16 Old-School Restaurants in Chicago for a Classic Night Out

For classic interiors at Chicago institutions and bucket list meals, look no further than these Windy City standbys.

Superdawg Drive-In
Photo courtesy of Superdawg Drive-In

Once upon a time, in those Medieval days before Michelin Stars and James Beard galas, Chicago was stereotyped as a meat-and-potatoes town, infamous for its stockyards (thanks, Upton Sinclair) and enough meat-processing plants to earn it the eerie nickname of “hog butcher to the world.” Things have evolved significantly in the past hundred or so years, though. Sure, the Midwestern metropolis still loves its meat and potatoes, but sometimes they come in the form of hot dogs with crinkle-cut fries, or Reuben sandwiches with latkes, or a 38-ounce dry-aged tomahawk rib-eye with rosemary-roasted spuds.

Meaty or not, many enduring restaurants have evolved with Chicago as its morphed into the epicurean epicenter it is today. The city now boasts mind-melting tasting menus and celebrity chefs, but it’s these timeworn classics that help keep the city rooted, and Chicagoans have plenty of room in their hearts for an old-school steakhouse or diner just as much as they do for the hot new thing.

Through the pandemic, which saw the shuttering of beloved institutions like Dinkel’s Bakery, Yoshi’s, and Everest, it’s heightened the appreciation for these venerable standbys, and what they mean to the city’s food scene. From fine dining to casual neighborhood sub shops, and cinnamon rolls to salad bars, the old guard is rich with as much perseverance as nostalgia, and they’re as crucial to the city’s dining DNA as the fine dining icon serving translucent pumpkin pie. Let’s raise an Old Fashioned to these seminal old-school restaurants in Chicago.

Gene & Georgetti
Gene & Georgetti | Photo by Soda Fountain Photography

Gene & Georgetti

River North
$$$$

In a city with a surplus of steakhouses, Gene & Georgetti reigns as the OG. Opened in 1941, making it the oldest steakhouse in town, the debonair River North restaurant was the vision of pals Gene Michelotti and Alfredo Federighi (whose nickname, Georgetti, was apparently a better phonetic fit), this beefy bastion has remained a generational go-to for its seasoned steaks and equally seasoned service. Although Gene and Georgetti have passed, their legacy remains—including a dining room that feels utterly preserved in time, with buttoned-up power lunchers and more framed black-and-white photos than most history museums. Even as snazzy newfangled steakhouses pop up throughout the city, guests return to the charm of Gene & Georgetti time and again, for its superlative steaks, its veal saltimbocca, its shrimp de Jonghe, and its singular setting as the kind of place where you might bump elbows with politicians or athletes, or get your shoulder lovingly smacked by a jovial manager.
How to book: Walk-ins are always accepted. The restaurant also offers takeout and delivery via Toast.

Available for Reservations

Borinquen Lounge

North Center
$$$$

From hot dogs to Italian beef, Chicago lays claim to plenty of iconic foods, but one such nosh that deserves higher billing is the almighty—and wildly underrated—jibarito. It’s an unabashedly garlicky sandwich made with two slices of fried plantains in lieu of bread, years before that whole “let’s use other foods instead of bread for sandwiches” craze became a thing. Invented by Juan Figueroa in 1996, the novelty came to him as an homage to his upbringing on Puerto Rico, utilizing familiar flavors he grew up eating to achieve maximum comfort. Named jibarito as a nod to the jibaros (aka farmers) on the island, his original recipe featured a heap of thinly shaved steak, onions, tomatoes, shredded lettuce, cheese, and aïoli, all smooshed between two crispy plantains slathered in garlic butter. It’s like a Caribbean cheesesteak, basically. The OG sandwich, which has gone on to inspire a slew of jibarito concepts all over the city, was initially served out of a sparse cafeteria-style space in Humboldt Park, but has since moved to larger digs in North Center. Now open for nearly 20 years, Borinquen Lounge feels like a tavern you might stumble into in San Juan, featuring tropical touches like neon palm trees and Puerto Rican flags in every nook and cranny, where the star attraction is still well worth the garlic breath.
How to book: Walk-ins are always easy and convenient, and takeout orders can be placed by calling 773-442-8001.

