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Chicago has a stunning modern skyline of skyscrapers that peer Lake Michigan. However, one of the most charming aspects of the city may be its Old Town, a modern representation of Chicago, complete with winding nonsensical streets.

Travelers to Chicago should take some time to check out Chicago’s Old Town. It has too much to offer visitors while also being quite convenient to reach. Here is what to expect from Chicago’s Old Town.

Old Town Chicago, And Everything Official And Unofficial About It

Neighborhoods quite frequently have hard-to-define borders. Old Town Chicago isn’t much different. However, it’s hard for a traveler not to notice the change in the air, the shift to tree-lined sidewalks, and the strong sense of community that emanates from Old Town Chicago.


Sitting two miles north of downtown Chicago and a mile west of the lake, Old Town is an incredibly accessible area surrounded by some great neighbors. These neighbors include the Gold Coast to the east and Lincoln Park to the north.

Old Town Border

There may not be official borders, but the unofficial official, according to the City of Chicago data portal, says that Old Town encompasses 64 acres and is split by North Avenue, which runs straight through its middle.

Overall, the area of Old Town isn’t too large. It measures one mile north to south and a little less than that east-to-west. The total perimeter measures out to be just over 3.1 miles long.

Old Town Triangle

If Old Town could be said to have a centerpiece, it would be the Old Town Triangle. It has been widely known since the 1950s as being one of, if not the best, areas in this neighborhood to check out.

Related: 10 Things To Do At Chicago's Riverwalk

A Brief History Of Old Town

Old Town Chicago started as a little German settlement that has turned into an iconic and classic neighborhood in modern-day Chicago.

The Cabbage Patch

The Cabbage Patch was actually Old Town’s original name. The area was developed by German settlers even before it was within Chicago’s city limits. These German settlers are responsible for my of the treasures in the modern city, such as St. Michael's Church. It was first built in 1869 and was fortunate enough to survive the Great Chicago Fire.

A New Old Town

Though the rest of the city was rebuilt using a grid system after the fire, Old Town elected to maintain its classic road system as it was, full of narrow one-ways and asymmetrical intersections. It helps Old Town stand out a bit with its classic charm.

With fire-resistant bricks, stone and stucco, the German settlers rebuilt Old Town. They made many eclectic choices and prided themselves in the aesthetically pleasing and masterfully-crafted row houses and apartment buildings. Travelers to Old Town can partake in an Old Town Architecture Tour to learn more about the neighborhood.

Surviving The Depression And North Well Revolution

As it did in many places, the Depression wasn’t easy on the neighborhood of Old Town. But in the 1940s, the neighborhood from the Old Town Triangle Association. They have been an incredibly active community organization that has worked to push, promote, and improve Old Town.

In the 1960s, Old Town began to develop a bit more past what it had previously been. N. Wells Street, which runs through the eastern side of the neighborhood, became a bit of a must-be location. It was both important and fashionable to be seen on the street there.

Related: Is The Chicago Skydeck Worth It? Here's What You'll See

Today’s Old Town And What To Expect

Today’s Old Town echoes many of the same qualities that were unique to its former self. Residents have stayed put, and Old Town Triangle Association has become more and more active. This has helped the neighborhood embrace modernism and change while retaining much of its former self.

Travelers to Old Town today can expect to find a transition between classic charms on every street corner. Architecture from different eras mingles together on the same street corners. Creating an incredible atmosphere that travelers should definitely check out.

The Rabbit Hole

Located literally on the threshold of Old Town’s entertainment district, The Rabbit Hole is a popular go-to destination that attracts visitors for a multitude of reasons. The Rabbit Hole offers great pub food, light fare, and hearty fare while also offering up a magical nightlife experience.

  • Address - 1208 N Wells St N Wells St. & W Division St., Chicago, IL 60610-1906
  • Contact - 312-274-1824
  • Cost - $$-$$$
  • Must-Try - Burgers and Cocktails
  • Menu

Fox Trot Market

The Fox Trot Market is a grocery store and café on Wells near North Avenue. Travelers venturing in here can expect the welcoming aroma of coffee as well as anything else that they may be looking for.

Topo Gigio

At the center of Old Town, Travelers can discover Topo Gigio. This restaurant offers a modern Tuscan-style of Italian Cooking. Topo Gigio annually ranks amongst the best Italian restaurants in the city and is a staple of Old Town.

  • Address - 1516 N Wells St, Chicago, IL 60610-1308
  • Contact - +1 312-266-9355
  • Cost - $$-$$$
  • Must-Try - Lake Superior whitefish
  • Menu

Jeni’s Splendid Ice Cream & La Fournette

This will easily rank amongst the best ice cream experiences a traveler will have. With so many delicious and creative flavors, it is impossible to leave Jeni’s shop unsatisfied.

  • Address - 1954 Hillhurst Ave, Los Angeles, CA 90027
  • Contact - (323) 928-2668
  • Hours - 11 am to 11 pm
  • Health & Safety - Safety dividers at checkout
  • Menu