15 Must-Try Sandwiches That Are Purely Chicago
Chicago may be famous for its deep-dish pizza and hot dogs, but its sandwich game is just as bold, messy, and unforgettable.
From beef dripping in jus to spicy giardiniera explosions, every bite tells a story of neighborhoods, tradition, and unapologetic flavor.
These sandwiches aren’t trying to impress anyone outside the city limits. They’re proudly, stubbornly Chicago.
Grab extra napkins, loosen that belt a notch, and get ready to meet the city between two slices of bread.
1. Italian Beef
Thinly sliced roast beef soaked in herb-infused gravy creates Chicago’s most iconic sandwich.
Born during the Great Depression when meat had to stretch further, this juicy masterpiece comes on a sturdy French roll. Order it ‘wet’ (dipped in jus), ‘sweet’ (with bell peppers), or ‘hot’ (with giardiniera).
Locals debate whether Al’s, Johnnie’s, or Portillo’s serves the best version, but everyone agrees: eating this drippy delight without wearing half of it is impossible.
2. Maxwell Street Polish
Grilled or fried kielbasa sausage smothered with caramelized onions and yellow mustard on a poppy seed bun creates sandwich magic.
Originally sold from pushcarts in the Maxwell Street Market, this Polish-American creation reflects Chicago’s Eastern European heritage. The secret lies in the perfect char on both sausage and onions.
Many vendors closed when the original market was demolished, but Jim’s Original and Express Grill still serve authentic versions, keeping this street food tradition alive 24 hours a day.
3. Pork Chop Sandwich
Bone-in pork chops fried golden brown and tucked into a soft bun create a uniquely challenging eating experience. Found primarily on Chicago’s South Side, this sandwich requires strategic biting around the bone.
Seasoned simply with salt and pepper, the meat’s natural flavor shines through. Maxwell Street vendors pioneered this working-class favorite decades ago.
The bone serves as both a flavor enhancer and a convenient handle, making this sandwich a delicious puzzle worth solving.
4. The Freddy
Ground beef patties smashed thin, grilled with onions pressed directly into the meat, and topped with American cheese create sandwich perfection.
Freddy’s in Cicero invented this beauty, which lands somewhere between a burger and a patty melt. The magic happens when beef juices caramelize with the onions.
Served on grilled rye bread with optional giardiniera, this sandwich demonstrates how Chicago transforms humble ingredients into something extraordinary.
Locals know to ask for extra napkins when tackling this gloriously messy creation.
5. Jibarito
Flattened, fried green plantains replace bread in this Puerto Rican-Chicago innovation.
Created in Humboldt Park during the 1990s, the jibarito features steak, lettuce, tomato, cheese, and garlic mayo between crispy plantain ‘buns.’
The contrasting textures make each bite exciting – crunchy plantains against tender meat.
Juan Figueroa at Borinquen Restaurant claims to have invented it, naming it after a diminutive term for Puerto Rican people. This neighborhood specialty has now spread citywide, becoming a true Chicago original.
6. Gym Shoe (Jim Shoe)
Corned beef, roast beef, AND gyro meat piled together create this South Side sensation.
Nobody’s quite sure about the name origin – perhaps from ‘gyro’ mispronounced, or maybe because it’s as substantial as a shoe.
Topped with lettuce, tomato, mayo, mustard, tzatziki, and giardiniera on a sub roll, it’s a multicultural marvel.
This sandwich represents Chicago’s melting pot perfectly, combining Italian, Greek, and Jewish deli traditions. Found primarily in South Side sub shops, it remains a local secret many tourists never discover.
7. Mother-in-Law Sandwich
A tamale nestled in a hot dog bun and smothered with chili creates this quirky South Side classic. Legend claims the name comes from its reputation for giving heartburn – just like dealing with your mother-in-law!
Fat Johnnie’s Famous Red Hots still serves authentic versions of this Depression-era creation. Usually topped with mustard, onions, and sport peppers for extra kick.
This unusual combo shows how Chicago’s diverse cultural influences created entirely new food traditions you won’t find elsewhere.