Available for Delivery/Takeout

Svea

Andersonville
$$$$

Despite the fact that Chicago has a low-key huge Swedish population, Scandinavian businesses have been a dwindling breed in the Second City. One such stalwart that stands resolute, though, is Svea. In operation since 1972, this pint-sized Swedish diner has been a comfort food cornerstone in Andersonville, the north side neighborhood most known for its Scandinavian culture (see also glögg-chugging Simon’s Tavern down the block). Despite the closure of institutions around it, like nearby Swedish Bakery after 88 years, this frills-free, cash-only charmer is still going strong with its meatballs, pickled herring, limpa, salt pork, and lingonberry rice pudding, served with a smile in a cute space with enough bright blues and yellows to do the Swedish flag proud.
How to book: Walk-ins are welcome.

Chicago Diner

Northalsted
$$$$

In 1983, when Chicago was sill typified as a meat-and-potatoes town, one funky diner decided to zig against the zag—aka eschew meat for a 100% vegetarian menu in the heart of the clubby gayborhood. Founded by spouses Mickey Hornick and Jo A. Kaucher, who went vegetarian on a dare when she was 19, the notion of a meat-free diner was audacious. So much so that it was difficult to get a loan from business lenders who deemed it too wild and risky. The duo changed public perception with their emphasis on hearty and familiar food—e.g. hulking Reuben sandwiches, country-fried “steak,” milkshakes, and gyros—in a space that felt just as familiar as a comfy roadside diner. There just happens to be more pride flags and seitan than your typical diner. The recipe proved a successful one, spawning another location in hipster-packed Logan Square, and the original outpost on North Halsted still commands a queue for some of the most inventive and decadent comfort food around, all of which just happens to be meat-free.
How to order: Pickup and delivery orders can be placed directly through the website.

Available for Reservations

Ann Sather

Lakeview
$$$$

Many restaurants have a particular renown for a single menu item. At Outback Steakhouse, it’s the Bloomin’ Onion; at Chicken Guy!, it’s Donkey Sauce; and at Chicago’s Ann Sather, it’s all about the cinnamon rolls. These ooey-gooey pastries are so indulgent and fragrant that they make Cinnabon smell bland. Doughy and fluffy, rolled in butter and cinnamon-sugar and liberally doused in treacly icing, these things aren’t for the faint of heart—but these sugar bombs are a rite of passage as one of Chicago’s most everlasting confections. The Swedish-influenced restaurant has been churning ‘em out—along with lingonberry-clad Swedish pancakes and a bevy of egg dishes—since 1945, when the restaurant’s namesake set up shop in a defunct storefront on Belmont Avenue, with the intent to create the type of homey dream diner where customers could feel warm and welcome, if not spiraling into a sugar coma. Her dream came true in the form of a sunny, cottage-like diner hinged on from-scratch cooking and time-tested recipes, including those cinnamon rolls with a cult-like following. Sather passed away in 1997, but her recipes and hospitality live on—including at a few newer locations on the north side.
How to book: Available for dine-in on a first come, first served basis (keep in mind that the wait can be arduous on weekends), and delivery orders can be placed via UberEats.

Available for Delivery/Takeout
Calumet Fisheries
Photo courtesy of Calumet Fisheries

Calumet Fisheries

South Deering
$$$$

Open for near a century, and run by the same family since 1948, it doesn’t get much more quintessential old-school than Calumet Fisheries. As casual and frills-free as they come, this teeny fish shack on the edge of the Calumet River is a true throwback to yesteryear—to a time when boats would chug by and the area’s large Scandinavian population would reap their rewards in the form of smoked salmon, shrimp, trout, and sable. Although South Deering’s demographics have changed, the timeless craving for fish has not. To this day, the cash-only shanty still stocks its counters with fish and seafood that undergoes a tedious process of marinating overnight, baking, and hanging to smoke over wood for several hours in an attached smokehouse. Devoid of indoor seating, this is the kind of place you come to stock up on smoked fish (and a side of macaroni salad) and get down ’n’ dirty on the hood of your car, while overlooking the adjoining 95th Street bridge made famous by the car-jumping scene in The Blues Brothers.
How to book: Delivery is not available, nor are reservations, but feel free to visit the smoke shack to dine outside, or call 773-933-9855 to place an advanced order.

