24-hour Chicago restaurants
The room is big and wide-open, and yet thanks to the homey design (the mismatched chairs; the collection of plates on the wall), this diner feels more like a small, charming café. But don’t let that fool you: The menu has all the diner staples it should have, from plate-sized omelettes to hearty Monte Cristo sandwiches to the signature: oven-baked pancakes almost the size of the room.
The large crowd at the counter of this bare-bones Indo-Pak spot seems chaotic, but the diners are really just waiting for their postmeal chai. So push your way through, and order a bowl of delicious dal, loaded with bay leaves and chili peppers. Ask for the chili chicken and spoon the greasy, delicious, fiery red chunks onto the dense paratha bread. No matter what you order, you’ll get your money’s worth; most things here cost only about four bucks.
Does this diner even have locks on its doors? It certainly doesn't need them: The colorful, retro spot feeds hungry (and, often, drunk) Wicker Parkers 24 hours a day, 365 days a year. Like many great diners, you can order breakfast, from french toast to chilaquiles, at any time. But the extensive menu has everything else you can imagine, too: salads, burgers, steaks, wraps, sandwiches, pie, cake and much more.
This mini-chain (there are three scattered throughout the South Side) focuses on two major food groups: ice cream and doughnuts. The savory food is perfectly solid—tuna melts could feed three; burgers are charred on the outside and juicy within—but the real deal is what comes next. For most people, that’s a doughnut topped with ice cream. But for our money, an apple fritter does the job better.
There is a bevy of 24-hour greasy-spoon diners in this city, but none of them offer anything as curious as Jeri’s “jailhouse special,” a plate of fried bologna, eggs, hash browns and toast. Kind of makes you wonder what Jeri was up to before the grill, doesn’t it? Get there before 2pm for the biscuits and gravy; the rest of the cheap eats are served all day and include fries and patty melts.
A little walk-up shack on the UIC Campus with no seating, Jim's Original doesn't look like much. But a solid rendition of a Vienna beef Chicago-style dog with fries sets you back just $2.85, and the grilled onions are a nice touch. Open 24 hours a day, Jim's Original is just as good for lunch as late night munchies.
You can smell the unmistakable aroma of sautéing onions at this 24-hour diner from across the street, so you better believe each menu item is imbued with that sweet fragrance. That's definitely true of the bone-in pork chop sandwich, which is, well, exactly what it sounds like: a grilled pork chop sandwich with its bone very much still attached, placed on a bun, squirted with some mustard, and finished with a hefty pile of those onions. It's a messy, full-flavored lunch, and, as long as you eat around the bone, totally worth the hassle.
Though this tiny 24-hour shack with a three-seater counter serves only two flavors of soft serve—vanilla and chocolate—it’s the 54 flavors of milkshakes that draw out folks at all hours. By throwing candy, cookies and flavored syrups into the blender, they create flavors like “baboon” (chocolate and banana), Oreo and strawberry shortcake—thick shakes that pair well with an order of chili-cheese fries and a burger at 4am.
The first thing to know before heading for this Chinatown gem is that it’s not the giant Three Happiness on the corner of Wentworth Avenue, and the difference is monumental. Ignore the far-from-spotless decor (or lack thereof) and skip the so-so appetizers in favor of black pepper beef with rice noodles (ordered “crispy”), crispy salt-and-pepper shrimp and Cantonese-style crispy-skin chicken.