Our Top 3 Picks: Italian Restaurants in Chicago

After living in Italy for a few months, I’ve naturally become biased when it comes to Italian dining around the city. Although my experiences have made me even more picky/snobby when thinking of dining for Italian, it has also helped me weed out the less competent places versus the gems around Chicago. Whether it’s for a romantic night out with your significant other, a last-minute dinner with girlfriends, or just a place for some good old-fashioned Italian menu items, I’ve discovered three locations around the city that personify my love for Italy and its cuisine.

Nico Osteria

Looking for a classy business dinner or just a fancy and “yuppie” kind of night? Try Gold Coast’s ravishing coastal-Italian-focused Nico Osteria. To be honest, my love for Nico was not immediate. I had went to its opening night early last Fall and  was not impressed by the menu nor with my overall experience. It was not until I had returned a month later that I began my love affair with this Gold Coast hot spot. Located in the heart of Gold Coast’s “viagra triangle,” Nico is an Italian seafood concept residing in the Thompson Hotel. Besides the beautifully decorated interior of both the dining room and Salone (bar concept in the back lobby), my favorite part of Nico is hands down, sitting at the chef’s counter. Not only is this my preferred seating, but I feel that sitting at the counter offers its diners the best experience, especially since you get to watch your own plate being made. With dishes such as the octopus fettunta (my all time favourite), the satisfying lobster spaghetti, and finishing off with Amanda Rockman’s mind blowing Nico Torte, Nico entices its patrons (especially me) with its fifty shades of deliciousness. Nico is usually booked every evening, so it’s best to check the 5:30 p.m. slot on open table reservations or even consider the weekend brunch, also equally amazing. There have been times where I’ve showed up at 7:30 p.m. on a Saturday and got a spot at the chef’s counter, so if you’re feeling brave, go for it.

Piccolo Sogno

Known as one of the most romantic dining destinations in Chicago, while still lending itself as a trendy and chic go-to for rustic Italian food, Piccolo Sogno continues to wow its visitors since opening their doors in 2008. Translating as “little dream” in Italian, Piccolo offers a wide-eyed variety of regional Italian dishes-from homemade pastas, hand-tossed pizzas made in its own wood-burning oven, to seafood, and desserts. Popular dishes and my personal favourite, is the (pictured)  Ravioli ‘Piccolo Sogno’, made with four cheese ravioli, pine nuts, butter, Marsala glaze, & Parmesan shavings. Another popular dish is the Branzino, a Sicilian sea salt crusted Mediterranean Sea Bass, whole roasted, served with citrus caper reduction and braised fennel. Although outdoor-eating-weather has quickly ended, the best place to sit is actually outside on their intimate and elegant patio area. However, during colder seasons, the interior is equally and comfortably decorated. Exposing rustic brick walls, showcasing rich blue accents, and hung with exquisite chandeliers all embodies Piccolo’s vibe  – simple, whimsical, and charming.  Since this is a heavy-date-night location, Friday and Saturday nights are definitely Piccolo’s busiest time frames. My recommendation is to check out Open Table for an idea of availability and better yet, other days to visit this quaint little Italian haven. 


Riccardo Trattoria

If you’re in the mood for a cozy, hole-in-the-wall restaurant serving dishes that remind you of, “just like it was in Italy,” look no further than the delightful Riccardo Trattoria. Residing in Lincoln Park, Riccardo’s is known around the city for its authentic Italian recipes (passed down through generations) and its “seductive dolce vida ambiance.” Perfect for a casual week night dinner or a small group dinner, the Italian-style trattoria serves up not only standard menu items, but it also offers “special” dishes daily. Open every day of the week for dinner until at least 10 p.m., special plates such as the simple, yet flavourful Tagliolini al Burro (my personal favourite), the cheesy Risotto Parmigiana, or Fried Eggs over Polenta & Fondue, are just some of the specialties Chef Michi whips up on a daily basis. Riccardo’s in so many words, is simple Italian done just right. No bells and whistles, just straight up comfortable and nostalgic flavours. Even the decor of the restaurant embodies that same vibe. Aged, rustic wooden furniture furnished with soft overhead lighting and walls covered with homey and pastoral framed art brought me right back to a neighborhood trattoria in Italy. Just as the other two locations, typical “date-night” time frames Thursday-Saturday evenings are usually booked, so keep an eye out on Open Table for an opening, or better yet, visit during the week instead. Who knows, maybe Chef would let you inside the kitchen for a preview.

Buon Appetito


©Aimee Gasior






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