Illustration by Hawk Krall
This is part of a series of late-night city guides supported by The Sexton Irish Whiskey and inspired by the The Sexton Midnight Club, an intimate event series for chefs who want to eat and drink well after a late-night shift.There are people who claim you shouldn't eat right before bed. With all due respect, these people are wrong. As far as after-hours decisions go, doubling down on fat and carbs before heading home is, quite frankly, one of the tamest decisions you could make. And bonus: if you’ve been drinking, they might even help you feel better the next morning. Given that, your midnight snack is practically a matter of national health and safety. And though Chicago isn’t open all hours the way New York or LA is, you can still find many late-night, gut-filling options in The City of Big Shoulders.
1846 W Division St, Chicago, IL 60622
(773) 276-7422Machine caters to a wide range of needs with its imaginative menu, which changes three times a day. But the real stars are the Willy Wonka-like cocktails, where among their deep bench you can expect flowers frozen in ice, a crème brûlée-inspired sip complete with caramelized top, and puns like the “Alco-Hall & Oats.”Jim's Original
1250 S Union Ave, Chicago, IL 60607
(312) 733-7820The spicy, ultra-garlicky Polish sausages at Jim’s Original—established in 1939—are part of the city’s DNA. It also doesn’t hurt that the Union Street stand (original in spirit but not location) was the first to serve them with hot peppers, mustard, and grilled onions. Vegetarians need not apply.Moneygun
660 W. Lake St, Chicago, IL 6066
(312) 600-0600A West Loop speakeasy serving classic cocktails and small plates right up until closing time. Come for the old-fashioned, stay for the disco fries. The owners insist it’s “just a bar,” which, given its general lack of pretension is exactly the selling point.JoJo's Milk Bar
23 W Hubbard St, Chicago, IL 60654
(312) 624-8963Yes, there are sandwiches, soups, and salads at JoJo’s Milk Bar, but if you’re not ordering a side of fries solely as a vehicle to get a milkshake into your face, you’re doing it wrong. JoJo’s six signature shakes (with names like “Cheery Poppins” and “Girl Scout”) are an exercise in childlike giddiness, but for an extra six dollars, you can turn them into dessert cocktails.White Palace Grill
1159 S Canal St, Chicago, IL 60607
(312) 939-7167An old-school diner (open since 1939 to be exact) with endless egg options, plus chicken and waffles and an ever-rotating, seriously meat-heavy slate of blue plate specials.Chicagos Pizza
Lakewood/Ravenswood/Old IrvingAnother in Chicago’s pizza heritage sites. Skip most of the pages in their ridiculously opulent menu (five pages of tiny type), and head directly to the titular dish, served stuffed, thin crust, deep dish, or as a calzone.High Five Ramen
112 N Green St, Chicago, IL
(312) 344-1749A ramen-only basement joint with a single 15-seat counter and only a handful of options (pork, seafood, and vegetarian.) For best results, go spicy—The “High Five” has melt-your-face-off levels of kick). Too hot? Don’t freak: their Coconut Painkiller Cocktail is there to put out the fire.Pequod's Pizza
2207 N Clybourn Ave, Chicago, IL 60614
(773) 327-1512A Chicago deep-dish education—just as long as you’re ready to wait for it. (They don’t take reservations, but you can call ahead to be added to the priority seating list upon arrival.) The secret here is the caramelized cheese crust, where a thin layer of mozzarella sits between the chewy dough and the cast-iron pot, blackened into a layer of crispy sweetness. You can satisfy your late-night cravings there until 2 a.m.San Soo Gab San
5247 N Western Ave, Chicago, IL 60625
(773) 334-1589A Koreatown BBQ joint with large piles of meat and a well-stocked bar. They also offer a robust menu of kimchi-laced carbs which soak up whatever you've been out doing: the kimchi fried rice and kimchi pancakes are both top-notch.Lawrence's Fish & Shrimp
3242 W 87th St, Chicago, IL 60652
(312) 796-5048Lawrence’s is where you go when you want fish, shrimp, chicken, and assorted seafood battered and fried to golden, heart-stopping perfection. Hit the Canal street location, where all this—plus slaws and sides (yes, there’s a green salad; no, we don’t know why)—can be yours 24 hours a day.Owen & Engine
2700 N Western Ave, Chicago, IL 60647
(773) 235-2930If traditional English pub food is your comfort of choice, then Owen & Engine’s got you. The Logan Square eatery does the traditionally heavy, carb-filled, meat-centric food proud, with recognizable canon entries (including scotch eggs, Cornish pasties, and fish and chips) and what many consider Chicago’s best burger.
