Chicago Dog
Classic Beef Hotdog
Chili Cheese Dog All Beef
Maxwell Street Polish Sausage
Chicago Italian Beef
Chicago Style Combo
Bbq Beef
Cheesy Beef
Homemade Italian Sausage
Bbq Pulled Pork Sandwich
Maxwell Street Bone In Pork Chop Sandwich
Fried Pork Tenderloin Sandwich
Fried Bologna Sandwich-Thick Cut
Crinkle Cut Fries
Cheese Fries
Chili Cheese Fries
Chicago Beef Tamale
Pizza Snack Bites
Chicago Pizza Puff
Greek Lemon Fries
Loaded Bacon Fries
Garlic Ghost Pepper Fries
Loaded Bbq Pulled Pork Fries
Bowl Of Chili
Garden Salad
Classic Chicago Gyro
Gyro Platter
Traditional Greek Salad
Crinkle Cut Fries
Cheese Fries
Chili Cheese Fries
Chicago Beef Tamale
Chicago Pizza Puff
Loaded Bacon Fries
Garlic Ghost Pepper Fries
Loaded Bbq Pulled Pork Fries
Bowl Of Chili
Big Herm's Chicago Style Food Menu brings a little taste of the Windy City down to 3946 Pine Island Rd in Matlacha, and the vibe hits you before you even start eating. The menu leans into bold, comforting flavors, and it’s the kind of place where you find yourself scanning the options twice just to make sure you don’t miss anything. As you read through it, you’ll notice how each item feels familiar but still exciting, from stacked sandwiches to hearty classics that make you slow down for a moment.
What really stands out is how effortlessly the dishes pair that laid-back Chicago attitude with Florida’s easygoing energy. It all fits together in a way that makes choosing what to order surprisingly fun, especially if you’re the type who enjoys discovering new favorites. And while the portions are generous, it’s the inviting mix of flavor and character that makes the whole menu worth exploring.