Chicago is a food lover’s paradise. From world-famous deep-dish pizza to beloved local specialties like the Italian beef sandwich, the city offers an impressive array of culinary experiences that will leave your taste buds begging for more. Whether you’re planning a quick weekend getaway or a 72-hour trip, this ultimate Chicago foodie guide will lead you to the must-try dishes and the best spots to savor them. Get ready to explore Chicago’s dynamic food scene, one delicious bite at a time.
1. Deep-Dish Pizza: The Classic Chicago Staple
No trip to Chicago is complete without indulging in the city’s legendary deep-dish pizza. This thick, buttery crust, loaded with cheese and chunky tomato sauce, is an absolute must-try for any visitor. While several pizzerias claim to have the best pie in town, a few spots stand out from the rest.
Where to Try It:
- Lou Malnati’s: One of the pioneers of deep-dish pizza, known for its buttery, flaky crust and rich, cheesy center.
- Giordano’s: Famous for its stuffed deep-dish pizza, offering layers of cheese and a generous helping of tomato sauce.
- Pequod’s: Known for its caramelized crust and slightly crispier edge, it’s a local favorite for those in the know.
Pro Tip: Don’t expect a quick meal—deep-dish pizza can take up to 45 minutes to bake, so sit back, relax, and enjoy the experience!
2. Chicago-Style Hot Dog: A Flavor Explosion
The Chicago-style hot dog is a culinary institution. Served on a poppy seed bun and topped with mustard, relish, onions, tomatoes, sport peppers, a pickle spear, and a sprinkle of celery salt (but never ketchup), it’s a flavor explosion that you have to try at least once.
Where to Try It:
- Portillo’s: A fast-casual icon, Portillo’s serves one of the most authentic Chicago-style dogs in the city.
- Superdawg Drive-In: An old-school drive-in known for its snappy hot dogs and retro atmosphere.
- Gene & Jude’s: Consistently ranked as one of the best, this spot offers a classic dog with fries piled on top.
Pro Tip: If you ask for ketchup, be prepared for some side-eye. It’s a big no-no in Chicago!
3. Italian Beef Sandwich: A Local Favorite
The Italian beef sandwich is another beloved Chicago dish. Thinly sliced roast beef, soaked in au jus, piled on a long Italian roll, and topped with either sweet peppers or spicy giardiniera—this sandwich is a messy, flavorful masterpiece.
Where to Try It:
- Al’s Beef: The original and arguably the best, Al’s Beef has been serving up Italian beef sandwiches since 1938.
- Mr. Beef: A local favorite offering tender beef and perfectly seasoned gravy.
- Johnnie’s Beef: Known for its no-frills atmosphere and legendary beef sandwiches, it’s a must-visit spot for beef lovers.
Pro Tip: Order your sandwich “dipped” for an extra-soaked, extra-delicious experience!
4. Garrett Popcorn: Chicago’s Sweet and Savory Treat
For a snack that’s both sweet and savory, Garrett Popcorn is a must-try. The signature Garrett Mix, a combination of caramel and cheese popcorn, has become a local staple that you can find throughout the city.
Where to Try It:
- Garrett Popcorn Shops: With locations all over Chicago, it’s easy to grab a bag of this delicious treat wherever you are.
- Chicago O’Hare International Airport: Perfect for picking up a souvenir snack before your flight home.
Pro Tip: Be prepared to stand in line during peak hours—it’s that popular!
5. Jibarito: A Puerto Rican Delight
The Jibarito sandwich is a Puerto Rican creation unique to Chicago. Instead of bread, crispy fried plantains serve as the base for this sandwich, which is typically filled with steak, garlic mayo, lettuce, and tomatoes. It’s a must-try for anyone looking to explore the city’s diverse culinary landscape.
Where to Try It:
- Borinquen Lounge: Known as the birthplace of the Jibarito, this restaurant is the go-to spot for an authentic taste.
- Papa’s Cache Sabroso: A neighborhood favorite offering mouthwatering variations of the Jibarito.
