Chicago’s food scene goes way beyond deep dish pizza and hot dogs. The Windy City’s sandwich shops have been stuffing bread with delicious fillings for generations, creating cult followings and neighborhood traditions. From Italian beef dripping with jus to mile-high pastrami creations, these sandwich institutions have earned their legendary status through consistency, quality, and that special something you can’t find anywhere else.
1. Portillo’s: The Beef King
Started as a humble hot dog stand in 1963, Portillo’s has grown into Chicago’s sandwich royalty while keeping its soul intact. Their Italian beef sandwich – thinly sliced roast beef soaked in savory gravy and stuffed into French bread – might be the most iconic sandwich in the entire city.
What makes Portillo’s special isn’t just the food but the experience. The retro décor, the organized chaos of the ordering system, and the lightning-fast service all add to the charm. Locals argue passionately about whether to order it dry, wet, or dipped, with sweet peppers or hot giardiniera.
Though now expanded beyond Chicago, the original locations maintain their authentic feel. For the full experience, pair your beef with their chocolate cake shake – a milkshake with an entire slice of chocolate cake blended in.
2. Manny’s Cafeteria & Delicatessen: South Side Institution
Walking into Manny’s feels like stepping back in time to 1942 when this Jewish deli first opened its doors. Fourth-generation family owners still slice the corned beef and pastrami by hand, piling it impossibly high between slices of rye bread.
Presidents, mayors, and celebrities line up alongside regular Chicagoans in this cafeteria-style landmark. The walls decorated with decades of political memorabilia tell stories of deals made and broken over potato pancakes and matzo ball soup.
How do they manage to keep their sandwiches so consistently perfect? The secret might be in their stubborn refusal to change with the times. While other delis have modernized, Manny’s sticks to what works – quality ingredients, generous portions, and zero pretension. Their corned beef is so tender it practically melts before you can finish your first bite.
3. J.P. Graziano Grocery: Little Italy’s Treasure
Hidden among the rapidly gentrifying streets of what was once Chicago’s Little Italy, J.P. Graziano stands as a defiant reminder of the neighborhood’s roots. Since 1937, this Italian grocery store has transformed into sandwich heaven while maintaining its old-world charm.
Their signature Italian sub – loaded with premium imported meats, provolone, and dressed with house-made truffle-mustard vinaigrette – has foodies making pilgrimages from across the city. Family recipes passed down through four generations ensure authentic flavors you simply can’t replicate.
Though the surrounding area has changed dramatically, stepping into Graziano’s transports you to another era. The shelves stocked with imported Italian specialties, the smell of freshly sliced prosciutto, and the friendly banter between staff and regulars create an atmosphere as satisfying as the sandwiches themselves.
4. Al’s Beef: The Original Italian Beef Master
If sandwiches were royalty, Al’s Italian beef would wear the crown in Chicago, Illinois. Founded in 1938 by Al Ferrari during the Great Depression, this sandwich shop pioneered what would become one of Chicago’s signature dishes – the Italian beef sandwich.
What’s their magic formula? Paper-thin slices of seasoned roast beef soaked in a secret-recipe gravy, stuffed into a sturdy Italian roll that somehow maintains its integrity despite being saturated with beefy goodness. The Taylor Street location remains the mecca for purists seeking the most authentic experience.
Watching the staff at Al’s is like witnessing a choreographed dance – they work with rhythmic precision, dipping sandwiches with practiced flicks of the wrist. When they ask if you want it “wet” or “dipped,” the correct answer is always “dipped.” Just bring extra napkins and don’t wear your fancy clothes!
5. Ricobene’s: Home of the Breaded Steak
While tourists flock to the more famous sandwich spots, South Side natives know Ricobene’s breaded steak sandwich deserves its own place in the culinary hall of fame. USA Today once crowned it the “Best Sandwich in America,” and locals didn’t even blink – they already knew.
