Chicago Old Town Walking Tour, Chicago

Chicago Old Town Walking Tour (Self Guided), Chicago

Settled in 1850 by German immigrants, Chicago’s Old Town neighborhood is a popular destination for locals and visitors who cater to the entertainment venues, restaurants, pubs, coffee shops and boutiques – all of which have turned an area once referred to as the “Cabbage Patch” into an attraction that rivals Navy Pier, Wrigley Field and the Magnificent Mile.

Start your Old Town walking tour with a stroll down Wells Street for dining and entertainment, then make a turn towards the architecturally and culturally significant West Burton Place to see how artists and craftspeople of the Depression Era transformed what were then deteriorating 19th-century rooming houses into a series of unique and cohesive artist studio environments.

Next up is the excellent Chicago History Museum’s coverage of all aspects of the city’s history, starting with a model of a fort and expanding into modern territory (including insights into Chicago’s leading role in innovations and design), while right opposite stands the Second City Theatre – a place that launched the career of many great comics, and that remains rooted in improvisational games you can experience today.

Further along the way, don’t miss a visit to St. Michael’s Church and the close-by Midwest Buddhist Temple (a fixture in Old Town since 1944), both located in beautiful green and quiet surroundings.

Take a self-guided walk through this clean and safe neighborhood to fully understand Chicago as a city!
How it works: Download the app "GPSmyCity: Walks in 1K+ Cities" from Apple App Store or Google Play Store to your mobile phone or tablet. The app turns your mobile device into a personal tour guide and its built-in GPS navigation functions guide you from one tour stop to next. The app works offline, so no data plan is needed when traveling abroad.

Download The GPSmyCity App

Chicago Old Town Walking Tour Map

Map Instructions: (1) Click the "Nearby Sights" button to view the nearby attractions; (2) click a map pin to see sight information.

Guide Name: Chicago Old Town Walking Tour
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles

Sights Featured in This Walk

WalkBuilder (customize this walk or build your own)


Use the WalkBuilder tool below to customize this walk to suit your interests. Instructions: click at the upper right corner in the map above to view other sights in the city. To learn more about a sight, click a map pin. Click the “+” or “–” to add or remove a sight from the walk. To reorder the selected sights, simply drag and move them up or down the list in the left column.
Click here to view route map
Enter a name for your custom walk, along with your email address, in the fields below. You will receive the instructions for retrieving your custom walk in the GPSmyCity app by email. The GPSmyCity app offers turn-by-turn travel directions to guide you from one attraction to the next.
Walk Name*:
Email*:

Frequently Asked Questions


1. How do I access my walking tour in Chicago?
Save your walking tour on the website. Then download the GPSmyCity app from the Apple App Store or Google Play Store and sign in to your GPSmyCity account. Next, download “Chicago Map and Walking Tours” within the app. Your walk will appear on the Walks screen.

2. How do I view other attractions in Chicago?
At the upper-right corner of the map above, click the “Nearby Sights” button to show or hide other sights in the city. Click a map pin to view details about a sight. To add a sight to your walk, find it in the right column of the WalkBuilder tool above and click the “+” button next to it.

3. How do I re-arrange the sight order?
In the left column of the WalkBuilder tool, drag a sight to move it up or down the list. Then click “Click here to view route map”. Repeat this process until the route meets your needs.

4. Can I add my hotel to a walking tour?
Yes. You can add your hotel as the starting point, the ending point, or both (creating a loop route). This feature is currently available only in the GPSmyCity app.

5. Can I add my own sights to a walking tour?
Yes. You can add sightss that are not in our database and include them in your walk. To do so, sign in to your GPSmyCity account on the website or use the GPSmyCity app.

6. How many sights can be included in a walking tour?
For technical reasons, the number of sights in a walking tour is currently capped at 20. This limit may be increased over time.

Walking Tours in Chicago, Illinois

Create Your Own Walk in Chicago

Create Your Own Walk in Chicago

Creating your own self-guided walk in Chicago is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Chicago Introduction Walking Tour

Chicago Introduction Walking Tour

Chicago, perched on the shores of Lake Michigan in Illinois, is a city steeped in history and urban vibrancy. Known by numerous nicknames such as the Windy City and the City of Big Shoulders, it boasts a skyline marked by towering structures. The area of today's Chicago, initially inhabited by Native American tribes, saw its first European-settled reference as "Chicagou" in 1679, a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.9 Km or 2.4 Miles
The Magnificent Mile Walking Tour

The Magnificent Mile Walking Tour

The stretch of Michigan Avenue from the Chicago River to Lake Shore Drive, otherwise known as the Magnificent Mile, is regarded as one of the world’s great avenues – or Chicago’s version of Fifth Avenue. Take this self-guided walk to explore its whole stretch and surrounding area, featuring a wide selection of amazing stores/malls, world-known museums, restaurants and spectacular...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 4.0 Km or 2.5 Miles
University of Chicago Walking Tour

University of Chicago Walking Tour

Founded in 1890, the University of Chicago is among the world’s most prestigious educational institutions. As of 2020, the University’s students, faculty and staff have included 100 Nobel laureates, giving it the fourth-most affiliated Nobel laureates of any university.

Set in the heart of Chicago’s famous eclectic neighborhood, Hyde Park, the campus is worth a visit as it offers a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.5 Km or 1.6 Miles
Chicago Navy Pier Walking Tour

Chicago Navy Pier Walking Tour

Additional to scenic views of the lake, the boats, and the city skyline, the Navy Pier offers a variety of attractions on the waterfront – for kids as well as adults – that draw nearly ten million people annually, making this Chicago's most visited spot. Yes, some may see it as a “tourist trap”, but it is worth the time and money to spend some time here, so take this self-guided walk...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.0 Km or 0.6 Miles
Chicago Chinatown Walking Tour

Chicago Chinatown Walking Tour

Tucked away just south of the Loop, the Chinatown of Chicago was established in 1912 and is considered one of the best examples of American Chinatown. While it may be one of Chicago’s smallest neighborhoods geographically, it is big on character, colors, sights, sounds, and flavors. Here, you’ll find a wide range of unique boutiques, specialty shops, religious sights, authentic Chinese...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Frank Lloyd Wright Architecture Tour in Oak Park

Frank Lloyd Wright Architecture Tour in Oak Park

Oak Park, located in Cook County, Illinois, just outside Chicago, made history in 1889 when Frank Lloyd Wright, one of America's most renowned architects, and his wife settled there, leaving a profound impact on the area's appearance. This village boasts the highest concentration of Wright-crafted buildings in the world - over a dozen! - making it a pivotal destination for enthusiasts to...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.2 Km or 2 Miles

Useful Travel Guides for Planning Your Trip


Chicago Souvenirs: 15 Distinct Local Products to Bring Home

Chicago Souvenirs: 15 Distinct Local Products to Bring Home

One of the most fascinating cities in the U.S., if not the whole world, Chicago has no shortage of things closely associated with it, often due to their direct origin (blues, gangstership, etc.), so one might literally be spoiled for choice as to what to choose as a "piece" of Chicago to...