The perfect blend of old-time tradition and swanky charm, Cindy’s Rooftop Restaurant is located in the Chicago Athletic Association hotel. The food, ambiance and social scene at the restaurant are great, but what makes this gem a top destination is the spectacular view of the city from the restaurant’s outdoor patio.
Unlike other iconic spots in the city, Cindy’s offers a view that encompasses Millennium Park, Maggie Daley Park, the Art Institute Museum and the iconic city skyline – all from one vantage point. Whether I’m enjoying the summer weather at brunch or escaping the cold for warm spirits indoors, I always make sure to spend time at the restaurant's outdoor fire pit and lounge to take in the beautiful city view.
Though little can compare to such city views, the atmosphere indoors doesn't disappoint. The space is enclosed with dome-window ceilings, allowing for natural sunlight to highlight the wood furnishings and natural décor, making the venue a warm, inviting atmosphere to enjoy the delicious food and drinks served.
For Sunday brunch, my friends and I usually order one of the sharable platters, along with a round of mimosas. If we’re there for lunch, we’ll likely share a few appetizers and entrées – our favorites being the Shrimp a la Plancha to start and the Lobster Roll or Seasonal Vegetable Torchio to share. For drinks, the restaurant offers a mix of elixirs and “potions”, as they call them – all of which add to the flavor and flare of this Chicago hot spot.
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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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