Embarking on Route 66 is an adventure filled with roadside nostalgia, quirky attractions, and miles of open road. But before you roll onto the Mother Road, there’s no better place to fuel up than Chicago—a city celebrated for its rich culinary tapestry and iconic dishes. Chicago isn’t just a starting point for Route 66, it’s a destination where every bite tells a story. From deep-dish pizza that redefines the pie to hot dogs so sacred they come with their own set of rules (spoiler: don’t ask for ketchup), Chicago’s food scene is as diverse and bold as the city itself.
Each dish offers a taste of Chicago’s history and character, from the Polish immigrants who popularized the Maxwell Street Polish to the Italian-Americans who perfected the art of the Italian beef sandwich. And don’t forget the dessert; the city boasts its own brownie origin story and a rainbow-colored ice cream cone that’s a treat for both your eyes and taste buds.
This guide will take you on a culinary tour through 15 must-try Chicago classics before you hit the open road. Whether you’re grabbing a bite at an old-school diner or experiencing fine dining at a legendary steakhouse, these dishes will leave you with a full stomach and a deeper appreciation for Chicago’s vibrant food culture. So, loosen your belt, grab a fork, and prepare to eat your way through the Windy City—it’s the perfect way to begin your Route 66 journey.
15 Foods to Try in Chicago, Illinois
1. Chicago-Style Hot Dog
The Chicago-style hot dog isn’t just a meal—it’s an institution. This Windy City classic is comprised of an all-beef frankfurter nestled in a poppy seed bun and piled high with an iconic “salad” of toppings: yellow mustard, bright green relish, chopped onions, a juicy tomato wedge or two, a crisp dill pickle spear, a couple of sport peppers, and a dash of celery salt. But beware—ketchup is strictly off-limits! This flavor-packed creation is a perfect pit stop treat for anyone starting their Route 66 journey. To experience the best, check out some of these famous spots:
2. Deep Dish Pizza
Deep-dish pizza is a Chicago is a culinary experience everyone should try at least once. This thick, buttery crust is loaded with layers of gooey mozzarella, hearty toppings, and tangy tomato sauce piled on top (yes, the sauce goes last!). It’s a knife-and-fork kind of pizza, perfect for savoring every cheesy, melty, savory bite. It’s the perfect bucket-list-worthy bite for Route 66 road trippers fueling up for the epic journey ahead. To taste the real deal, head to one of these legendary spots:
3. Tavern Style Pizza
Deep dish might get all the press, but any Chicagoan will tell you that the true “Chicago-Style Pizza” is tavern style. Tavern-style pizza is thin, crispy, and cut into squares for sharing (or keeping all to yourself). This pub-friendly classic features a thin, crispy crust topped with a perfect balance of zesty tomato sauce, melty cheese, and toppings that reach every edge, ensuring no bite is left behind. Unlike its deep-dish cousin, this pizza is light enough to leave room for another round. Grab a slice at at one of these legendary spots:
Chicago Pizza Tour
Before taking off on your Route 66 adventure, explore one of Chicago’s most famous commodities: pizza. A Chicago Pizza Tour will take you around the neighborhoods to taste some of the best pies the city has to offer.
4. Chicago Mix Popcorn (Garrett Mix)
Chicago Mix popcorn (sold under Garrett Mix or other names due to copyright claims) is the city’s ultimate sweet-and-savory snack—a perfect pick-me-up before hitting Route 66. This addictive combo blends caramel popcorn’s rich, buttery sweetness with the bold, cheesy goodness of cheddar popcorn, creating a flavor explosion in every handful. It’s a little messy, a lot of fun, and totally worth the indulgence. Pick up an extra bag—you’ll thank yourself around mile marker 100! Stock up on this iconic treat at one of these shops:
5. Italian Beef Sandwich
The Italian beef sandwich is as Chicago as it gets. This hearty delight features thinly sliced, slow-roasted beef piled onto a crusty Italian roll, often topped with sweet peppers or spicy giardiniera for a flavorful kick. Order it dry (with gravy au jus on the side) if that’s your style but ordering it wet (with a little beef juice) or, my favorite, dipped (fully submerged in juice) is really the way to go. It can get MESSY so don’t forget to grab extra napkins if you’re taking this to go. Find this classic at legendary spots like:
6. The Palmer House Brownie
The Palmer House brownie is a Chicago-born dessert with a rich history. Created in 1893 at the iconic Palmer House Hotel for the World’s Columbian Exposition, the fudgy dessert is packed with walnuts and topped with a glossy apricot glaze, making it a decadent delight that stands out from the average brownie. Stop by the Palmer House Hilton to taste the world’s first brownie, which is still being made with the original recipe.
