Must-try Dishes
Deep Dish Pizza - Thick crust pizza filled with cheese, toppings, and a hearty tomato sauce on top. Locals tend to order it for dinner, often sharing a pie amongst friends after a night out.
Italian Beef Sandwich - Giardiniera Sandwich - Sliced beef roasted in seasoned broth, served on a crispy roll with pickled vegetables. It's a go-to street food for lunch, and many wrongly ask for “extra peppers” when they mean the giardiniera.
Chicago Hot Dog - All-beef frankfurter in a poppy seed bun topped with mustard, onions, neon relish, and a pickle spear. Typically enjoyed as casual street food, it's best eaten during a summer festival for that true Chicago vibe.
Chicago Style Ribs - Tender spare ribs slathered in a tangy barbecue sauce, grilled to perfection. It’s a beloved dinner option at family gatherings, often accompanied by coleslaw and cornbread.
Portillo's Chopped Salad - Chopped Salad - A hearty mix of greens, chicken, cheese, and a house vinaigrette, offering a surprising crunch and flavor blend. Commonly enjoyed for lunch, especially during those hot summer afternoons when you want something light yet filling.
Shakshuka - Shakshouka (breakfast dish) - Poached eggs in a spicy tomato and pepper sauce, seasoned with herbs. This energizing dish is popular for brunch, best enjoyed with crusty bread to soak up the sauce.
Seasonal Corn on the Cob - Elote - Grilled corn slathered with mayo, cheese, and chili powder, offering a delightful combination of sweet and savory. Locals savor it during summer festivals at street fairs, often lingering for a second ear!
By the way, when ordering, toss in “light on the giardiniera” for a milder kick, a common mistake tourists make.
Desserts & Drinks
Hot Chocolate - Drinking Chocolate (rich cocoa blend) - Deeply flavored cacao mixed with steamed milk and topped with whipped cream or marshmallows. Perfect for chilly winter afternoons, it's often enjoyed at local specialty shops after a long day exploring the city.
Malört - Malört (herbal liqueur) - A bitter, spirituous drink with a distinct wormwood flavor that’s unique to Chicago. Locals typically shoot it, especially during late nights at dive bars, and it’s often accompanied by a friendly grimace. By the way, be ready for a taste experience that many swear by, while others merely endure!
Italian Ice - Granita (icy dessert) - A refreshing frozen treat made from flavored water, sugar, and fruit, perfect for hot summer days. Typically found at street vendors during festivals, it’s served in a cup and is an absolute must for cooling off.
Paczkis - Paczki (filled pastries) - Delicious, fluffy, and jelly-filled pastries traditionally served on Fat Tuesday. These indulgent treats are best enjoyed at local bakeries and often sell out quickly, so get them early if you want to savor the flavors—especially the lemon filling, which is a local favorite!
Cold Brew - Cold Brew Coffee (smooth, chilled coffee) - Cold coffee steeped with coarsely ground beans for hours, served over ice and often garnished with a splash of cream. Perfect for summer mornings, it’s a staple at local cafés, and many locals enjoy it alongside a fresh pastry for breakfast—just remember to specify the milk options, as they can vary!
