One Of Chicago's Hippest Neighborhoods Is An Artsy Gem With Victorian-Era Beauty And Cobbled Streets

One of the great things about Chicago is that you can feel like you traveled across several different cities without actually leaving Chicago itself — one neighborhood can feel like a completely other world from the next. The Mexican cuisine of Chicago's Little Village serves up rich flavors just miles from the colorful murals of the Wabash Arts Corridor, where street art transforms buildings into open-air galleries. Take a walk through the Old Town Triangle, and you'll step into a different kind of charm, one that blends beatnik energy with a historic atmosphere. This small but vibrant district is known for its picturesque cobblestone streets lined with trees and ornate 19th-century architecture.

Among the Old Town Triangle's postcard-worthy streets, the legendary Second City launched the careers of Mike Myers, Tina Fey, and countless other comedians who have shaped American humor. But there's more to this neighborhood than laughter. Old Town Triangle is also home to a lively bar scene, fantastic dining options, and the annual Old Town Art Fair. Located in central Chicago, just west of the Lincoln (Abraham) Park, the Old Town Triangle is easily accessible by the CTA Brown and Purple lines at Sedgwick station, or about an hour's drive from Chicago O'Hare International Airport. Once you arrive, walking is the best way to take in the beauty of this historic district.

The history of Old Town Triangle begins in the 1850s, when German immigrants settled in the area and built their community around St. Michael Church. Standing tall with its striking red brick facade and vaulted ceilings, the church is one of the most recognizable landmarks in the neighborhood. Many of the surrounding Victorian-style row houses were built after the Great Chicago Fire of 1871. Among them are some noteworthy landmarks, including the Henry Gerber House, a National Historic Landmark that once belonged to Henry Gerber, the founder of America's first gay rights society.

The neighborhood's name became concretized in the 1940s when the Old Town Triangle Association was formed. The group's efforts to foster a strong sense of community led to the creation of the Old Town Holiday, a fundraising event that evolved into today's Old Town Art Fair. Held every June, this fair features over 200 artists, a garden walk, live music, and incredible festival food.

Old Town Triangle's creative spirit continued growing in the 1950s with the opening of two institutions that are still integral to its identity today. The Old Town School of Folk Music became a center for musicians, offering lessons in everything from banjo to African drumming. Meanwhile, The Second City comedy club began making audiences laugh in 1959, eventually launching some of the biggest names in entertainment (the full list of names would take up this whole article). Catching a show here is a must — you never know if you're watching the next comedy superstar.

Old Town Triangle has plenty of dining options that have made their mark in history with mouthwatering flavors. Twin Anchors, a restaurant dating back to the 1930s, serves up legendary baby-back ribs that were a favorite of Frank Sinatra. If Italian comfort food is more your style, Orso's Italian Restaurant will "transport you to an Italian family meal experience," as Tripadvisor reviewer @TrailBlazer426514 described, with its vintage ambiance and garden seating. And for a no-frills, all-flavor experience, Small Cheval — the more modest version of West Loop's Au Cheval — specializes in nostalgic American fare (think burgers, fries, and milkshakes) which you can savor on its outdoor picnic benches.

When it comes to nightlife, Wells Street is where the action happens. While it may not have the same scandalous reputation it once did — Time referred to it as part of "The Porno Plague" in the '70s — it's still one of the city's most boisterous strips. One bar you definitely can't miss is the Old Town Ale House, a beloved watering hole that's been serving drinks since 1958. Anthony Bourdain loved the bar, and it's easy to see why. With a jukebox, eccentric artwork by the owner hung on the walls, and a crowd of locals who have stories to tell, it's the perfect place to end your night. Just remember: While fun is center-stage, handling your booze correctly is one of the unwritten rules of Chicago to know before your visit.