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Machine
1846 W Division St, Chicago, IL 60622
(773) 276-7422Machine caters to a wide range of needs with its imaginative menu, which changes three times a day. But the real stars are the Willy Wonka-like cocktails, where among their deep bench you can expect flowers frozen in ice, a crème brûlée-inspired sip complete with caramelized top, and puns like the “Alco-Hall & Oats.”Jim's Original
1250 S Union Ave, Chicago, IL 60607
(312) 733-7820The spicy, ultra-garlicky Polish sausages at Jim’s Original—established in 1939—are part of the city’s DNA. It also doesn’t hurt that the Union Street stand (original in spirit but not location) was the first to serve them with hot peppers, mustard, and grilled onions. Vegetarians need not apply.Moneygun
660 W. Lake St, Chicago, IL 6066
(312) 600-0600A West Loop speakeasy serving classic cocktails and small plates right up until closing time. Come for the old-fashioned, stay for the disco fries. The owners insist it’s “just a bar,” which, given its general lack of pretension is exactly the selling point.JoJo's Milk Bar
23 W Hubbard St, Chicago, IL 60654
(312) 624-8963Yes, there are sandwiches, soups, and salads at JoJo’s Milk Bar, but if you’re not ordering a side of fries solely as a vehicle to get a milkshake into your face, you’re doing it wrong. JoJo’s six signature shakes (with names like “Cheery Poppins” and “Girl Scout”) are an exercise in childlike giddiness, but for an extra six dollars, you can turn them into dessert cocktails.
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1159 S Canal St, Chicago, IL 60607
(312) 939-7167An old-school diner (open since 1939 to be exact) with endless egg options, plus chicken and waffles and an ever-rotating, seriously meat-heavy slate of blue plate specials.Chicagos Pizza
Lakewood/Ravenswood/Old IrvingAnother in Chicago’s pizza heritage sites. Skip most of the pages in their ridiculously opulent menu (five pages of tiny type), and head directly to the titular dish, served stuffed, thin crust, deep dish, or as a calzone.High Five Ramen
112 N Green St, Chicago, IL
(312) 344-1749A ramen-only basement joint with a single 15-seat counter and only a handful of options (pork, seafood, and vegetarian.) For best results, go spicy—The “High Five” has melt-your-face-off levels of kick). Too hot? Don’t freak: their Coconut Painkiller Cocktail is there to put out the fire.Pequod's Pizza
2207 N Clybourn Ave, Chicago, IL 60614
(773) 327-1512A Chicago deep-dish education—just as long as you’re ready to wait for it. (They don’t take reservations, but you can call ahead to be added to the priority seating list upon arrival.) The secret here is the caramelized cheese crust, where a thin layer of mozzarella sits between the chewy dough and the cast-iron pot, blackened into a layer of crispy sweetness. You can satisfy your late-night cravings there until 2 a.m.San Soo Gab San
5247 N Western Ave, Chicago, IL 60625
(773) 334-1589
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3242 W 87th St, Chicago, IL 60652
(312) 796-5048Lawrence’s is where you go when you want fish, shrimp, chicken, and assorted seafood battered and fried to golden, heart-stopping perfection. Hit the Canal street location, where all this—plus slaws and sides (yes, there’s a green salad; no, we don’t know why)—can be yours 24 hours a day.Owen & Engine
2700 N Western Ave, Chicago, IL 60647
(773) 235-2930If traditional English pub food is your comfort of choice, then Owen & Engine’s got you. The Logan Square eatery does the traditionally heavy, carb-filled, meat-centric food proud, with recognizable canon entries (including scotch eggs, Cornish pasties, and fish and chips) and what many consider Chicago’s best burger.