Old Town is one of my favorite neighborhoods in the city — and Wells Street is one of the best restaurant strips in Chicago, full stop. It’s walkable, it’s friendly, and it has a rare quality: no matter what you’re craving, you can find it within a few blocks. Tuscan Italian from a spot that’s been open 35 years? Here. Smashed burgers from the Au Cheval team? Here. A rooftop with margaritas and bar games? Also here.
I spend a lot of time in Old Town, and these are the places I keep coming back to — the restaurants and bars that never disappoint, whether it’s a Tuesday night dinner or a Saturday afternoon that turns into a Saturday evening.
🍽️ In a Nutshell: Old Town’s restaurant scene is concentrated along Wells Street between North Avenue and Division Street — you can walk the whole strip in 10 minutes. The vibe is casual-to-upscale with a lean toward pub food, Italian, and creative American fare. Reservations are smart for Topo Gigio and The Vig on weekends; everywhere else is generally walk-in friendly. The neighborhood is especially fun on warm evenings when the patios and rooftops open up. Closest CTA stops: Sedgwick (Brown/Purple) and Clark/Division (Red Line).
⭐ Quick Picks
🇮🇹 Best Italian: Topo Gigio — 35+ year neighborhood icon, Tuscan-inspired, outdoor garden
🍔 Best Burger: Small Cheval — smashed burgers from the Au Cheval team
🌮 Best Tacos: Broken English Taco Pub — Mexico City street food vibes
🍷 Best Date Night: The Vig — wine bar with small plates and charcuterie
🍕 Best Pizza: Happy Camper — quirky, fun, boozy slushies
☘️ Best Patio: Corcoran’s — Irish pub with a spacious outdoor space
🏙️ Best Rooftop: Utopian Tailgate — bar games, margaritas, game day energy
Topo Gigio
📍 1516 N Wells St | topogigiochicago.com | Tue–Sat 11:30 a.m.–10 p.m. (10:30 Fri–Sat) | Sun 4–9 p.m. | Closed Mon | $$$
For classic Italian dishes in a lively, welcoming atmosphere, Topo Gigio is the essential Old Town restaurant. This Tuscan-inspired trattoria has been a neighborhood favorite for over 35 years — consistently voted one of the best Italian restaurants in Chicago — and it’s easy to see why. The portions are generous, the pastas are traditional and well-executed, and the outdoor garden is one of the best warm-weather dining spots on Wells Street.
This spot was a favorite of my husband’s Uncle John, who lived around the block and ate here weekly. The veal saltimbocca is a personal favorite, and the rigatoni alla vodka never disappoints. Their Sicilian-style pistachio tiramisu — made with cake instead of ladyfingers — is the way to end the meal. The extensive wine list includes bottles straight from Tuscany, and the covered outdoor bar is open year-round.
💡 INSIDER TIP: Make a reservation for weekend dinners — Topo Gigio gets packed. The outdoor patio is first come, first served. If you’re with a group of 35+, ask about the second-floor party room with vaulted ceilings and a full bar.
Small Cheval
📍 1345 N Wells St | smallcheval.com | Mon–Thu 11 a.m.–10 p.m. | Fri–Sat 11 a.m.–11 p.m. | Sun 11 a.m.–10 p.m. | $$
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 Au Cheval team — the restaurant that put Chicago’s burger scene on the national map — this spot keeps things simple yet perfect: juicy patties, crisp lettuce, gooey cheese, and their signature sauce. Every bite is a 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. The menu has expanded recently to include fried chicken, dipped cones, and craft cocktails. Indoor and outdoor seating available — you can also order ahead to skip the line on busy Friday nights.
Broken English Taco Pub
📍 1400 N Wells St | tacopub.com | $$
Whenever I’m in the mood for bold, authentic Mexican flavors, Broken English is my go-to. Inspired by Mexico City’s street food scene, this spot serves up some of the most flavorful tacos in town. The carne asada and crispy fish tacos are always winners, but I can never resist their elote-style street corn. Pair it with one of their potent margaritas — the spicy mango version has an extra kick that keeps me coming back. The graffiti-covered walls and lively vibe make it a fun and energetic place to grab a bite.
Orso’s Restaurant
📍 1401 N Wells St | orsosrestaurant.com | $$$
When I’m craving rustic yet refined Italian fare, Orso’s is my go-to Old Town gem. This charming, family-owned trattoria has been serving up pillowy gnocchi, wood-fired Neapolitan pizzas, and homemade pastas for years — right across the street from Topo Gigio, which gives you two excellent Italian options within steps of each other. 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. They also have a beautiful dining room and an Italian-inspired cocktail menu that’s worth exploring.
The Vig
📍 1527 N Wells St | thevigchicago.com | $$–$$$
If you’re looking for a cozy, upscale wine bar, The Vig is the place. Their globally inspired small plates pair beautifully with an impressive selection of wines, making it the ideal spot for a relaxed evening of grazing and sipping. The truffle mac and cheese is a must-try, and I can never resist their expertly curated charcuterie board with a glass of bold red. The Vig is one of the best date-night spots in Old Town — intimate without being stuffy.
