Old Town Chicago is one of my favorite neighborhoods in the city. It’s a vibrant, walkable part of the city, packed with history, charm, and, of course, some of the best food in Chicago. Whether you’re craving deep-dish pizza, an elevated steakhouse experience, or a casual brunch spot, Old Town has something for everyone. Over the years, I’ve tried my fair share of restaurants in Old Town, and these are my top 10 picks—places I keep coming back to because they never disappoint. Let’s dive in!
Where to Eat in Old Town
Old Town is a historic district and neighborhood in Chicago’s Near North Side and Lincoln Park. It’s a friendly and walkable neighborhood, and a popular spot for bars and restaurants ans with good reason. I spend a lot of time in the area, and here’s the thing I love about Old Town: you can always find a restaurant to fit your craving. Whether you’re looking to eat at a spot that’s casual and comfortable; or seeking more elegant dining experience, you’ll find it in Old Town.
EXPERT TIP: Looking for something to do after you grab a bite to eat? Check out our guide to comedy shows around the city, with many close by to the Old Town neighborhood, including the famous Second City and Zanies.
10 Favorite Places to Eat in Chicago’s Old Town
Broken English Taco Pub
📍 Location: 1400 N Wells St, Chicago, IL 60610
Whenever I’m in the mood for bold, authentic Mexican flavors, Broken English Taco Pub is my go-to. Inspired by Mexico City’s street food scene, this spot serves up some of the most flavorful tacos in town. The carne asada and crispy fish tacos are always winners, but I can never resist their elote-style street corn. Pair it with one of their potent margaritas—I love the spicy mango version for an extra kick. The graffiti-covered walls and lively vibe make it a fun and energetic place to grab a bite.
Benchmark
📍 Location: 1510 N Wells St, Chicago, IL 60610
When I’m looking for a fun night out, Benchmark is always a solid choice. This upscale sports bar blends contemporary American cuisine with a lively atmosphere, making it perfect for date nights or watching the game with friends. Their truffle fries are dangerously good, and I always find myself craving their juicy Benchmark Burger topped with smoked bacon and aged cheddar. For drinks, their handcrafted cocktails never disappoint—try the Blackberry Mule for something refreshing.
Happy Camper
📍 Location: 1209 N Wells St, Chicago, IL 60610
Happy Camper is my go-to when I’m in the mood for quirky, over-the-top comfort food. Their loaded appetizers are Instagram-worthy (think gooey cheese curds and loaded waffle fries), but the real star is their pizza. The crust is just the right mix of crispy and chewy, and I always go for The Dude—topped with sausage, caramelized onions, and hot honey. If you’re here for drinks, their boozy slushies are a must-try, especially on a warm Chicago afternoon.
Must-Try Dishes in Old Town: Burgers, Tacos, Pizza & More!
Small Cheval
📍 Location: 1345 N Wells St, Chicago, IL 60610
No visit to Old Town is complete without joining the line (trust me, it’s worth it) for one of Small Cheval’s celebrated smashed burgers. From the acclaimed Au Cheval team, this spot keeps things simple yet perfect—juicy patties, crisp lettuce, gooey cheese, and their signature sauce. Every bite is a nostalgic reminder of what a truly great burger should be. I always go for a classic cheeseburger with extra pickles and a side of golden, crispy fries. Don’t forget to wash it down with one of their rich, creamy milkshakes!
Corcoran’s Grill & Pub
📍 Location: 1615 N Wells St, Chicago, IL 60610
This Irish pub institution has been my go-to for hearty comfort food and a perfectly poured pint for years. There’s nothing quite like spending a summer afternoon at Corcoran’s on their spacious outdoor patio, enjoying a plate of fish and chips or a classic Reuben sandwich with a cold Guinness in hand. Inside, the warm wood tones and cozy atmosphere make it a great place to escape the Chicago chill. Whether you’re here for a laid-back meal, live music, or just a friendly pint, Corcoran’s always delivers on that welcoming Irish pub charm.