Chicago Favorites Ultimate Food and Walking Tour
Get a taste of the best foods of Chicago and a little taste of history too with a walking tour of downtown Chicago. Try deep dish pizza, a famous Chicago dog, and the brownie that started it all.
7. The Original Rainbow Cone
The Original Rainbow Cone is a Chicago institution that’s as colorful as it is delicious. This towering ice cream treat layers five incredible flavors—chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet—stacked in a signature wedge shape. Each bite is a journey of textures and tastes, from rich and creamy to bright and fruity. Perfect for cooling off on a summer day, you can savor this iconic dessert at the flagship Original Rainbow Cone in Beverly, at Navy Pier, or on the Magnificent Mile.
8. Maxwell Street Polish
The Maxwell Street Polish is a legendary Chicago street food bite with roots as rich as its flavor. This hearty sandwich features a juicy Polish sausage, chargrilled to perfection, nestled in a soft bun and topped with a generous helping of sweet grilled onions, tangy yellow mustard, and sport peppers for a spicy kick. Born on Maxwell Street, the sandwich became a staple of the city’s bustling open-air market and a must-try for visitors. Start your Route 66 journey with this flavorful bite at one of these iconic spots:
- Jim’s Original
- Original Maxwell Street
- Maxwell Street Depot
9. Ann Sathers Cinnamon Roll
Ann Sather’s cinnamon rolls bring comfort food to a whole new level. These giant, gooey rolls are swirled with cinnamon and sugar, then topped with a generous layer of rich, creamy icing that melts in your mouth. A staple at Ann Sather Restaurants, these sweet treats are the perfect way to start your day before hitting the road on Route 66—or to reward yourself after a day of exploring. Whether you grab one for breakfast or dessert, these cinnamon rolls are a must-try for any Windy City foodie.
10. Chicken Vesuvio
Chicken Vesuvio is a Chicago-born dish that’s as hearty as it is delicious. This Italian-American classic features bone-in chicken roasted to golden perfection alongside garlicky potato wedges, sweet green peas, and a flavorful white wine sauce infused with herbs like oregano and thyme. The result is a savory, tender meal that captures the warmth and comfort of Chicago’s culinary traditions. Try this local favorite at iconic spots like:
11. Fannie May Chocolates
Fannie May Chocolates have been a Chicago favorite since 1920, offering handcrafted confections that blend rich tradition with irresistible flavors. From the silky melt-in-your-mouth Pixies (a caramel and pecan delight) to the decadent chocolate-covered Mint Meltaways, every piece is a bite of pure joy. Perfect for gifting or snacking on the road, Fannie May’s iconic chocolates make a sweet addition to any Route 66 journey. Stop by a local shop to grab a box and savor a little taste of Chicago as you hit the highway!
12. Harold’s Chicken
Harold’s Chicken serves up crispy, flavorful chicken that’s been a local favorite since 1950. Taste perfectly fried chicken, golden and crunchy on the outside, juicy and tender on the inside, slathered in a signature mild or hot sauce. Get a side of white bread and fries to soak up every last drop. Before heading down Route 66, make a pit stop at one of their locations (there are a few in the Loop and West Loop) to taste a Chicago legend.
13. Pepper and Egg Sandwiches
The pepper and egg sandwich is simple, satisfying, and packed with flavor—a true blue-collar lunch staple. This hearty sandwich features scrambled eggs mixed with sautéed sweet bell peppers, all piled onto a crusty Italian roll. Popular as a meatless option for Lent, you can find it popping up as a Friday special around that time of year. But it has also become a year-round favorite at some local spots so you might be able to find it if you’re traveling in the summer too. Grab one of these sandwiches at a local favorite like D’Amato’s or Bari Subs.
14. Jibarito Sandwich
The Jibarito is a Chicago culinary treasure with Puerto Rican roots. Instead of bread, this unique sandwich uses crispy, flattened fried plantains to encase tender slices of steak, pork, chicken, or even veggies. It’s layered with garlic mayo, melted cheese, lettuce, and tomato for a flavorful, savory bite with a satisfying crunch. Created in Chicago’s Humboldt Park neighborhood, the Jibarito takes inspiration from other Latin American sandwiches, like the Venezuelan patacón and gives it a Puerto Rican twist. For an authentic taste, visit the place it was born at Borinquen.
