How I'd Explore Chicago's Old Town, Coming From A Local

If you want to experience Chicago beyond the usual tourist traps, I'd start in Old Town. I moved to the neighborhood sight unseen when I first came to Chicago and fell in love with its tree-lined streets, locally owned shops, and global cuisine options. And with a Walk Score of 97, visitors can ditch the car and spend a full day here on foot.

My perfect day in Old Town starts slowly. I'd stroll the Division Street Farmers Market while it's in season before wandering toward North Wells for brunch. From there, you can spend the afternoon popping into independent boutiques, browsing a basement bookstore, admiring one of Chicago's oldest churches, or settling in for a cup of coffee or an inventive cocktail. As the afternoon winds into evening and street lights illuminate Old Town, the restaurant and bar scene comes alive. Whether you're craving unique French cuisine, Peruvian fusion, classic Italian, or a neighborhood pub, there's no shortage of places to settle in for dinner. And if you still have energy afterward, you're only a few steps from some of Chicago's most iconic comedy and nightlife venues.

Old Town is a perfect blend of history and vibrant energy with Victorian-era beauty and cobbled streets. It's also one of those Chicago neighborhoods where I think it pays to wander without a strict itinerary. Let yourself get distracted by a shop, restaurant, bar, or tucked-away corner along the way. Here's exactly how I'd spend a day exploring Old Town as a local.

The Division Street Farmers Market is open from 7 a.m. to noon every Saturday, from May through October, and offers a range of products. It is my favorite way to spend a Saturday morning — I especially love selecting fresh, seasonal produce from local farmers and chatting with the vendors. Depending on the season, you'll find regional fruits and vegetables, baked goods, specialty foods, and other locally made products. I recommend arriving earlier in the morning to take your time exploring before the crowds pick up.

If you're looking for a lively introduction to your day, grab a table at Happy Camper for boozy brunch and morning events ranging from bingo to bottomless mimosas. I especially love their pizzas — the Nadene and Lance are standouts. For a classic diner vibe, head north to Nookies. This longstanding institution has been open for over 50 years and serves gigantic portions and ever-flowing coffee. If you're in a hurry, another favorite of mine is Wells Street Kitchen and Juice for a quick bite or beverage.

Chicago is filled with architectural wonders, but one of the oldest buildings is right in my neighborhood. The St. Michael Catholic Church was built in the late 1860s, and its walls even survived the Great Chicago Fire, which leveled much of the neighborhood. Its towering presence makes it hard to miss as you walk through Old Town, and stepping inside offers an even greater appreciation for its history and craftsmanship. The church was built to serve the neighborhood's growing German Catholic population and has remained an important part of the community for generations.

Plenty of local boutiques fill the avenue on North Wells. Stop in Judy Maxwell Home, where "Shameless" star Joan Cusack is the founder and makes an occasional appearance. Slant of Light Books is a basement bookshop with community events, and you can even buy local spices and oils from Old Town Oil and The Spice House. Head north to Green Inc to be surrounded by an array of foliage and flowers for sale. I also like to pick up my annual herb and tomato plants from Old Town Gardens each spring, but they also provide seasonal pumpkins and evergreen trees.

One of the most anticipated new openings in Old Town is Rest + Recreation, which will feature inventive coffee and cocktails. Whenever I need to grind on work, I like to head to Kapej Coffee Roasters on North Sedgwick; beyond coffee, they make an excellent bagel sandwich. If a cocktail is more your vibe, Utopian Tailgate offers some of the best views in the neighborhood in a lively setting. Alternatively, you could walk in the footsteps of Anthony Bourdain and grab a pint at the historic Old Town Ale House or head down below North Wells to the intimate speakeasy Caché.

One of the best higher-end dinner options in Old Town is Gavroche, an inventive French joint with limited seating, or the Peruvian fusion restaurant Kayao. Orso's and Topo Gigio compete for best Italian joint in the neighborhood, but my vote goes to Orso's for its live pianist on weekends and jalapeño gnocchi with vodka sauce. Beyond that, I also frequently visit Nepal House, Kamehachi for sushi, and Twin Anchors for barbecue. I'd recommend making a reservation for some of the smaller or more popular restaurants, particularly if you're visiting on a weekend.

Chicago has long been a center of American comedy culture, and I'm lucky to have two iconic clubs just a few blocks from my apartment. The Second City is the largest and most recognizable — it has launched the careers of comedy powerhouses like Tina Fey, Amy Poehler, Steve Carell, and John Belushi, as well as recent faces on "Saturday Night Live" like Aidy Bryant, Cecily Strong, and Tim Robinson. You're almost guaranteed to see a future SNL cast member when you visit. Right down the block, Zanie's is a more intimate venue with table seating and newer faces in the comedy world.

Old Town tends to get particularly energetic on weekend nights, when North Wells fills with people moving between bars and restaurants. Some that I like to visit are Burton's Place for casual vibes, Declan's Irish Pub for a pint of Guinness and outdoor sports viewing, or Winnie's Chicago when I'm looking for a cocktail with friends. Fireplace Inn, Benchmark, and the upper-floor lounge Blue Leopard are other more lively options for dancing and mingling. I also love heading a few blocks into Gold Coast to visit the Hange-Uppe, the iconic Irish pub Butch McGuire's, and the speakeasy-esque rum bar Sparrow.

Lodging in Old Town is limited, so I typically direct people to stay at the Level Chicago Old Town, which, name aside, is right over the border in Gold Coast. They offer apartment-style living directly on North Wells with amenities including a first-floor coffee shop and wine bar, seasonal pool, fitness center, sauna, spa, and secured parking. I also like the Hotel Lincoln, which is a Hyatt property on the north end of Old Town. The hotel features views of Lincoln Park and is within walking distance of the Lincoln Park Zoo, one of America's oldest.