Superdawg Drive-In

Norwood Park
$$$$

Before Sonic popularized the concept of the fast-food drive-in in 1953, there was Superdawg, rising like a neon beacon over Chicago’s far northwest side. Since 1948, the retro restaurant has been an Americana pastime for Chicagoans and tourists alike, especially those looking for something a little more unique and a little less touristy than your typical downtown fodder. Founded by Maurie and Flaurie (aka Florence, again with the phonetics) Berman, Superdawg is in a league of its own when it comes to Chicago hot dogs. Unlike most Chicago-style dogs, these snappy bad boys come with onions, sport peppers, mustard, a pickle, and most originally, pickled green tomato for extra zing. It’s all bundled up neatly in a colorful, comic book-esque box alongside a bed of hot crinkle-cut fries. The drive-in format emerged out of convenience, as a way for cars to park by electronic speakers and place orders for carhops to deliver right to your window. Nowadays, Superdawg has another location in Wheeling and a few newer menu items, but the ritual of eating its namesake menu in your car remains as tried-and-true a Chicago pastime as any.
How to book: Delivery isn’t available, nor are advanced orders. Just park your car, roll down your window, and order away.

RJ Grunts

Lincoln Park
$$$$

We’re not saying that Ruby Tuesday was directly inspired by R.J. Grunts to make salad bars a thing, but we’re also not not saying that. After all, the salad-centric chain opened just a year after this Lincoln Park institution did in 1971, establishing itself as the first of many (so many!) restaurants for Chicago’s largest hospitality group, Lettuce Entertain You Enterprises, and making a name for itself with its first-of-its-kind salad bar in the city. Long before the group dominated the city’s dining scene with the likes of Three Dots and a Dash, Aba, and Hub 51, it all started with this cozy, art-filled nook of a restaurant, ingratiating itself as a neighborhood fixture with its something-for-everyone menu (e.g. buffalo chicken, milkshakes, pot roast, and good old fashioned cheeseburgers.). The vision of Rich Melman and his first business partner, Jerry Orzoff, the restaurant has remained a Lincoln Park staple, possibly due to the fact that the salad bar, with its 50+ ingredient options and 9,986,548,936 possible combinations, demands a revisit.
How to book: Reservations are available on Tock, or customers can place both delivery and carryout orders directly though the website.

Candlelite

Candlelite

Rogers Park
$$$$

This may come as a shock, but most Chicagoans don’t get their pizza fix at Pizzeria Uno downtown. In fact, many locals don’t even consider deep-dish to be the definitional “Chicago-style,” but rather a gluttonous casserole whose cravings come around as infrequently as Halley’s Comet. Rather, tavern-style (aka “party-style”) pizza is widely heralded as the true Chicago-style, a far thinner pie with a crisp crust strewn with cheese and, unlike deep-dish, a smattering of evenly dispersed toppings that shows restraint. Sliced into small squares, it’s become the go-to pizza for pairing with beer at the corner bar. Among Chicago’s myriad pizza pioneers in this genre, Candlelite ranks among the best. Opened in 1950, flickering like a neon candle over far North Western Avenue, you won’t find any deep-dish here. Rather, it’s all about the cracker-thin pizza at this familial eatery decked out in brick walls, snug booths, and sports memorabilia. Over the past 70 or so years, it’s evolved from a higher-end date spot (hence the name, Candlelite) to a beer-swilling dive, before settling into its current family-friendly fomat for locals, with an expanded menu that offers burgers, sandwiches, and poutine tots alongside those pepperoni-clad beauties.
How to book: Dine at Candlelite on a first come, first served basis, or place an order for delivery or pickup directly through their website. Candlelite also has a fast-casual stall in Time Out Market Chicago, which offers delivery through DoorDash and UberEats.