15. A Classic Chicago Steakhouse
A classic Chicago steakhouse is more than just a restaurant—it’s a tradition steeped in rich flavors and timeless elegance. Known for perfectly aged, juicy cuts of beef, these iconic establishments offer everything from buttery filet mignon to robust ribeye, often served with sides like creamy mashed potatoes, sautéed spinach, or a crisp wedge salad. Whether you’re celebrating a special occasion or simply indulging, the ambiance of a Chicago steakhouse—dim lighting, leather booths, and impeccable service—takes the experience to the next level. Before hitting Route 66, treat yourself to a meal at legendary spots like:
Bonus: Jeppson’s Malört and the Chicago Handshake
Jeppson’s Malört is Chicago’s most infamous liquor, known for its bold, bitter flavor and a finish that lingers longer than a Lake Michigan winter. Made with wormwood, it’s an acquired taste to say the least—most first-timers brace themselves for the legendary “Malört face” that follows their initial sip (that is, if the person who sprung the shot on them even gave them a warning). “Enjoy” Malört at any local bar as a lone shot or as part of a “Chicago Handshake,” a city tradition that pairs a shot of Malört with a cold, refreshing Old Style beer.
Route 66 Restaurants in Chicago
Chicago marks the start of Route 66, and what better way to kick off your journey on the Mother Road than with some of the city’s most iconic eats? Let’s dive into the must-visit spots where Route 66 meets the Windy City’s legendary dining scene.
Lou Mitchell’s Restaurant
Start your Route 66 road trip off right with a good breakfast at Lou Mitchell’s restaurant in Chicago, Illinois.
Lou Mitchell’s opened in 1923 and its location at the start of Route 66 made it a quintessential stop before traveling the Mother Road. Choose from an impressive menu that hasn’t changed much from the start. Pancakes, waffles, and skillets are offered alongside the “world’s best” coffee, homemade bread, pastries, and fresh-squeezed orange juice.
Lou Mitchell’s is known as being “the first stop on the Mother Road” and was listed on the National Register of Historic Places in 2006.
The Berghoff Restaurant
Having opened in 1898, The Berghoff Restaurant in Chicago is older than The Mother Road itself. Herman Berghoff opened the restaurant after seeing the success of his beer stand at the 1893 World’s Fair and it has been (almost) continually operating ever since.
Located right on Route 66, The Berghoff became a popular destination for both locals and travelers alike. Stop in for some tasty German food and an ice-cold beer (or famous frosty root beer).
Chicago Food Festivals
When it comes to food, Chicago doesn’t just stop at iconic dishes—it throws some of the best food festivals in the country. These events are the perfect way to immerse yourself in the city’s diverse culinary scene, sampling everything from local classics to global flavors. If you’re a food lover hitting Route 66, make sure to time your trip to catch one of these tasty celebrations!
The king of them all is the Taste of Chicago, held every summer in Grant Park. This iconic festival, typically taking place in July, brings together dozens of local restaurants and food vendors, offering up bite-sized samples of their most popular dishes. From deep-dish pizza to tacos and vegan eats, there’s something for everyone. Plus, live music and family-friendly activities make it a full-on summer experience.
But the city doesn’t stop there. Other notable food festivals include the Ribfest Chicago in North Center, where BBQ lovers can indulge in some of the best ribs in the Midwest, and the Taste of Randolph Street, a West Loop celebration blending top-notch food from local restaurants with live music. Burger enthusiasts can’t miss the Roscoe Village Burger Fest, a summer favorite featuring creative takes on the classic American sandwich. For a taste of authentic Mexican cuisine, Mole de Mayo in Pilsen showcases the city’s best mole sauces alongside vibrant cultural performances. And for even more global flavors, the Chinatown Summer Fair offers a culinary journey through one of Chicago’s most historic neighborhoods.
No matter when you visit, Chicago’s food festivals are a surefire way to eat like a local and savor the flavors of the Windy City. So grab a plate, dig in, and let the city’s culinary spirit fuel your Route 66 journey! To find afestival that corresponds to your time in Chicago, check out the Choose Chicago guide.
As you gear up to hit the open road on Route 66, don’t forget to savor every bite of Chicago’s iconic food scene. From deep-dish pizza to the classic Chicago-style hot dog, these culinary treasures are the perfect way to fuel your adventure on the Mother Road. So, grab a bite, snap a pic, and let your taste buds kickstart an unforgettable journey through the heart of America.
Hungry for more of the best foods in Illinois and all of Route 66? Check out our guides to Iconic Illinois Eats, the Top Springfield Foods, and the 66 Must-Eat Dishes on Route 66.
Chicago Favorites Ultimate Food and Walking Tour
Get a taste of the best foods of Chicago and a little taste of history too with a walking tour of downtown Chicago. Try deep dish pizza, a famous Chicago dog, and the brownie that started it all.
