Bella NottePeople generally seem to love gargantuan portions (for the value), but when the heaps actually taste good, it’s a win-win. Couples here linger over decent bottles of wine and specialties like garlicky housemade sausage links with blistered bell peppers, fresh cavatelli and rapini swimming in white-wine garlic-butter sauce, roasted chicken oreganato and a juicy, seared New York strip with sweet and vinegary peppers. The bar and handful of café tables up front are perfect for a stop-in drink or dessert. 1374 W Grand Ave (312-733-5136). Lunch (Mon–Fri), dinner. Average main course: $20.
Club LagoIf you thought a chimney crashing through the ceiling and obliterating the kitchen below could keep Club Lago down, then you have obviously never been to Club Lago. Despite a fairly recent renovation, the place looks exactly the same as always, and is even staffed by many of the same servers who have been there for decades. So follow suit and regress to old habits: massive portions of lasagna, soft roast beef on white bread, carafes of watery Chianti and—this is crucial—some pasta with Lago’s meat sauce. 331 W Superior St (312-951-2849). Lunch, dinner (closed Sun). Average main course: $11.
Club LuckyThe nearby condo dwellers with kids in tow may be a different crowd than the Polish regulars who once frequented the joint post-Prohibition, but the owners have gone out of their way to restore the original cocktail-culture look of the ’50s. The place is always packed, thanks to a dependable, old-school, family-style Italian menu with standouts like grilled calamari, chicken Vesuvio, and escarole with sausage and beans. Kidphobic? Go late for the lounge vibe of Sinatra standards and signature martinis. 1824 W Wabansia Ave (773-227-2300). Brunch (Sun), lunch (Mon–Fri), dinner. Average main course: $16.
RoSal’sTypically, we’d tell the server to save the speech, but here, it’s somehow still charming when the bubbly girl “from da neighborhood” explains how the namesake owners Roseanne and Salvatore came to open their Little Italy spot. Cozy cuteness aside, the food’s among the best on the Taylor Street strip. Start with the lightly charred but tender grilled calamari; get a pasta course of big, fat garlicky shrimp tossed with shells and broccoli; and go for the veal saltimbocca with a side of spinach for the main event. 1154 W Taylor St (312-243-2357). Dinner (closed Sun). Average main course: $18.
Sabatino’sA dark and cozy date-friendly ambiance, seasoned servers and old-school Italian dishes—what’s not to like about this place? Couples should snag a booth, the perfect spot for sipping a well-priced bottle of Chianti and kicking the night off with the signature cheesy garlic bread. Shrimp De Jonghe is fresh (and garlicky as hell), ricotta-filled manicotti and gnocchi in meat sauce won’t disappoint, and the extra-thick New York strip is seasoned only with salt and pepper before hitting the grill for a spot-on medium-rare. Drinkers should skip dessert and finish the night at the adjacent bar. 4441 W Irving Park Rd (773-283-8331). Lunch (Sun–Fri), dinner. Average main course: $15.
Tufano’s Vernon Park TapThis old-school Italian joint is holding strong in its ever-changing ’hood. The chalkboard menu rarely changes, and regulars never even glance at it before ordering the house specialty: Lemon chicken Vesuvio packs a fistful of garlic, and the roasted, citrus-spritzed chicken is among the best around. After a couple of bites, you’ll get caught up in the tradition of the place, enough to overlook iceberg salads, standard pastas and carafes of jug wine. 1073 W Vernon Park Pl (312-733-3393). Lunch (Tue–Fri), dinner (closed Mon). Average main course: $14.