Gibson's Italia is an overachiever. There's not just that great Gibson's steak but platters of crudo, towers of shellfish and delicate house-made pasta. On three levels. With two fireplaces and a roof deck that wows with skyline and river views. The antipasti selection seduces from arancini made with one year aged risotto to lighter-than-air meatballs and pasta is hand made daily with Italian heritage organic stone-ground flour. Healthy eaters will go for oven roasted veg or an Italian Grain Bowl with arugula, farro, barley, lentil, black-eyed bean, avocado and dried flower pollen. Hearty panini ranges from grilled eggplant and zucchini to Italian Prime Rib. If you're indulging infrequently or it's a special occasion, consider the pure Japanese Kobe cut to order. It's all fabulous since everything is USDA Gibsons Prime Angus. Choose among 25 wines by the glass or a Midwest whiskey from a small-batch distillery.
Recommended for Italian because: It's everything you love about Gibson's plus sophisticated Italian dishes, an extensive wine list and drop dead gorgeous looks.
Jacky's expert tip: The name "Gibson's" is synonymous with steak, but vegetarians have fantastic options like the new Caramelle pasta and cauliflower with cheese fonduta, chive oil, hazelnuts and shallots.
The intimate and casually romantic dinner spot serves delicious Italian food from the Piedmont region of Italy (bordering France and Switzerland at the foot of the Alps). The tiny dining area is lined with white lights and candlelit tables. The eatery is best known for fresh pasta, which Chef Cameron Grant learned how to make in Langhe, Italy. Other popular choices include a favorite of the region - raw Piemontese beef, cured egg yolk, crispy shallots and rosemary cracker bread. Piemonte produces high-quality hazelnuts so opt for any dessert featuring the rich nut. Piedmontese wines, like Barolo, can be redolent of cherries, roses and love, so order a bottle!
Recommended for Italian because: Osteria Langhe serves exceptional, seasonal, Piemontese fare and the lush wines of the region in a completely comfortable setting.
Jacky's expert tip: Chef offers Trifecta Tuesdays: choose an antipasti, a secondi and a dolci from the dinner menu for $38.
Piccolo Sogno, Italian for "little dream," is just that. The first restaurant of partners Tony Priolo and Ciro Longobardo is still satisfying diners after 11 years on the competitive Chicago dining scene. The menu is studded with hand-made seasonal rustic Italian dishes and an impressive all-Italian wine list checks in at over 400 varieties. The River West eatery, with its serene interior and shaded patio, provides an intimate refuge from the noisy city streets. Lucky you - it's open for lunch Monday through Friday and dinner seven days a week. The menu is full of incredible dishes from an earthy Ribolitta (twice cooked Tuscan bread and vegetable soup) to ethereal pasta like toasted flour ribbon pasta tossed with mixed mushrooms, herbs and Parmesan. Locals rave about the whole Branzino sided with braised fennel and wood-fired pizzas.
Recommended for Italian because: Piccolo Sogno is an excellent Italian restaurant lauded for its fresh rustic fare, outstanding service and one of the most enchanting patios in Chicago.
Jacky's expert tip: Parking is free at lunch and $13 at dinner which is a bargain. Or take a taxi to River West - you won't be disappointed.
For Northern Italian cuisine, Tuscany is a fine choice in Little Italy that's as popular with Millennials as it is with business folks and families with grannies and kids. The Phil Stefani classic has delivered rich Tuscan flavor and juicy Italian wines to Chicago for over a quarter century. During brisk Chicago winters, the scent of wood-fired gourmet pizzas is positively heavenly. Enjoy a menu curated by Executive Chef Victorio Padilla: one-of-a-kind pasta dishes like the popular Ravioli Pera (roasted pear, Parmigiano, toasted nuts, sun-dried tomatoes, mascarpone cream); perfectly prepared steak, veal and chicken dishes; as well as fresh seafood. In the summer, get a seat on the elevated patio offering the sights of Little Italy. Consider ordering a glass from Phil's favorite hometown vineyard - Fattoria di Montechiari. The restaurant also has two suburban locations, in Oak Brook and Wheeling.
Recommended for Italian because: Not just for locals, Tuscany has wowed out-of-towners such as former President Clinton and former Vice President Al Gore.
Jacky's expert tip: Tuscany is open for lunch on weekdays only. Consider drink and appetizer specials in the bar from 4 – 7 pm Sunday – Thursday.
At the intersection of Texas, Italy and Top Chef, you'll find Monteverde, Chef Sarah Grueneberg's ode to her birthplace, wanderlust and the inventiveness that tv viewers witnessed on season 9 of the Bravo show. If you're looking for traditional dishes, you're in luck but there are also adventurous new flavors not usually seen in an Italian kitchen. You may get religion trying handcrafted pasta made fresh daily - either classic Italian pastas or Grueneberg's innovative riffs like wok-fried arrabbiata or tortelli verdi with roasted white miso. Nibble Stuzzichini (snacks), primi piati (before pasta), sizable entrees and dessert. Oma's Green Mountain Salad is full of seasonal crunchy vegetables served with a family dressing recipe with house-made lemon pepper and garlic salt. Try an updated version of Chef's grandmother's dish, Lillian's Stuffed cabbage redolent of mushroom bolognese, a vegetarian choice that is as hearty as any meat dish.
Recommended for Italian because: Near the United Center, choose Monteverde before a game or concert for exceptional snacks or a big bowl of Ragu Alla Napoletana feeding 2-4 people.
Jacky's expert tip: There's always room for walk-ins - the bar and patio serve the full menu on a first-come, first-serve basis.