Imagine thinly pounded steak, breaded and fried until golden, then smothered in homemade marinara sauce and stuffed into an Italian roll. Topped with melted mozzarella and sweet or hot peppers, this beast requires both hands and total concentration to eat.
Founded in 1946, Ricobene’s started as a small street stand and grew into a Chicago institution without losing its neighborhood charm. The original 26th Street location still attracts multi-generational families who’ve been eating these sandwiches for decades. Their late-night hours have saved many hungry night owls from despair.
6. Nini’s Deli: The Comeback Kid
Before controversy temporarily shuttered this beloved spot in 2020, Nini’s had earned a cult following for its unique Cuban-meets-Mexican-meets-Lebanese sandwich creations. Now reopened and under new management, the deli continues its tradition of culinary fusion that reflects Chicago’s melting pot identity.
Their signature Cubano – pressed to crispy perfection and stuffed with slow-roasted pork shoulder – remains the star attraction. However, adventurous eaters gravitate toward their Puebla sandwich, which incorporates unexpected ingredients like pickled jalapeños and chipotle mayo into traditional Lebanese flavors.
Though small in size, Nini’s punches far above its weight class. The tiny storefront in Noble Square often has lines stretching down the block, especially on weekends. Many customers develop an almost religious devotion to specific sandwiches, returning weekly for their fix.
7. Bari: Old-School Italian Sub Specialists
Hidden in plain sight on Grand Avenue since 1973, Bari remains one of Chicago’s most cherished Italian groceries and sandwich counters. Unlike trendier spots with Instagram-worthy interiors, Bari lets its sandwiches do all the talking.
Their Italian sub has achieved legendary status not just in Chicago, but throughout Illinois, thanks to a perfect balance of imported meats, sharp provolone, and their house giardiniera that delivers just the right amount of heat. The bread – crusty on the outside, pillowy inside – comes from D’Amato’s Bakery next door, creating a hyperlocal food experience you can’t replicate.
Though the shop itself is tiny, with just a few employees working behind the counter, their efficiency is remarkable. Regulars know to order by number and step aside as the sandwich makers work their magic. Many old-timers who’ve moved to the suburbs still make special trips back to the neighborhood just for a Bari sub.
8. Mr. Beef: River North’s Working-Class Hero
While River North has transformed into an upscale dining district, Mr. Beef stubbornly maintains its no-frills approach to sandwich perfection. Made famous by celebrity endorsements (including a loving portrayal in “The Bear” TV series), this tiny beef stand has served the same perfect Italian beef sandwich since 1979.
Unlike some competitors who’ve expanded into chains, Mr. Beef remains fiercely independent with just this single location. The interior – with its cramped counter space, photos of celebrity visitors, and worn-in charm – feels like a time capsule from a grittier Chicago era.
What makes their beef special? Perhaps it’s the perfectly seasoned gravy or the way they steam the beef to juicy perfection before serving. Maybe it’s the crusty-yet-soft bread that somehow holds together despite being drenched in jus. Whatever the secret, this sandwich represents Chicago’s blue-collar roots in every delicious bite.
9. Tempesta Market: The New-School Legend
Though newer to Chicago’s sandwich scene (opened in 2018), Tempesta Market has quickly earned legendary status through its uncompromising approach to quality. Founded by the Calabrese family behind ‘Nduja Artisans, this West Town market combines old-world Italian techniques with modern culinary creativity.
Their Dante sandwich – loaded with six different house-cured meats, provolone, and truffle honey – represents a masterclass in flavor layering. Every ingredient is made in-house or sourced from premium producers, creating sandwiches that justify their higher price point.
Unlike many old-school Chicago sandwich spots, Tempesta embraces a bright, modern aesthetic while maintaining deep respect for traditional methods. The market section sells their house-cured meats and imported specialties, allowing customers to recreate some magic at home. For serious food lovers, their charcuterie boards and prepared foods make this a one-stop culinary destination.
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