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Old Town
Profile
Old Town is effortlessly classy, a little bit artsy, full of energy — and somehow consistently cool. It has plenty of calm and peaceful streets, scattered with fun commercial pockets. There are rows of cute cafes and historic pubs, along with used book stores and small independent shops. The neighborhood also has a thriving bar and restaurant scene, while maintaining a warm, charming feeling over the years.
You’ll find beautiful condos, high-end single family homes, and well-preserved buildings with decorative brickwork and archways. When you’re ready for a night out, most of the action is in the northern part of the neighborhood, known as the Old Town Triangle. And when you want to get out and explore, Old Town is just two miles north of downtown Chicago, and a mile from the lake.
Old Town is an afternoon stroll down historic streets, dotted with wrought iron accents and patches of greenery. It’s the belly-aching laughter of finding your favorite new comedian. It’s Sunday brunch in a cozy booth, followed by an afternoon art festival just down the road. It’s a gleaming sunset as you make your way home at the end of a perfect weekend.
Backstory
Way back in the early days, Old Town’s settlers planted a lot of vegetables, including massive amounts of cabbage. This earned the area its first nickname, “The Cabbage Patch.”
But then, in the Great Chicago Fire of 1871, nearly every home and building in the neighborhood burned down. One of the only survivors was St. Michael’s Church, which still stands today.
While the rest of Chicago was rebuilt on a grid layout, Old Town retained some of its ramshackle charm. The area known as Old Town Triangle is full of winding streets, narrow one-way alleys, and asymmetrical intersections.
A neighborhood committee called The Old Town Triangle Association was formed in the 1940s to preserve the character and history of the area — and they’ve been doing so ever since. Each June the association hosts the Old Town Art Fair, one of the best art shows in the country, with live music and food stalls galore.
Local Fare
- Cocoa + Co: Part chocolatier, part bakery, part cafe, with an amazing selection of pastries and single-origin chocolate bars. Make sure to try their dark hot chocolate.
- Kamehachi: Chicago’s oldest sushi bar has been around for decades. It’s a great spot for dinner, and they also offer bento box lunch specials during the week.
- Topo Gigio Ristorante: Their homemade pasta is simply phenomenal. The atmosphere is laid back, casual, and fun — and they have a patio for the warmer months.
- Small Cheval: Enjoy the life-changing burgers of Au Cheval, but in a more casual setting, and without the multi-hour wait times. The Old Town edition has a full bar and a cute outdoor area, too.
- Happy Camper: Hot pizza and cold beer with a laid-back party vibe. The bar is built into a chrome trailer, and the dining room is decorated with neon signs and twinkle lights.
- Broken English: Enjoy tacos and margaritas in a fun, funky space that’s painted from floor to ceiling in brightly colored murals.
- The VIG: An upscale sports lounge with 1950s styling and a chic/sophisticated feel. You can watch the game while nibbling on elevated bar food and sipping IG-ready cocktails.
- Twin Anchors: This long-standing dive bar is known for frosty beers and tangy baby back ribs. It was frequented by Frank Sinatra, and is one of the oldest restaurants in the city.
Things to Do
- Second City: Chicago’s beloved home of improv comedy, this place has introduced the world to more famous comedians and actors than you can count — Steve Carell, Tina Fey, Eugene Levy, Amy Poehler, Bill Murray, and Stephen Colbert are just a few examples. Locals have been catching shows here since it opened in 1959.
- Zanies: A legendary stand-up comedy club open 7 nights a week, this place is an institution and a piece of living history. The late-night shows are a lot of fun, especially after you hit your two drink minimum.
- Old Town Ale House: Serving drinks since 1958, the walls are covered in portraits of famous regulars like Bill Burray, as well as some evocative satirical paintings — many painted by the owner. Anthony Bourdain once called this the best dive bar in Chicago.
Sights to See
- Henry Gerber House: Chicago’s Old Town was home to America’s first gay rights organization — 1704 North Crilly Court, now known as Henry Gerber House. Today, the house is a national landmark.
- Chicago History Museum: Located on the south end of Lincoln Park proper/north end of Old Town, this place has been around since the mid-1800s. Exhibits range from Abraham Lincoln and the Civil War to music and newspaper photography, plus there are various walking tours and special events. They also have the very first L car on display.
- St Michael’s Church: This gorgeous Roman Catholic church was completed in 1869, and at the time its tower made it the tallest building in the country (though that didn’t last long). With its incredible brickwork, it’s one of the only buildings that survived the Chicago Fire.
Transportation
The Brown and Purple CTA lines run through the Sedgwick stop, and you can catch the Red line just southeast of Old Town at Clark/Division. There are bus stops on nearly every corner, making it super convenient to zoom around the neighborhood, and overall it’s a very walkable area.
- the Loop: ~25 min by public transit
- the Lake (North Ave. Beach): ~20 min walk
- Lincoln Park Zoo: ~10 min walk
- Rush St. Dining (Gold Coast): ~15 min by public transit; ~30 min walk
- O’Hare: ~60 min by public transit
- Midway: ~60 min by public transit
