Ada’s Famous Deli If the mark of a good Jewish deli is the schmaltz, Ada’s is in good shape: Circles of oil glimmer on top of the matzo-ball soup, and the peppery hot pastrami is rich with soft fat. And it gets even better: Latkes, appropriately greasy yet crisp, can be substituted for rye in the pastrami sandwich (a worthy option if your health can handle it). Plus, it has decent bagels for schmearing thick layers of cream cheese. The only area that isn’t so schmaltzy? The service, which, in a rejection of true deli culture, is downright sweet. 14 S Wabash Ave (312-214-4282). El: Blue, Red to Monroe; Brown Green, Orange, Pink, Purple (rush hrs) to Madison. Bus: 2, 10, 151. $2 soup with the purchase of any sandwich.
Birchwood Kitchen The Pastoral vets behind this cozy BYOB know the secret to making a sandwich more than just a sandwich: sourcing. That’s why a brunch plate of smoked salmon features creamy Zingerman’s goat cheese, and why they chose Mint Creek Farms lamb to slice onto a baguette and get dipped in a sweet jus. And that’s why they often stuff their sandwiches with housemade pickles. To pair with that sandwich: a discounted soup of the day. 2211 W North Ave (773-276-2100). El: Blue to Damen. Bus: 49, 50, 56, 72. $2.50 soup with purchase of any sandwich.
Eleven City Diner Owner Brad Rubin scoured the country to research this Jewish deli/diner. His pastrami is tender, fatty, full of flavor, and tastes even better with a side of Bubbie’s chicken soup. The milkshakes are thick and oversized, the matzo balls are enormous, and the brisket is good enough that any grandmother would want to claim it. Does it hold a candle to other Jewish spots in the country? Well, Rubin definitely holds his own as the host, giving this place enough character to become a fixture in its own right. 1112 S Wabash Ave (312-212-1112). El: Green, Orange, Red to Roosevelt. Bus: 1, 3, 4, 12. Half-sandwich and soup: $10.99.
Hannah’s Bretzel What could possibly get you to patronize a place where a sandwich, salad and cookie will set you back, oh, about $18? Here are just a few ideas: soft yet crusty housemade “bretzel” (read: pretzel) rolls (avoid the anemic whole-wheat version). Uncommon marriages of fresh ingredients, such as watercress-cheddar–mango chutney and serrano ham–manchego-fennel-fig. Assurances that most (but not all) ingredients are organic. An entire wall dedicated to artisanal chocolate bars. A design aesthetic that conjures trendy Europe. And a soup-and-sandwich lunch special that—to buck this restaurant’s pricey trend—sets you back just under $10. 131 S Dearborn St (312-269-5500). El: Blue, Red to Monroe. Half-sandwich and soup: $9.37.
My Pie Pizza/Li'l Guys Deli A good deli and a good pizza place—does a neighborhood need anything else? By serving deep-dish with a rich crust and chunky, slightly spicy sauce, owner Rich Aronson is continuing a family tradition (his father opened the first My Pie in 1971). The deli, on the other hand, was his idea. House-cured corned beef, fresh-fruit smoothies and fudgy brownies are three reasons he may have another tradition on his hands. 2010 N Damen Ave (773-394-6900). El: Blue to Western. Bus: 50, 73. “Daddy Pack” of sandwich, soup and drink: $13.
Zaleski & Horvath Market Cafe A couple of Hyde Park veterans (the former owners of Istria Café) and a sandwich maker from the suburbs joined forces for this casual but high-quality deli/grocery store. Crowds (a mix of nerdy professor types and nerdier students) gather at the counter for Spanish jamon sandwiches with quince paste and panini that press farmstead cheese and ham between pretzel bread. The oatmeal–chocolate-chip cookies are a hot item, too—though not nearly as hot as a seat at one of the few tables. 1323 E 57th St (773-538-7372). Elec Main to 55th-56th-57th St. Bus: 170, 171, 172. Half-sandwich and soup: $7.50.