Old Town, Chicagoland Travel Guide

Experience the vibrant history and unique charm of Old Town, Chicago, a captivating neighborhood filled with culture, art, and culinary delights.

Old Town, a historic neighborhood in Chicago, offers a delightful blend of charming architecture, vibrant culture, and an array of dining and shopping experiences, making it a must-visit for tourists seeking an authentic Chicago experience.

A brief summary to Old Town

Chicago, Old Town, Illinois, US

From Eve

Know before you go

Hi, I'm Eve. Here are a few practical things to know before exploring Old Town.

Take a guided walking tour to learn about the rich history and architecture of Old Town.
Visit the Old Town Art Fair, held annually in June, for a taste of local art and community spirit.
Make dinner reservations at popular restaurants to avoid long wait times, especially on weekends.
Explore the local shops for unique souvenirs and handmade gifts that capture the essence of Chicago.

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Explore Old Town on the Map

A handpicked selection of must-see spots near Old Town, mapped for you.

Getting There

Public Transit - Train

From any location in Naperville, make your way to the Naperville Metra Train Station located at 105 E 4th Ave. Board the BNSF Railway Line train heading towards Chicago Union Station. The train ride takes approximately 35 minutes. Once you arrive at Chicago Union Station, exit the train station and head towards the Canal Street exit.
Public Transit - Bus

If you prefer to take the bus, locate the nearest bus stop for the Pace Bus service. Take the Pace Route 714 towards the Downers Grove Park-n-Ride. From there, transfer to the Pace Route 855 towards Chicago. Get off at the stop at North Avenue & Wells Street. Walk north on Wells Street for about 10 minutes until you reach Old Town.
Walking

If you are already in downtown Naperville, you can also take a leisurely walk to the train station if it’s within a reasonable distance. Simply head towards the riverwalk and follow the path to the train station, which is about a 20-minute walk. Once you reach Chicago Union Station, follow the Canal Street exit to get to Old Town.

Discover more about Old Town

Old Town is one of Chicago's most enchanting neighborhoods, characterized by its well-preserved Victorian architecture and cobblestone streets. This area is a delightful blend of history and modernity, where visitors can stroll through the picturesque streets lined with boutique shops, art galleries, and cozy cafes. The neighborhood is renowned for its rich cultural heritage, serving as a hub for artistic expression and community events. One of the highlights of Old Town is the iconic Second City, the legendary improv and sketch comedy theater that has launched the careers of many famous comedians. Visitors can immerse themselves in the local arts scene by attending a performance or simply enjoying the vibrant street art that adorns the neighborhood. Old Town also boasts a variety of dining options, from upscale restaurants to casual eateries, offering a taste of Chicago's diverse culinary landscape. Don't miss the chance to explore the charming parks and outdoor spaces, perfect for relaxing or enjoying a picnic. With its lively atmosphere and historical significance, Old Town provides a unique experience that captures the essence of Chicago, making it an ideal destination for tourists looking to explore the city's cultural richness.