Top Spots for Steakhouse Comfort Foods in Chicago

From bacon-topped salads to decadent desserts, these are Chicago’s can’t-miss steakhouse comforts.

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All year round, from patio season to those cozy fireplace months, Chicago’s steakhouses are among the best spots for comfort. But it’s when the temperatures plummet that those comfort foods really soar. Sure, burly and hulking servings of steak are inherently comforting in and of themselves, but don’t forget about all those decadent appetizers and side dishes that really make a wintry meal sing. From fried ravioli to baked clams, here are Chicago’s best steakhouse comfort foods.

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Benny’s Chop House: From Parmesan-dusted truffle fries and sous vide short ribs to bacon-dressed iceberg wedge salads, Benny’s Chop House has no shortage of upscale comfort food. The steakhouse features plenty of more health-conscious dishes, too, but let’s be honest: this is the time of year when you just want Brussels sprouts with bacon vinaigrette, mac & cheese and oysters Rockefeller.

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Prime & Provisions: At this slick Loop newcomer, beef isn’t the only indulgent protein. In fact, the steakhouse shares the spotlight quite handily with other crowd-pleasers like fried chicken with chile-bourbon-maple drizzle, thick-cut slabs of bacon accented with dark chocolate, black pepper, and maple syrup, and steaming bowls of thick New England-style clam chowder.

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Erie Cafe: This riverside oasis in River North is chock full of hearty comfort fare, starting with appetizers like piping hot fried ravioli with blue cheese to platters of Italian sausage with grilled peppers. Don’t overlook the steamy mussels immersed in tangy, bubbling marinara.

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Chicago Chop House: This venerable oldie has amassed legendary status for good reason, and it’s not just because the steaks are stellar. It’s also because the calamari gets the crispy tempura treatment, the baked oysters Rockefeller get a smattering of smoked bacon, and the creamy lobster bisque comes outfitted with chopped lobster morsels and an enriching drizzle of white truffle oil.

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Mastro’s Steakhouse: When it comes time for dessert, one of the best destinations in town is Mastro’s Steakhouse. This protein palace is just as satisfying on the sweet side as it is on the savory, thanks to its lengthy list of standout desserts. These include the restaurant’s signature warm butter cake (’nuff said), cheesecake, chocolate pudding cake, key lime pie, gelato, cherry crisp, profiteroles, and many more.

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Joe’s Seafood, Prime Steak & Stone Crab: Another apt locale for desserts is this downtown stunner. The perpetually packed restaurant is known just as much for its pie and sundaes as it is for its seafood and steaks. Case in point: the killer banana cream pie with Foster sauce, the chocolate marquis pie with mocha creme anglaise, the peanut butter pie with hot fudge, and even the all-too-rare Boston cream pie, which is technically a cake but no less wonderful.