RPM Italian is celebrity-owned (Bill and Giuliana Rancic), but don't hold that against it because it's a great Italian restaurant in Chicago close to hotels, shopping and Michigan Ave. RPM's space is outfitted in modern black, white and grey decor. It's known for a housemade pasta program, featuring more than a dozen seasonal pasta at any given time. Start with one of the signature cocktails or a bottle from an extensive wine list, and then choose from the housemade pasta like Maine lobster ravioli and seafood risotto evocative of Mediterranean, slow-roasted meats, wild fish and seafood and Italian classics with just enough contemporary flair to make it sensually interesting. Don't think twice about paying for bread because the truffled garlic bread circa 1963 is transportive. RPM Italian was recently named one of OpenTable's Top 100 Restaurants in America. Steaks are impressive (the sister restaurant is RPM Steakhouse) as is service.
Recommended for Italian because: Excellent food and service make this stylish. modern restaurant in the heart of tourist-heavy River North a fine choice.
Jacky's expert tip: Stop by the bar weekdays between 4-6pm for Apertivo Hour for $5 "cicchetti" like Provolone stuffed peppers and Big Eye tuna.
We can bet that some of your favorite Italian dishes are Roman: Cacio e Pepe studded with black pepper and Pecorino Romano cheese; Bucatini all'Amatriciana starring spicy pork cheek ragu; and eggy Carbonara. You can get exceptional versions of all as well as other Roman delights like crispy Jewish style fried baby artichokes, stuffed rice croquettes (Suppli) and an array of different meatballs at Bar Roma. Chef Fred Ramos (Printer's Row, Gioco, Angelina) steers the gondola at the Andersonville charmer that features a tavern style bar/lounge and an open kitchen dining room. In addition to perfectly executed Roman cuisine, expect interesting craft cocktails and a wine listed curated by one of the top somms in town.
Recommended for Italian because: Bar Roma is everything one could want in an independent neighborhood Italian eatery: warm and welcoming, with outstanding food and wine.
Jacky's expert tip: In addition to dinner nightly, Bar Roma offers an exceptional happy hour and (bottomless) bubbly brunch on Sundays.
Quartino calls itself, "Chicago's Italian restaurant" and if you've never been you might think that a tad presumptuous. It's not. People love this place as evidenced by tables filled with chatty diners every night of the week. Unlike too many other River North eateries, Quartino offers exceptional food at reasonable prices. Waitstaff can be slammed but still attentive and cheerful. There's wonderful artisanal salumi, cheese and olives, delicate house-made pasta, a quartet of risottos prepared with aged rice from Piemonte and countless Neapolitan thin-crust pizzas exiting the kitchen. Hearty specialties include farmhouse chicken and braised pork shank or go light with wine bar plates such as veal meatball slider, polenta fries with red pepper dipping sauce and house-made goat's milk ricotta. Tasty classic and specialty cocktails, Italian sodas, a deep wine list and a dozen decadent desserts including dark chocolate fondue round out the perfection of Quartino.
Recommended for Italian because: Quartino has it all: winning wine and food, attentive service, cheery atmosphere and reasonable prices.
Jacky's expert tip: Stop by for lunch ($8 sandwich special) and the weekend brings Italian brunch items like a Tuscan skillet and house-made stuffed zeppole.
How does Chef/Partner Tony Mantuano continue to crank out the most ethereal pasta, sophisticated antipasti and jaw-dropping second courses after all these years? He cooks from the head and the heart and is smart to hire simpatico creative chefs like Season 15 winner of Top Chef, Joe Flamm, a south sider making Chicago proud. Ideal for date night, Spiaggia offers Mag Mile and Lake Michigan views coupled with simple but expertly created dishes featuring seasonal produce and delicate, handmade pasta. Service is impeccable and desserts irresistible. Cafe Spiaggia, on the same floor, is a sweet European cafe with calming colors and an equally inviting menu. Wonderful shared plates include Emilia Romagna on a Plate (puffed fried gnocco, Prosciutto, fonduta and balsamico); or try fried peppers, fennel and smelt. Outstanding hand made pasta like lumache with lamb Bolognese and Parmigiano Reggiano make you a pasta amnesiac for all other noodles.
Recommended for Italian because: Attention to detail, thoughtful cookery, fine wine and fetching views make the restaurant and cafe wholly memorable.
Jacky's expert tip: This is one of Chicago's finest restaurants, so be sure to reserve a table and don't overlook Cafe Spiaggia for lunch or dinner.
Puglia is a wealth of rustic cuisine, juicy wine, plentiful seafood straight out of the Adriatic and stunning vistas. Osteria Trulli is the only authentic Pugliese eatery in the area via chef/owner Giovanni DeNigris, a native of the region. Warm crusty bread and chewy, slightly charred pizza exit the wood-fired oven filling the charming space with heavenly aromas. Ingredients are imported from Puglia (or made on site) including the luscious burrata on pizza (with organic arugula, cherry tomatoes and mortadella) - simple and exquisite. Eggplant (melanzane) rolled around spinach and bread crumbs then doused with pomodoro sauce melts in your mouth. Chef shuns butter and cream so homemade gnocchi is bathed in a melange of mascarpone and broth reduced to a dreamy consistency. Nuclear-sized Adriatic prawns baked in the wood oven are surely Instagram stars. Finish with heavenly dessert, homemade limoncello and Pugliese espresso and start planning your return visit.
Recommended for Italian because: Osteria Trulli is the only authentic Pugliese eatery in the Chicago area and it's worth the drive. It's independently owned and a real find.
Jacky's expert tip: You'll think your GPS is wonky taking you through a residential street. Trust it because the restaurant is tucked behind Hintz Rd.