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Illustration: Jennifer Thermes

Taste Quest Harlem Avenue

Rev up with a cuppa real-deal espresso before hitting all the stops along the best Italian food-and-drink strip in town.


The Italian neighborhood in Chicagoland most likely to make your stomach happy is nowhere near Little Italy. It isn’t any closer to the Heart of Italy neighborhood, either—in fact, it technically isn’t even in Chicago. But out on the northern stretch of Harlem Avenue (the 7200 West block), where many Italians settled after World War II, there lies a head-spinning array of delicious delis, bakeries and cafés, where hearing Italian spoken is as common as getting a great espresso. (Harlem neatly bifurcates the towns of Montclare and Elmwood Park: The former is on the east side, the latter the west.) Start at North Avenue and head north, but first empty your trunk to make room for the culinary booty.

The original Harlem location of 1Caputo’s Grocery(2560 N Harlem Ave, 708-453-0155) is legendary in Chicago: Angelo Caputo started it as a streetside stand a half century ago. The stand later became  a supermarket, but its products never disappoint: housemade ricotta, mozzarella and sausage; a superb meat and seafood selection; superfresh vegetables—all for bewilderingly little money. The store carries many mainstream products, too, which is convenient, but only a fool comes to Caputo’s to buy OJ. The smart shoppers are here to load up on olive oil, canned tomato and pasta.

Across the street is 2Caffe Italia(2625 N Harlem Ave, 773-889-0455), where you can energize yourself for a Caputo’s run with a beautifully pulled espresso or calm down afterward with a digestivo. It may be dark and vaguely shady—as shady as a bar with a foosball table can be, that is—but don’t be intimidated: The staff is amiable. And when the weather warms up, the owner begins churning out his prized housemade gelato. 

A brief detour west on Belmont Avenue will bring you to 3Nottoli and Son (7652 W Belmont Ave, 773-589-1010) and its impressive collection of porcine figurines. Sausage makers since 1950, the Nottolis owe a lot to the pig: In the summer (high sausage season) the shop stuffs up to 3,000 pounds daily in every Italian sausage iteration. The shop also has tubs of Nottoli-brand giardiniera, delicious sandwiches (try the Dante’s Inferno) and a wall of glossies from owner George Nottoli’s side career as a professional wrestler. His name? Vito “Two Fingers” Fontaine.

Back on Harlem, 4Riviera Italian Foods(3220 N Harlem Ave, 773-637-4252) is a family-run grocery that will win your heart within minutes. Warm and extraordinarily accommodating, the store’s famous for its glorious cured meat case and the made-to-order subs on which those meats are piled. Between its deli selections (meat, cheese, marinated vegetables) and a freezer full of premade pastas and sauces, Riviera can make your fridge look like it belongs on a food-porn set.

There are never enough Sicilian bakeries in anyone’s life, and the delightful 5Palermo Bakery(3317 N Harlem Ave, 773-777-5957) satisfies both savory and sweet appetites. Palermo has terrific sheet pizza and a child’s wonderland of cookies and cakes, including hilarious Russian doll–like cannoli cakes (many little cannolis inside a single steroidal cannoli).

Despite the wall-to-wall mafia-kitsch, 6Caponie’s(3350 N Harlem Ave, 773-804-9024) managed to make room for a wood-burning oven, and although multiple Sopranos posters are rarely an auspicious sign for a restaurant, the crispy, thin-crust pizza (“the pizza you can’t refuse”) here is excellent. Get a bocconcini (baby mozzarella balls) and please, for the sake of the pun-tired waitresses, don’t be a wiseguy.

A few shops north is 7Gino’s Italian Imports(3422 N Harlem Ave, 773-745-8310), yet another outstanding Italian deli. Such routine quality can be exhausting, and after Caputo’s and Riviera, stopping at Gino’s may seem absurd. But the selection and service here is as good or better than anywhere else: On a recent visit, an unfailingly knowledgeable employee walked the length of the case, offering us samples of anything we wanted. And only Gino’s has 8Pasta Fresh(3418 N Harlem Ave, 773-745-5888) next door, where the owners are so confident of their shop’s name they installed a glass window so customers can watch the pasta being made. Don’t leave without tortellini in hand. 

At the northern end of the strip is 9Bar Café San Francesco(3815 N Harlem Ave, 773-283-1117), which is perhaps better recognized by the command emblazoned on its Italian flag–colored awning: taste our cappuccino. Like Caffe Italia, San Francesco does morning and night duty—both close at 2am—and it feels genuine: low on looks but high on atmosphere. In any case, concentrate on your cup—the espresso’s marvelous and the milk for the cappuccinos, which have a divine sugar-and-cocoa crust, is frothed with the care of someone who’s preserving a dying craft.

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