Growing up in New York, more specifically, the Italian-American mecca that is Long Island, I am very attuned to Italian (aka Italian-American) cuisine. I have very high standards for what constitutes an Italian-American family meal and the quality and selection of offerings at restaurants.
Italian seems simple enough: pasta + sauce = delicious, but no, not all restaurants are created equally. For those with discerning tastebuds, differentiating pre-packaged sauce from a homemade sauce is easy, but if you can't do that, I'm here to help you.
Also, don't even get me started on pizza (which is a food group all of its own). However, there is a distinction between what is considered pizza: deep dish is not the same as thin-crust. These are two completely different things! As a transplant from New York to Chicago, I do not like the thin crust here, that is a universal truth. However, I do not hate deep dish pizza, in fact, I kinda like it (especially compared to the debacle of thin-crust here. I will die on this hill).
So, here are 4 Italian restaurants that have satisfied my quest for Italiano in Chicago + 4 sufficient pizza recommendations.
Nonnina: 340 N Clark St (River North)
Best Place for Girls' Night
I have been to Nonnina multiple times. Located about a block away from the river, you get all the charm of bustling downtown views, great photo ops, and an easy central location. It is relatively easy to get a reservation, the decor has an intimate yet fun charm, and the food and prices are quite affordable. Two of the highlights to level up your girls' night are the cocktails and the appetizers. I love the Giovanna (almond + raspberry) and if you have 2 of those, you're sure to be in a great mood. The cheese plate (and cured meat board) are $18 each and are ample amount for a group of 3-4. Also, as a fun bonus, happy hour is on weeknights from 3-6 pm with $5 off antipasti, $6 house wine, and $7 cocktails. As for entrees, try the Mafalde, Buccatini, and Carbonera.
Bonus points for offering brunch and doggy menus! This is a go-to spot for you and your girls and your trusty canine companions!
Calo Ristorante: 5343 N Clark St (Andersonville)
Best Old School Italiano
When I think about the expectations of a New York Italian restaurant, Calo takes me right back. So much so, that I was able to declare that my dad would enjoy it here (and he's tough to impress). The place is big and always busy, and there are large groups and large portions. The menu is quite extensive, making it difficult to make a choice, so it's helpful to glance around the dining area and see what others have ordered. If dining in isn't your thing, Calo levels up with nightly take-out and delivery specials. I recommend trying the ziti vodka which is enhanced with peas and sundried tomatoes.
Monteverde: 1020 W Madison (Fulton Market/ West Loop)
Best Food
I just went to Monteverde on a date and that is what inspired me to write this list. I was just so dang excited about the food that I wanted to share with whoever would listen (besides my Yelp community). Monteverde might be my favorite rustic version of Italian food. This place is one of the most difficult locales to obtain a reservation (you can use Resy, and walk-ins for the bar are welcome when possible). I want to offer some recommendations for food, but first I need to rave about the stuffed cabbage appetizer. This is my mom's favorite food, so I had to try Monteverde's version of a home-cooked familiar. Wow, it exceeded my expectation with a soft textural experience with all flavors both melding and brightening together. I was so impressed because I've never seen this old-school classic on menus. Beyond that, be sure to check out the scallop appetizer, tortellini in brodo (its a soup, but on the entree list), and. be prepared to end with the amazement of their gigantic flavor-explosion tiramisu. This place is not to be missed.
Bonus: They have a mercato where you can purchase fresh or dried pastas, cocktails, and cheese to-go. They also offer a gluten-free menu.
Hot Tip: See if your credit card offers concierge or dining privileges; it might help you to snag a reservation.
Alla Vita: 564 W Randolph (Fulton Market)
Best Date Spot + Best Restaurant Pizza
The food here is exquisite but the ambiance is not to be missed. When you walk in and look up, the ceiling is detailed with hanging drapes that look like a canopy made from the face of roses hanging all over the restaurant, or comparable to a desert painting by Georgia O'Keefe- in short, very artistic and luxurious. However, off to the side is a separate space that is more like a garden solarium with plants strewn about the rafters and large bright windows. I prefer this side area because it is much more romantic and intimate than the main dining room, which is very "see and be seen."
Start off with a Flower Crown cocktail, dangerously delicious and sneakily strong. Must-try foods include: tuna crudo (love the lemon oil), burrata (paired with an asparagus salad), arancini (very rich), tagliatelle, ricotta dumplings (most popular menu item), and roasted broccolini. Now, for something that will surprise you. The thin crust pizza here is in a league of its own. I've never had pizza crust that is so crispy yet soft and airy on the inside. The mushroom pizza is extremely pungent yet equally delicious. Finally, reservations are an absolute must, so plan well in advance.
Hot Tip: Almost all of their food reheats well, so my recommendation is to maximize and over-order and then take home lots of leftovers. However, the ricotta dumplings do not reheat well at all. They're very rich, so maybe order these as an appetizer and share with the table.
Jet's Pizza: Franchised around Chicago
Best Take-Out Pizza
I will take an 8-corner Turbo Crust Detroit-style pizza from Jet's literally any day of the week. Order it with extra marinara or dipping sauce on the side and you are in heaven. Jet's / Detroit-style is my happy medium between Sicilian-style NY thick-crust-pizza and a midwest propensity for deep pizzas, with the added pizzaz of a butter-fried crust. They usually offer specials, so you can get pizza, cheesy bread, and a 2L of soda for under $35.
Bonus: Jet's is open late night at most locations.
Happy Camper: Multiple Locations Around Chicago
Best Bar Pizza
Ok. So this place was a happy surprise. I've been here many times for drinks. It's super casual with sparkling and eclectic decor (hello, we love a disco ball, end even better, multiple disco balls), while playing many sports games on large TVs that can be seen from almost every vantage point and angle in the bar. However, I can't believe that I overlooked the pizza for so long (probably in part because I'm a pizza snob). The menu offers a large selection of pizzas, including ample vegetarian pizzas. I highly recommend adding roasted garlic cloves to your pizza, they're so sweet and delicious! The crust is very similar (though not as dramatically impressive) to Alla Vita's, so it's a perfect lower-budget alternative. Add a side of marinara to dip the pizza, *chef's kiss*.
Gino's East: Magnificent Mile and South Loop
Best Chicago Deep-Dish
I'm here to start the fight, Gino's East is the best deep-dish in Chicago. In a city that is synonymous with deep dish, Gino's differentiates itself by using a cornbread crust with a texture that amplifies the experience of eating this Chicago delicacy. I'm super bummed to report that they're only down to two operating restaurants in Chicago, but they're still top in my heart. However, it appears that their production of frozen Gino's products (available at grocery stores) and nationwide shipping are allowing Gino's East to proliferate beyond the borders of Chicago.
Gino's is the best. I said what I said.
Lou Malnati's: Multiple Locations in Chicago
Honorable Mention: 2nd Best Deep-Dish
Because I am mostly alone in my aforementioned affinity for Gino's East, when dining for deep dish, I mostly find myself with the far less polarizing Lou Malnati's. I like "The Lou" which is a veggie-lover's delight. Pair this with a house salad and dip your pizza in the balsamic dressing- yum.
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