Old Town is one of the most iconic neighborhoods in Chicago, known for its historic charm, cobblestone streets, and most importantly, an incredible dining scene. Whether you are a Chicago local or a visitor looking for the best Old Town Chicago restaurants, this neighborhood offers a cozy, residential feel by day and a legendary nightlife scene by evening.
From hidden gem cafes to world-class comedy, here is how to spend a perfect day eating and exploring your way through Old Town.
Start your morning at La Fournette, an authentic Alsatian bakery that is a staple among Old Town Chicago restaurants. Their Croque-Monsieur is a legendary, out-of-this-world ham and cheese sandwich dripping in rich béchamel sauce. Pair it with one of their signature macarons (the pistachio is a must-try) for a breakfast that feels like a quick trip to Paris.
After breakfast, take a stroll down Wells Street. Two shops you cannot miss are The Spice House and Old Town Oil.
The Spice House: Known for the finest spices in the city, their "Old Town" blends and imported Saigon Cinnamon are favorites for home cooks.
Old Town Oil: They offer a wide assortment of high-quality olive oils and balsamic vinegars. We recommend the Tuscan Herb EVOO and the Lemon White Balsamic.
Both shops offer unique Chicago gifts and are a testament to the artisan spirit that makes shopping and dining in Old Town Chicago so special.
For a true taste of the neighborhood, there is no better spot for lunch than Old Jerusalem. A fixture on the list of must-visit Old Town Chicago restaurants since 1976, their falafel sandwich is a masterclass in Mediterranean flavors: deep-fried chickpea patties, fresh vegetables, and specialty house-made sauce. If you’re craving meat, the Chicken Shawarma is a local favorite. Don’t leave without a piece of their honey-drenched Baklava!
The Fudge Pot is an Old Town classic that has been hand-crafting treats since 1963. Their most addictive creation is the butter toffee, but you can’t go wrong with their chocolate-covered strawberries or custom-molded chocolates. It’s the perfect mid-afternoon pick-me-up as you explore the historic side streets.
View this post on Instagram
Chicago is a city built on stories. While you're in the area, the Chicago History Museum is just a 5-minute walk from the heart of Old Town. It’s a great spot for both kids and adults to learn about the Great Chicago Fire, the city’s jazz age, and evolving cultural exhibits.
View this post on Instagram
After a day of exploring, head to Happy Camper for the ultimate dinner with the ultimate vibes. This is one of the most popular Old Town Chicago restaurants for groups, featuring a massive patio, tire swings, and neon lights. Their pizza menu is extensive, featuring creative toppings and excellent dairy-free options.
View this post on Instagram
No culinary tour is complete without dessert. Jeni’s Splendid Ice Creams on Wells Street is the perfect final stop. Their ice cream is made with grass-pastured milk and whole ingredients. Try unique fan-favorite flavors like Goat Cheese with Red Cherries or Brambleberry Crisp.
Conclude your night at the world-famous Second City. As the training ground for legends like Tina Fey, Steve Carell, and Bill Murray, it remains the premier spot for improv and sketch comedy in the world. Catching a show here is the quintessential Old Town experience.
If you don't have a whole day to explore on your own, let the experts at Chicago Food & City Tours show you the way! We specialize in connecting hungry locals and visitors with the best stories and flavors in the city.
Looking to dive deeper into the Chicago food scene? Check out our most popular experiences:
Iconic Foods of Chicago Tour: The ultimate "must-eat" tour featuring deep dish pizza, Chicago-style hot dogs, and Italian beef.
Gateway to the West Loop Tour: Explore the "Restaurant Row" of Chicago and taste why this neighborhood is a global culinary destination.
The Chinatown Adventure: A cultural immersion through one of Chicago's most vibrant neighborhoods.
Whether you're looking for a public walk or a private tour, Chicago Food & City Tours has you covered. Our expert Food Ambassadors will lead you on a delicious journey through Chicago's history and its most legendary eateries. Book your tour today!
You Might Also Like
16 Chicago Bachelorette Party Ideas to Inspire Your Weekend Itinerary
The Best Wicker Park Restaurants: Why Division Street is the New Foodie Mecca