Corcoran’s Grill & Pub
📍 1615 N Wells St | corcoransoldtown.com | $$
This Irish pub institution has been my go-to for hearty comfort food and a perfectly poured pint for years. There’s nothing quite like spending a summer afternoon on Corcoran’s spacious outdoor patio, enjoying a plate of fish and chips or a classic Reuben sandwich with a cold Guinness in hand. Inside, the warm wood tones and cozy atmosphere make it a great place to escape the Chicago chill. Whether you’re here for a laid-back meal, live music, or just a friendly pint, Corcoran’s always delivers on that welcoming Irish pub charm.
Happy Camper
📍 1209 N Wells St | happycamper.pizza | $$
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. The vibe is fun, colorful, and unapologetically casual.
Benchmark
📍 1510 N Wells St | benchmarkchicago.com | Tue–Fri 5 p.m.–close | Sat–Sun 11 a.m.–close | $$
When I’m looking for a fun night out, Benchmark is always a solid choice. This upscale sports bar blends contemporary American cuisine with a lively atmosphere, making it perfect for date nights or watching the game with friends. Their truffle fries are dangerously good, and I always find myself craving their juicy Benchmark Burger topped with smoked bacon and aged cheddar. For drinks, their handcrafted cocktails never disappoint — try the Blackberry Mule for something refreshing.
Utopian Tailgate
📍 1608 N Wells St | utopiantailgate.com | $$
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. This is Old Town’s best rooftop, hands down.
Old Town Pour House
📍 1419 N Wells St | oldtownpourhouse.com | $$
This lively, high-energy bar has been one of my go-to local haunts for years when I’m craving elevated pub grub — juicy burgers, crispy loaded nachos, and an extensive selection of craft beer. The spacious setting makes it an ideal gathering place, and with its central location, it’s the perfect pre-gaming destination before a night of bar-hopping in Old Town. If you love beer flights, this is the place to explore unique and seasonal brews while enjoying a casual yet upbeat vibe.
Burton Place
📍 1447 N Wells St | burtonplacechicago.com | $$
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.
Tips for Eating in Old Town
Getting there: Take the CTA Brown/Purple Line to Sedgwick or the Red Line to Clark/Division. Street parking is available but limited on weekend evenings — the neighborhood is compact and walkable, so transit or rideshare is often easier.
After dinner: Old Town is home to Second City and Zanies Comedy Club — two of Chicago’s most iconic comedy venues, both walking distance from Wells Street. Check out our guide to Chicago comedy shows for what’s on this week.
Happy hour deals: Several Old Town restaurants run happy hour specials, especially mid-week. Our guide to 25 happy hours in Chicago covers deals in and around the neighborhood.
Summer events: The annual Wells Street Art Festival (typically held in June) transforms the neighborhood into a street fair with live music, art vendors, and special menus from local restaurants. The OTMRA also hosts seasonal events like Bastille Day, Oktoberfest, and Progressive Dinner Wednesdays where participating restaurants offer $5 specials.
No matter what you’re craving, Old Town has something delicious within a few blocks. Cheers to good eats in one of Chicago’s most walkable and fun neighborhoods. 🍽️
A: Old Town is a historic neighborhood on Chicago’s Near North Side known for its tree-lined streets, comedy clubs (Second City and Zanies are both here), and one of the city’s best restaurant and bar strips along Wells Street. The neighborhood stretches roughly from Division Street south to North Avenue and is walking distance from Lincoln Park and the Gold Coast. Old Town is especially popular for its mix of casual pubs, Italian restaurants, rooftop bars, and late-night spots — all concentrated within a few walkable blocks.
A: Some of the best restaurants in Old Town include Topo Gigio (Tuscan Italian, a local favorite for 35+ years), Small Cheval (smashed burgers from the Au Cheval team), Orso’s (wood-fired Neapolitan pizza and homemade pasta), Broken English Taco Pub (Mexico City-inspired tacos and margaritas), and The Vig (upscale wine bar with small plates). For a casual night out, Corcoran’s Grill & Pub, Old Town Pour House, and Happy Camper are all popular choices along Wells Street.
A: Wells Street is the main commercial strip running through Old Town, roughly from North Avenue to Division Street. Most of Old Town’s restaurants, bars, and shops are concentrated along this stretch. The closest CTA stations are Sedgwick (Brown/Purple Line) and Clark/Division (Red Line). Street parking is available but limited, especially on weekend evenings — the neighborhood is very walkable from Lincoln Park, the Gold Coast, and River North.
A: Yes — Old Town is one of Chicago’s most walkable neighborhoods. Nearly all the restaurants and bars are concentrated along Wells Street within a 6–7 block stretch, making it easy to walk between spots. It’s also walking distance from Lincoln Park (north), the Gold Coast (east), and River North (south). The CTA Brown/Purple Line Sedgwick station and Red Line Clark/Division station are both nearby. Old Town is a popular bar-hopping neighborhood because everything is close together
A: Yes — many Old Town restaurants have outdoor seating, patios, or rooftop spaces. Topo Gigio has a popular outdoor garden and covered bar that’s open year-round. Utopian Tailgate has a colorful rooftop with bar games. Corcoran’s has a spacious outdoor patio. Small Cheval offers outdoor picnic tables. Summer is prime season for outdoor dining along Wells Street, and the Old Town Wells Street Art Festival (held annually in June) transforms the neighborhood into a street fair.