Available for Delivery/Takeout

Lou Mitchell's

West Loop
$$$$

Long before a sea of skyscrapers enveloped it, Lou Mitchell’s was the quintessential road trip-ready diner. Between its hearty all-American breakfast platters—including six-egg (!) omelets fluffier than meringue, stuffed with the likes of ham, smoked salmon, and even apples and cottage cheese—and the fact that the restaurant is located at the beginning of Route 66, this was the type of diner you’d come to fuel up and ensure you won’t be hungry for about a week. Nowadays, amidst the urban hustle and bustle, folks are still fueling up for other reasons. Namely, an undying obsession with silver dollar pancakes, eggs Benedict, thick wedges of French toast, and the self-proclaimed “World’s Finest Coffee,” all doled out by lovably surly servers. After opening in 1923 and with nearly a century under its belt, the restaurant still clamors with delighted customers, and it still gives out free donut holes to all guests (plus free Milk Duds to women and children).
How to book: Dine-in is available on a first come, first served basis, and customers can place pickup orders through ChowNow.

Manny's Restaurant
Photo by courtesy Manny's

Manny's Restaurant

South Loop
$$$$

While Chicago may not have the famous deli lore of, say, a New York, at least we’ve got Manny’s. And that’s pretty special. Easily one of the most essential dining experiences in the city, this South Loop staple has been churning out latkes, matzo ball soup, and mile-high Reuben sandwiches since 1964. Since its inception, this sprawling cafeteria has been family-run (founded by Jack Raskin, who named it after his son Emanuel), with time-tested recipes that have passed through subsequent generations. And that renown endures for customers new and old, who load up their trays with beef brisket, corned beef, and pastrami sandwiches so hilariously huge that they’re really more like mountains of shaved meat with a bread garnish. In true cafeteria form, the menu is dizzying, with a rotating roster of sides, entrees, and sweets, like rice pudding, meatloaf, mac & cheese, and knishes, just to scratch the surface.
How to book: In addition to dine-in on a first come, first served basis, Manny’s offers both delivery and takeout via Toast.

Available for Delivery/Takeout

Birrieria Zaragoza

Archer Heights
$$$$

Despite the fact that this family-run taqueria has only been in business since 2007, which might feel downright precious compared to some of the older relics on this list, the story of Birrieria Zaragoza extends far deeper. Founded by patriarch Juan Zaragoza, the casual concept is an homage to the food he grew up eating in Jalisco—and the food he craved while raising a family in his adopted hometown of Chicago. Entirely self-taught in the kitchen, routinely traveling home to Jalisco to stock up on real-deal ingredients and learn the tricks of the taqueria trade, Zaragoza succeeded in bringing a deeply authentic, earnest taste of Jalisco to Chicago’s southwest side. Goat birria is the restaurant’s bread and butter, made with goat butchered in-house, steamed for hours until meltingly tender, marinated in earthy mole, and roasted to impart those flavors into the succulent meat. The go-to order is a bowl of birria in warm, heady consommé, a soothing balm for the most bracing of Chicago winters. Served with fresh tortillas and add-ons like raw onions, lime, and fresh cilantro, it’s one of the city’s simplest pleasures—and one of its greatest.
How to book: In addition to dining on-site, Birrieria Zaragoza offers pickup and delivery through UberEats.

Available for Delivery/Takeout
Geja's Cafe
Geja's Cafe | Photo courtesy of Geja's Cafe

Geja's Cafe

Lincoln Park
$$$$

True love never fades. Which might explain why this uber-romantic restaurant remains a requisite for Valentine’s Day and proposals—there’s just something so enchanting about sharing bowls of molten cheese and chocolate with a loved one. Geja’s Cafe has been wooing couples from its wine cellar-esque basement in Lincoln Park since 1965, and in those ensuing decades, it’s seen more engagements than any other restaurant in town—a recent tally clocked it as the site of 141,638 first dates and 16,616 engagements, proving the universal pangs of bubbling crocks of Gruyere fondue, skewers of beef tenderloin, and classical guitarists roving the candlelit basement, like something out of a Disney movie. While fondue has largely fallen by the wayside in America, Geja’s Cafe keeps the flame alive with an undeniable formula for swoon-worthy crock pots in a singularly dreamy space.
How to book: Walk-ins are available. Geja’s also offers carryout directly through its website, though you’re on your own with the guitar.