Burton Place
📍 Location: 1447 N Wells St, Chicago, IL 60610
Right on the corner of this lively neighborhood sits Burton Place—a three-story bar with an electric atmosphere perfect for any night out. It has been the setting for so many great get-togethers with friends. Their drinks are consistently solid, whether you’re sipping on a perfectly mixed Old Fashioned or grabbing an ice-cold beer. Their pub fare is underrated, and I especially love their late-night kitchen for post-bar bites. If you’re looking for a fun night out, this spot never disappoints.
EXPERT TIP: For those seeking a cold drink, check out our guide to Happy Hours, that will not disappoint around the city.
Old Town Pour House
📍 Location: 1419 N Wells St, Chicago, IL 60610
This lively, high-energy bar has been one of my go-to local haunts for years when I’m craving elevated pub grub like juicy burgers, crispy loaded nachos, and an extensive selection of craft beer. The spacious setting makes it an ideal gathering place, and with its central location, it’s the perfect pre-gaming destination before a night of bar-hopping in Old Town. If you love beer flights, Old Town Pour House is the place to explore unique and seasonal brews while enjoying a casual yet upbeat vibe.
Unwind and Savor: Rooftop Patios & Cozy Wine Bars
Utopian Tailgate
📍 Location: 1608 N Wells St, Chicago, IL 60610
As someone who loves a rooftop hangout, Utopian Tailgate is one of my favorite spots to spend a weekend. The vibrant, colorful rooftop is packed with bar games, making it a fun and energetic place to chill with friends all day. Their flavorful tacos, nachos, and craft margaritas are perfect for game-day gatherings. I always go for their house margarita with a side of their loaded nachos—it’s a winning combo every time.
The Vig
📍 Location: 1527 N Wells St, Chicago, IL 60610
If you’re looking for a cozy, upscale wine bar, The Vig is the place to be. Their globally inspired small plates pair beautifully with their impressive selection of wines, making it the ideal spot for a relaxed evening of grazing and sipping. Their truffle mac and cheese is a must-try, and I can never resist their expertly curated charcuterie board with a glass of bold red.
Orso’s Restaurant
📍 Location: 1401 N Wells St, Chicago, IL 60610
When I’m craving rustic yet refined Italian fare, Orso’s is my go-to Old Town gem. This charming neighborhood trattoria has been serving up pillowy gnocchi, wood-fired Neapolitan pizzas, and homemade pastas for years. The warm, inviting ambiance makes it perfect for a cozy date night or a leisurely dinner with friends. I always start with their bruschetta and finish with their tiramisu, which is as authentic as it gets.
No matter what you’re craving, Old Town has something delicious waiting for you. Whether you’re stopping in for a casual bite or a more refined dining experience, these spots offer fantastic food, drinks, and atmosphere. Cheers to good eats in one of Chicago’s most vibrant neighborhoods! 🍽️
BONUS: Best Restaurant in Old Town
Topo Gigio
📍 Location: 1516 N Wells St, Chicago, IL 60610
For classic Italian dishes in a lively, welcoming atmosphere, Topo Gigio is a must-visit. Known for its generous portions of pasta, fresh seafood, and traditional Italian entrees, this Old Town staple was a favorite of my husband’s Uncle John, who lived around the block from Old Town and ate here weekly. The veal saltimbocca is a personal favorite, and their rigatoni alla vodka never disappoints. The outdoor patio is a perfect spot for a warm summer evening, and their extensive wine list makes it easy to pair the perfect glass with your meal.
Savor the Flavor: Dive into in Chicago’s Old Town Restaurant Scene
No matter what you’re craving, Old Town has something delicious waiting for you. Whether you’re stopping in for a casual bite or a more refined dining experience, these spots offer fantastic food, drinks, and atmosphere. Cheers to good eats in one of Chicago’s most vibrant neighborhoods
As you wander the cobblestone streets, tantalizing aromas of sizzling cuisine and clinking glasses lure you to experience Old Town’s acclaimed dining scene firsthand. From long-standing establishment preserving beloved traditions to trailblazing hotspots dazzling with inventive fare, this enclave of Chicago offers an unrivaled array of flavors to discover.