Chicago’s food scene is famous for its Michelin-starred restaurants and deep-dish pizza, but a more casual culinary craze has taken over the city: the sandwich. From celebrity chefs to beloved local institutions, everyone is getting in on the act, crafting everything from luxurious lobster rolls to classic Italian beef. If you’re looking to sink your teeth into the best bread-and-filling combinations the Windy City has to offer, you’ve come to the right place. Here is your guide to the most delicious and memorable sandwiches in Chicago.
The Ultimate Guide to Chicago’s Most Delicious Sandwiches
Cafecito’s Killer Cubano: A Taste of Havana in Chicago
Adjacent to the snazzy J. Ira & Nicki Harris Family Hostel, this cute Latin counter offers some of the most delicious pressed sandwiches in town. The Cubano is a standout, featuring ham, roast pork, and Swiss cheese. The perfect vinegary tang comes from mustard and pickles, all pressed between fresh Cuban bread until it’s warm and wonderfully crisp-chewy.
The Gage’s Roasted Woodland Mushroom Sandwich: A Vegetarian Delight
Chef Dirk Flanigan, renowned for his game dishes, showcases his expertise with this vegetarian masterpiece. The roasted woodland mushroom sandwich is packed with firm, smoky mushrooms, watercress, and tangy pecorino. A schmear of earthy truffle aioli completes this satisfying and meaty sandwich, proving that vegetarian options can be just as decadent.
Portillo’s Italian Beef: An Iconic Chicago Classic
Portillo’s is a local institution known for many things, but its Italian beef sandwich is in a league of its own. It’s a symphony of paper-thin slices of marinated roast beef and hot or sweet peppers stuffed into a chewy Italian roll. For the full experience, order it “wet”—dipped in rich beef jus for a deliciously sloppy and memorable bite.
Xoco’s Pibil Torta: A Mexican Culinary Masterpiece
As expected from Frontera Grill maestro Rick Bayless, his quick-serve spot Xoco delivers on flavor. The pibil torta is a palate-thrilling sandwich featuring wood-roasted suckling pig, achiote, black beans, and pickled onion. The caliente habanero salsa adds a fiery kick to the crisp-chewy roll, making it a true Mexican culinary masterpiece.
Ba Le’s Ba Le Special: The Perfect Banh Mi
The key to a great banh mi is the bread, and Ba Le excels with its crisp, chewy, flaky, and super-fresh baguettes. The Ba Le Special is a top-notch creation filled with savory pâté, ham, headcheese, pork roll, mayonnaise, and house-pickled daikon and carrot. Slices of jalapeño and fresh cilantro add the final, perfect touch.
Hopleaf’s Pan-Fried “CB&J”: A Gourmet Twist on a Classic
Hopleaf elevates the humble peanut butter and jelly sandwich to a new level. Their intensely rich pan-fried “CB&J” features house-made cashew butter, fig jam, and creamy Morbier cheese. This decadent creation is served with a side of über-rich Stilton mac and cheese, making for an unforgettable and luxurious meal.
All Too Well’s Refined Delicatessen
All Too Well is a celebrated neighborhood delicatessen that offers an exciting menu of high-quality, made-to-order sandwiches. Their focus on fresh, local ingredients and classic techniques has made them a favorite among Chicagoans looking for a refined yet comforting meal.
Al’s Beef’s Classic Italian Beef
Al’s Beef is a quintessential Chicago experience, famous for its no-frills approach to the classic Italian beef sandwich. Known for its perfectly seasoned, thinly sliced beef and simple, yet delicious, preparation, it’s a must-visit for anyone seeking an authentic taste of the city’s sandwich heritage.
