Welcome to Old Town
A pedestrian paradise with tree-lined streets and a lively nightlife
Although its name offers a nod to the neighborhood’s long-established roots, Old Town’s heart is decidedly young. With pretty, tree-lined streets and a hip after-hours scene, Old Town is so much more than simply a Chicago enclave that’s been around since the mid-1800s. This town was made for walking, and that’s just what its residents do. Whether taking in the stunning Victorian homes on a Sunday morning stroll or bar-hopping on a lively Saturday night, Old Town residents love being able to leave the car in the garage and explore this vibrant city on foot.
Founded in the 1850s by German settlers, Old Town gained the nickname of “The Cabbage Patch” because of the abundance of cabbage farmed by the new residents. The German settlers also built the neighborhood’s oldest Victorian building, St. Michael’s Church, one of the only buildings to survive the Great Chicago Fire of 1871. Now, this thriving arts and cultural hub is one you don’t want to miss.
What to Love
- Lively comedy scene
- Vibrant bistros and boutiques
- Leafy streets and high walkability
Local Lifestyle
With its European vibe and lively nightlife, Old Town offers its residents every opportunity to explore, have fun, and experience the good life. With art, entertainment, and a stellar culinary scene at their fingertips, locals tend to be cultured and curious. This educated and affluent community takes advantage of all Old Town has to offer, while leaving any kind of pretension or snobbery at the door.
Dining, Entertainment & Shopping
Travel back to the Old Town of the 1960s with a visit to The Old Town Ale House. This laid-back pub is known as the best dive bar in the city, and, considering it opened in 1958, it certainly has had time to secure its reputation. A neighborhood landmark, the Ale House features an old-school jukebox, funky art, and an eclectic clientele. Grab a drink or two here before heading to a show at nearby Second City, the world-famous comedy club where Amy Poehler, Bill Murray, and pretty much everyone on Saturday Night Live got their start. Catch a show, take a class, or stop in for the best burger and fries in town at 1959 Kitchen and Bar. This retro space, located at the Second City headquarters, offers elevated pub food, cocktails, and a jovial crowd.
In a town of long-established bars, Marge's clocks in as one of the oldest running taverns in Chicago. This wood-accented bar was opened in 1885 and serves craft beers, wine, and a creative menu that includes varied choices like seafood gazpacho, chicken pot pie, and mussels. For the best Italian food in Chicago, look no further than Topo Gigio. This cozy bistro offers an outdoor patio, an authentic menu of mouth-watering classics, and an extensive wine list.
Things to Do
In this dynamic community, even a trip to the flower shop turns into an artistic experience. Green Inc is an eccentric, family-run shop featuring potted plants, fresh-cut flowers, a variety of vases, statues, and bohemian objects. Old Town residents are in luck because this vibrant neighborhood is home to the Old Town Art Fair. Voted America's #1 Art Fair for four years running, this lively festival offers over 200 nationally acclaimed artists, a Garden Walk, live music, fun games, and activities for kids, food, drinks, and more. Snack on lobster rolls as you stroll the tree-lined streets of the charming Old Town Triangle District. You might even find that perfect painting for your new home.
For fun every night of the week, head out to explore Wells Street, Old Town’s buzzy hot spot for eats, drinks, and plenty of ways to be merry. This is where you’ll find Second City, The Old Town Ale House, and Topo Gigio, as well as pizza, burgers, and brews. For an experience that’s a bit more high-brow, head to the Chicago History Museum to learn how Chicago came to be the vibrant, thriving metropolis of today.
Schools
Old Town residents benefit from the area’s excellent public schools, including the highly-rated Lincoln Elementary, which teaches students in kindergarten through eighth grade.