- El Nuevo Borinquen: Another excellent option for this delicious sandwich, served with a side of Puerto Rican rice and beans.
Pro Tip: Try pairing your Jibarito with a cold tropical drink for the full experience!
6. Maxwell Street Polish: Chicago’s Best-Kept Secret
This flavorful sausage served on a bun with mustard, grilled onions, and sport peppers, is a Chicago street food classic. While not as widely known as the deep-dish pizza or hot dog, the Maxwell Street Polish is a hidden gem for those in the know.
Where to Try It:
- Jim’s Original: Located near the original Maxwell Street Market, this is the go-to spot for the authentic experience.
- Express Grill: Another iconic spot serving the Maxwell Street Polish with all the fixings.
- Portillo’s: Though famous for hot dogs, Portillo’s also offers a solid version of this local favorite.
Pro Tip: This hearty dish is perfect for a quick bite between sightseeing stops!
7. Chicago-Style Popcorn: The Ultimate Snack
Chicago’s love for popcorn goes beyond Garrett Mix. Whether you're craving sweet, salty, or savory, the city’s gourmet popcorn shops have you covered.
Where to Try It:
- Garrett Popcorn Shops: The signature mix of cheese and caramel popcorn is the city's favorite snack.
- Nuts on Clark: Offering a wide range of popcorn flavors, from traditional butter to exotic blends.
- Chicago Kernel: Another local favorite known for fresh, flavorful gourmet popcorn.
Pro Tip: Buy an extra bag to bring home—it’s a perfect souvenir of your Chicago trip!
8. Chicago-Style Tamales: A Unique Twist on a Classic
Unlike traditional Mexican tamales, Chicago-style tamales are wrapped in paper and feature a finer, grittier texture. Often sold at hot dog stands, they’re an unexpected yet beloved part of the city’s culinary fabric.
Where to Try It:
- Tom Tom Tamales: The company that’s been serving these unique tamales for over 80 years.
- Fat Johnnie’s Famous Red Hots: Not only great for hot dogs but also a top spot for Chicago-style tamales.
Pro Tip: Pair them with a Chicago-style hot dog for a truly unique meal!
9. Steakhouse Experience: The Best of Chicago’s Fine Dining
Chicago is home to some of the country’s best steakhouses, where you can indulge in a perfectly cooked ribeye or filet mignon. These restaurants offer an unforgettable dining experience, perfect for foodies seeking upscale meals.
Where to Try It:
- Gibsons Bar & Steakhouse: A Chicago institution known for its prime steaks and legendary martinis.
- Chicago Cut Steakhouse: Offering beautiful views of the Chicago River along with its impeccable cuts of beef.
- RPM Steak: A modern steakhouse that offers a mix of classic and innovative dishes, ideal for foodies looking for something different.
Pro Tip: Make a reservation well in advance, especially on weekends!
10. Chicago-Style Cheesecake: A Sweet Finish
After indulging in Chicago’s savory delights, a slice of rich, creamy cheesecake is the perfect way to end your foodie adventure. Chicago’s bakeries offer some of the best cheesecakes you’ll find anywhere.
Where to Try It:
- Eli’s Cheesecake: The most famous cheesecake in Chicago, with flavors ranging from classic to indulgent variations.
- Mindy’s Bakery: Known for its creative takes on traditional desserts, including a fantastic cheesecake.
- Vanille Patisserie: Offers an array of decadent desserts, including creamy, flavorful cheesecakes.
Pro Tip: Bring a slice back to your hotel or Airbnb for a late-night treat!
Chicago’s food scene is as diverse as the city itself. Whether you’re digging into a deep-dish pizza or savoring a Jibarito, the Windy City offers something for every palate. Use this ultimate foodie guide to explore the best must-try dishes and discover why Chicago is a dream destination for food lovers. With so many options to taste and explore, your 72-hour trip will be filled with unforgettable culinary experiences.For more travel tips and inspiration, follow us on Instagram, YouTube, and TikTok, and join our Facebook group to connect with other travelers! Don’t forget to tag your travel photos #72HourAdventures for a chance to have your trip featured on platforms.
