From uber-cheap to uber-luxe, we’re laying out the best spots to hit up in Chicago for your first time in the city. We’re talking classic local spots with signature items like a Chicago dog dragged through the garden and towering deli sandwiches made with the best corned beef and pastrami on Earth. Whether you’re balling on a budget or looking to splurge, these restaurants will give you a true taste of Chicago.
Superdawg Drive-In
Norwood Park
Why you’re here: Superdawg, a Chicago staple since 1948, delivers a unique drive-in experience for enjoying a classic Chicago dog.
What you’re ordering: The Superdawg of course (delivered via a car hop!). Once you open the iconic Superdawg box you’ll find a 100% pure beef hot dog loaded with yellow mustard, pickled tomatoes, a kosher pickle spear, chopped onions and hot peppers, all cushioned on a bed of crinkle fries. Its signature beefy snap makes it stand out from other Chitown dogs. Other must-try items include the Whoopskidawg, their take on a polish sausage served on an onion roll with grilled onions and a pickle spear. If you’re really going big, add an order of onion chips and an ultra-thick Supershake.
6363 N. Milwaukee Ave. (map)
Kasama
West Town
Why you’re here: As the only Filipino tasting menu in the country, Michelin-starred Kasama is truly worth a visit.
What you’re ordering: Chefs Genie Kwon and Timothy Flores have garnered attention for both their casual daytime menu and their evening tasting menu. By day, grab some of their wildly popular baked goods like the ube and huckleberry basque cake or black truffle croissant, and the longanisa, egg and cheese breakfast sandwich. By night, snag a reservation for the 13-course Filipino-inspired tasting menu featuring upscale takes on adobo and lumpia.
1001 Winchester Ave. (map)
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Milly’s Pizza in the Pan
Uptown
Why you’re here: Sure, there may be more well-known pizza joints in this town, but Milly’s is a non-traditional option churning out some of the best pies you’ll find. The ghost-kitchen-turned-storefront is also in the heart of Uptown’s Little Vietnam making it a worthwhile excursion from downtown.
What you’re ordering: This is not your traditional Chicago deep dish. It’s better. Chef Robert Malecki’s thick, caramelized crusts are loaded with umami-rich tomato sauce and dollops of your favorite toppings. Try the “Craigslist.org” topped with peppadew peppers, sausage, mushrooms, red onions, tomatoes, spinach and ricotta. We recommend ordering ahead as pizzas are limited each day.
1005 W. Argyle St. (map)
Monteverde
West Loop
Why you’re here: The West Loop is Chicago’s dining neighborhood and Monteverde has been a staple.
What you’re ordering: Top Chef alum Sarah Grueneberg’s menu of Italian fare is flawlessly executed. Begin your journey with the burrata e ham featuring rosemary tigelle AKA soft pillows used as a carrier for prosciutto, burrata and seasonal mostarda. Monteverde was menuing cacio e pepe well before it was trendy, and its version that uses whey from ricotta and toothy bucatini is mindblowing. Larger plates like the ragu alla napoletana with pork osso bucco, soppressata meatballs, Italian sausage, fusilli and escarole are crowd and stomach pleasers, while a butterscotch budino with buttered pecan toffee makes for a sweet ending.
1020 W. Madison St. (map)
Manny’s Deli
South Loop
Why you’re here: Chicago’s favorite deli has been an institution since 1942, serving up breakfast, lunch and dinner deli classics.
What you’re ordering: Manny’s is set up cafeteria style so grab a tray and head down the line. Start with a piping hot bowl of matzo ball soup and pair it with a piled-high corned beef or pastrami sandwich on rye. If you really want to go big, opt for The Chazzer with corned beef, pastrami, cole slaw, muenster and thousand island dressing on the side. Plop a big fat potato pancake on your plate and wash it all down with a Dr. Brown’s soda.
1141 S. Jefferson St. (map)
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