located directly across the street from Second City, it’s no surprise that some of comedy’s most famed faces reign high above on the walls, including Tina Fey and Michael Shannon. These odes to Second City greats aren’t the only comedic references amongst the paintings—peruse around and you’ll see a naked Sarah Palin strapped with a rifle, international leaders in compromising positions, and a whole lot more.
My advice to first-timers? Grab a seat at the bar, order the negroni on ice, queue up an instrumental melody on the cash-only jukebox, settle in, and buckle up for a visual ride through the bar’s eclectic, famed story.
Whether you stop by for the notoriety or spend an entire day pleading your case to get your portrait painted, Old Town Ale House is one of my favorite spots to enmesh myself in the history, art, and unique company found in Chicago.
Find your way with 116 Insider Tips from our Local Spotters
The food here is prepared by Moses Sake, chef and co-owner of Tesfa, who learned how to cook from his mother. He runs Tesfa with his brother, Samuel Sake.
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I recommend getting the traditional breakfast combo, a sampler with three dishes, that comes with complimentary warm, crispy bread!
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The star of the show is De Luna's "volcano" taco, made with spicy poblano pepper and melted cheese. It may be one of the best tacos I've eaten in my life!
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Although this street is dominated by Vietnamese eateries, Nhà Hàng is a quieter, no-frills joint as opposed to the touristy, upscale restaurants nearby.
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Here diners sit in the naturally lit patio while enjoying traditional homemade Costa Rican food: sweet plantains, grilled veggies, rice and beans.
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My favorite thing to order here is the vegetarian arepa, which is stuffed with black beans, a generous portion of avocado, and sweet plantains.
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Founded in 1948, "Superdawg" is THE quintessential Chicago hot dog place - they'll bring your order right to your car, like they did in the '50s!
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The lentils are filling and creamy; the veggies are lightly cooked and nourishing; the injera bread is the perfect balance of slightly tangy and spongey.
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OMI has many good menu options, but their Japanese dessert toast is their all-star. Think of it as a fluffy French toast served with vanilla ice cream.
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Choose from multigrain sourdough, their house sourdough and miso rye sourdough; pastry choices include croissants, morning buns, and fruit danishes.
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Momos are bite-sized dumplings from Nepal and Tibet, usually filled with meat that is seasoned with spices like turmeric, garlic, cumin, and chili peppers.
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Their bread that has the perfect ratio of chewy on the inside and crispy on the outside. The 1979 multigrain sourdough is some of the best bread I've had!
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116 Insider Tips from our local Spotters
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