The Resy Guide to Chicago’s New Old-School Restaurants

Charlie Martin’s is an ode to 1950s and 1960s-era Hollywood supper clubs. Named after director Charlie Martin, this spot is all about the white tablecloths, the pintucked banquettes, the long bustling bar, and jazz-era music. Grab an ice-cold Charlie’s martini (a surprising twist on the classic with Sipsmith gin, St. George basil eau de vie, Lillet blanc, and olive oil). Then dig into a wedge salad or roasted bone marrow, then steak frites, miso cod kicked up with a sprinkle of togarashi, or a delicate whole roasted dover sole with brown butter. And if you’re really going to go all old Hollywood, caviar service would be a fine idea.

You may not have realized you were nostalgic for the 1920s, but walk into Armitage Alehouse, with its cozy fireplace, pineapple-carved lamps, tasselled pendants hanging along the bar, burgundy booths, and ornate details just about everywhere (peacock wallpaper!), and you’ll begin to wonder if it’s the decade you’ve been longing for, after all. And that’s before you’ve even tried a drink, from an obscure vintage cocktail to a British-style ale, or something from the Anglo-Indian menu, like ultra crisp fish and chips or a buttery steak and ale pie. Want to make sure you’ll always have a seat? Here are a few insider tips.  

You can’t get much more old-school  than one of the oldest Italian-American restaurants in the city. Founded in 1927 by Italian immigrant Alfredo Capitanini, The Village is a storied Chicago spot—rumored to be the birthplace of Chicago’s first chicken Vesuvio and a favorite of Al Capone’s, though we can’t confirm or deny either. Tuck into a red banquette among the frescos and twinkle lights for comforting pastina in chicken broth, the house specialty lasagna, veal cutlet parmigiana, or “The Tony” sandwich, which brings a little bit of Chicago pride to this iconic menu: thinly sliced ribeye, arugula, red onions, tomatoes, and giardiniera aioli.

While it is decidedly new, there’s a lot that feels delightfully old-school about Dimmi Dimmi. There’s the decor inspired by “a vivacious art-loving nonna,” including red-and-white checked booths and rich green pintucked bar stools. And then there’s the menu from chef Matt Eckfeld. While he came up in New York’s upscale  Carbone and Torrisi, he’s having more fun here, with extra crunchy and stretchy mozzarella sticks, focaccia served in a blazing hot cast iron skillet, cavatelli bolognese, and very good tavern-style pies. Everything is made from scratch and endlessly comforting.

For an old-school French bistro feel (think curved bistro chairs, white tablecloths, Parisian charm that never seems to go out of style), there’s Petit Pomeroy from Ballyhoo Hospitality. Like its sister restaurant Pomeroy in Winnetka, Petit Pomeroy is laser-focused on the French classics: good fresh baguettes with butter to start, onion soup gratinee, and escargots a la bourguignonne. There’s dreamy mushroom risotto and a bouillabaisse, a trout amandine, and a perfectly roasted half chicken—everything you’d expect at a traditional bistro. Perhaps the only snippet of Americana is the Buck Russell red velvet cake with cream cheese icing for dessert: A sweet little quirk to make us Chicagoans feel like kids again. We’ll take it.

While some old-school Italian joints keep things traditional, Void is taking some risks. Sure, the setup has some familiar trappings of the genre : the gilded frames, the Tiffany-inspired pendants, the overall vintagey feel that makes you want to just hang around with a drink in hand. But the menu, from hospitality vets Pat Ray, Dani Kaplan, and Tyler Hudec, brings some pizzazz: There are the “Spaghetti Uh-Ohs” (poured tableside from a can, just like your childhood favorite) in housemade vodka sauce. There are agnolotti made from Korean sweet potatoes with kimchi butter and stretchy mozzarella. And the chicken marsala is double-fried, a la Korean fried chicken. Come here for an innovative blend of old-school meets new.

There is something inherently nostalgic about sitting down to a big plate of barbecue (preferably with the sun on your face). At Babygold Barbecue, chef and pitmaster Steve Domanik hits all of our pleasure receptors with baby back ribs, brisket, pork belly, and  cheddar-bay hush puppies. What makes Babygold an even greater nod to old-school Americana is its location right next to legendary music venue Fitzgerald’s. If you’re lucky, your trip will line up with a music festival or live show, so you can chow down  and tap your toes all at the same time.

Ample portions of Italian-American classics (from linguine with clams to eight-layer eggplant parmesan), “giant” signature martinis, and friendly service have made Club Lucky a Bucktown stalwart since 1990. Inspired by supper clubs of the 1940s, the decor here will take you back in time: the cocktail lounge has cherry red bar stools and banquettes for sipping a Vesper Lynd (from Casino Royale, of course), while the dining room is packed with tables and booths for a hustle and bustle that’s fun and exuberant — perfect for gathering with friends who also enjoy a throwback paired with excellent food and drink. 

Margie’s Candies has been delivering sweets and sundaes to Chicago kids and adults for over 100 years. Step into this confectioner’s paradise and you’ll know just from the sweet caramel smell alone that you’re in good hands. From jumbo ice cream sundaes with exceptionally good hot fudge drizzled from a gravy boat and extra thick malts to phosphates (now those are old-school) to lots of homemade candies (like turtles, truffles, and honeycomb chips), there’s something for everyone here. While Margie’s has done some recent collabs with new-age brands like Kith, the focus still seems to be on keeping things classic. (Whew!)

No reservations, more info here.