Available for Reservations
Roeser's Bakery
Photo courtesy of Roeser's Bakery

Roeser's Bakery

Humboldt Park
$$$$

Open since 1911, Humboldt Park’s Roeser’s Bakery holds the distinction as Chicago’s oldest family-run bakery. What it lacks in bells and whistles, this charmingly vintage bakery more than makes up in classic American desserts—the kind of cloyingly delicious white cake frosting, iced sugar cookies, and glistening strawberry tarts that feel like a dying breed in this modern world of Cronut NFTs and fried ice cream pie. Like a living time capsule, Roeser’s maintains its charm in its third generation of ownership (now run by John Roeser III), and continues to delight families looking for their next sugar fix.
How to book: The bakery is always open for walk-ins on a first come, first served basis, and custom cake orders can be placed through their website.

A lot can change in 85 years. Whereas once, you’d be able to take your horse and buggy to shop for Italian sundries in the cobblestone-clad enclave that’s now the West Loop, nowadays you might find yourself eating a sub on a sidewalk table under the shadows of the Nobu Hotel. After Vincenzo “J.P.” Graziano opened J.P. Graziano Grocery as an Italian wholesale market in 1937, which feels like 500 years ago based on the rapid-fire development in the buzzy ‘hood, it’s grown into one of the city’s most beloved sandwich shops. It’s the type of rare gem that perseveres no matter what, and the fact that this old-school market and sandwich stop still exists, on one of the most coveted stretches of restaurant real estate in the nation, says a lot about the business, its loyal customers, and the fourth-generation owners who keep it thriving. Today, Jim Graziano maintains the inherent charm of this authentic Italian market, while also implementing well-received additions, like offering more imported Italian grocery items, crafting habit-forming cannoli, and serving made-to-order sandwiches, stuffed to the gills with provolone, hot sopressata, prosciutto di Parma, and truffle mustard. It’s the kind of heartwarming place where the passion is palpable—in every sandwich and on every shelf—and one can only hope to keep scarfing sandwiches here for the next 85 years.
How to book: Takeout orders can be placed on the company’s website, or you can call (312) 666-4587 to order ahead as well.

Italian Village
Photo courtesy of Italian Village

Well before haute takes on Italian food became the “in” cuisine in Chicago, this colossus of a downtown restaurant was simmering red sauce, rolling meatballs, and pouring glasses of Chianti to the brim. The oldest Italian restaurant in the city, which has since expanded and ballooned to become a veritable Disney World of pasta and meat sauce, Italian Village first stated out as simply The Village in the heart of the Loop in 1927. Florence-born Alfredo Capitanini opened the restaurant as a culinary ode to various regions in Italy, spotlighting essential eats like chicken Vesuvio, eggplant Parmigiana, and veal saltimbocca. What really left an impression, though, was the immersive and magical decor, including fixtures reminiscent of a countryside villa and a ceiling mural designed to replicate a starlit Tuscan sky. It was apparently so charming that Al Capone was said to be a fan. Then, as Capitaninis kids joined the business in 1955, the family expanded into the basement with another Italian concept, La Cantina, where steaks and chops are the bill of fare in an intimate space designed like a private wine cellar. The Village expanded yet again with The Florentine Room (now called Vivere) on the ground floor in 1961, with an emphasis on more contemporary cookery in a vast and luminous space that looks like a palace out of Aladdin. No matter which enchanting room you visit, Italian Village is the kind of timeless treasure that reminds you of the everlasting comfort of soulful Italian food.
How to order: Carryout is available via Toast.

Available for Delivery/Takeout
Available for Reservations
Matt Kirouac is a recent transplant to Oklahoma City after two and a half years of RV living, Matt Kirouac is a travel writer working on a memoir about the epic ups and downs from life on the road as a gay couple—and the lessons learned along the way. Follow him on IG @mattkirouacofficial.