8. Pepper and Egg Sandwich
Scrambled eggs with sautéed green peppers on Italian bread create this humble masterpiece.
Popular during Lent when Catholics abstained from meat, it became a year-round favorite in Italian-American neighborhoods.
The beauty lies in its simplicity – just eggs, peppers, olive oil, and sometimes a sprinkle of Parmesan.
Old-school Italian delis across the city still prepare these to order. Locals know adding giardiniera gives it the perfect Chicago kick, transforming this modest sandwich into something special.
9. Italian Sausage Sandwich
Fennel-laced pork sausage grilled to perfection and nestled in Italian bread creates this aromatic delight. Chicago’s version distinguishes itself with the sweet-hot combo of sautéed bell peppers and giardiniera.
Every neighborhood Italian joint has their own version, but the best come from places that make sausage in-house.
Found at street festivals, ballparks, and family restaurants citywide. The sandwich represents Chicago’s large Italian-American community that shaped the city’s food landscape for generations.
10. Beef and Sausage Combo Sandwich
Why choose between Italian beef and Italian sausage when you can have both? This magnificent marriage layers thinly sliced beef over a grilled sausage in a single French roll.
Commonly called ‘combo’ for short, it delivers the perfect balance of textures – tender beef with snappy sausage.
True Chicago sandwich enthusiasts know to order it ‘wet’ with both sweet and hot peppers. This indulgent creation embodies Chicago’s go-big-or-go-home food philosophy.
11. Chicago-Style Hot Dog
Vienna Beef frank ‘dragged through the garden’ with seven specific toppings creates Chicago’s most famous handheld meal.
The ritual combination includes yellow mustard, neon green relish, chopped onions, tomato wedges, pickle spear, sport peppers, and celery salt on a poppy seed bun.
Never, ever ask for ketchup unless you want to be identified as a tourist! This fully-loaded creation emerged during the Depression when vendors needed to offer a complete meal in one package.
Gene & Jude’s, Superdawg, and Portillo’s serve some of the city’s most authentic versions.
12. Pizza Puff
Deep-fried flour tortilla filled with mozzarella, tomato sauce, and usually sausage creates this portable pizza alternative.
Invented by Chicago’s Iltaco Foods in the 1970s, these savory pockets became staples at hot dog stands citywide.
The outside gets crispy while the inside becomes molten lava hot – careful with that first bite!
While technically not a sandwich by strict definition, Chicagoans consider it one, and no local would question its inclusion on this list. Perfect late-night food after hitting the bars.
13. Shrimp DeJonghe Sandwich
Chicago’s classic shrimp DeJonghe casserole reimagined as a sandwich creates buttery, garlicky perfection.
The original dish – shrimp baked with garlic-herb breadcrumbs – was invented at DeJonghe’s Hotel and Restaurant in the early 1900s.
Enterprising sandwich shops adapted it by piling the shrimp mixture onto French bread. Found primarily in old-school seafood restaurants and delis near Lake Michigan.
This sandwich showcases Chicago’s historic connection to fine dining while making it accessible in portable form.
14. Chicago-Style Relish Sandwich
Electric green sweet pickle relish becomes the star ingredient in this quirky Chicago creation.
Built on a sesame bun with mustard, onions, and sometimes a smear of cream cheese, it celebrates the city’s famous condiment.
The neon-bright relish gets its distinctive color from blue dye added to yellow relish – a Chicago tradition dating back decades.
Found primarily at old-school delis and specialty sandwich shops. This simple sandwich proves that sometimes the supporting players deserve their own spotlight.
15. The Classic Chicago Club Sandwich
Stacked three layers high and held together with those fancy toothpicks, the Chicago Club Sandwich takes the traditional club to spectacular heights.
Local delis and diners put their Windy City spin on this classic by using thicker-cut bacon from Chicago’s historic meatpacking tradition.
The bread? Always toasted to golden perfection. What makes the Chicago version special is the addition of avocado and a signature garlic aioli that replaces standard mayo.
Some spots even add a sprinkle of giardiniera for that distinctly Chicago kick.