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Self-Guided Chicago Walking Tours

Updated: April 21, 2023
 By Mel

We are happy to have produced several self-guided Chicago walking tours and our collection is growing.

We designed these self-guided tours to be used on your own time and at your own pace or as companion pieces on our guided tours. Some tours are only available as self-guided tours.

Self-Guided Chicago:

Please do consider our guided walking tours as well.


Chicago is full of various districts and neighborhoods that each have their own personality and attractions.

Here are several self-guided tours that focus on specific areas of the city.

The Navy Pier

One of the most popular stops for visitors of Chicago is the south dock of Navy Pier, a 2,000-foot-long pedestrian boardwalk that stands as one of the best in the United States.

With entertainment venues, restaurants, and theme park rides, Navy Pier is open year-round for your enjoyment.

Take this self-guided walking tour to experience the best of the boardwalk!

Wicker Park

Experience Wicker Park like a local with this self-guided walking tour!

Learn the history and experience the cultural highlights through a 1.8-mile walk around Chicago’s trendiest neighborhood.

With over 150 restaurants and a bustling shopping scene, Wicker Park is a welcoming place to shop and indulge with a rich history to pull it all together!

There are many things to see in Wicker Park.

Millennium Park

Millennium Park was revealed in 2004 after Mayor Richard M. Daley’s plan to convert the then unsightly industrial wasteland into a 25-acre park filled with architecture, sculpture, and flora.

Large public events, many of which are free to the general public, are held each year in Wrigley Square and Jay Pritzker Pavilion.

Keep your cash and enjoy the beautiful Millennium Park, an absolute must-see when visiting Downtown Chicago.

Popular for its variety of visual, performance, and agricultural artwork, Millennium Park is a frequent spot for locals and visitors.

Downtown Theater District

This tour explores the Downtown Theater District and the gorgeous architecture of the old movie palaces and concert venues.

There are many other gorgeous theater buildings and incredible theater companies in other areas of Chicago.


The Chicago neighborhood known as Wrigleyville is not only the home of the Chicago Cubs but also a fun and vibrant area filled with many bars, restaurants, sports stores, and more!

Located about 5 miles north of The Loop, Wrigleyville is part of the central Lakeview neighborhood and is named for historic Wrigley Field which, when built in 1914, drew thousands of people to the area.

This self-guided tour takes you 1.3 miles north along North Clark Street and includes 10 stops, but be sure to enjoy all that this neighborhood has to offer!


If you're looking for more than history and picturesque sights, consider taking a food tour.

One of the best ways to learn about an area's culture is by sampling the traditional dishes!

Chinatown Food and History Tour

The Chinatown Food and History Tour is a delicious and interesting walk.

Set amongst the backdrop of cultural landmarks and popular sights such as the Nine Dragon Wall, Chinatown Gate, and Ping Tom Memorial Park, Chinatown offers a glimpse into the customs, traditions, and rich culture of one of the oldest civilizations in the world.

Pilsen Mexican Food Tour

The Pilsen Mexican Food Tour celebrates the Mexican culture that runs strong and deep in Chicago.

One of the best places to experience Mexican culture and cuisine is with a walk to sample Mexican specialties including tamales, tacos, carnitas, churros, pastries, and so much more.

Anderson Food Tour

On the Andersonville Food Tour, you’ll not only get a taste of authentic Swedish eats but also see how diverse it has become with the addition of Middle Eastern, Italian, and Belgian flavors to the neighborhood.

Andersonville has an evident sweet tooth, with cafes dedicated to service pies, ice creams, and every kind of candy imaginable!

Little Italy Food Tour

Little Italy, sometimes called University Village, is a neighborhood on the Near West side of Chicago, just between the University of Illinois at Chicago (UIC) campus and the Illinois Medical District.

The Little Italy Food Tour focuses on the district's culture as well as the delicious food.

Its Italian-American heritage is primarily evident in the Italian-American restaurants of Taylor Street.

The neighborhood is home to the National Italian American Sports Hall of Fame as well as the historic Roman Catholic churches (Our Lady of Pompeii, Notre Dame de Chicago, and Holy Family).

Greektown Food Tour

The Greektown Food Tour shows off a diverse and urban neighborhood; professionals, families, Greeks, and non-Greeks all co-exist.

Yet despite the diversity of the inhabitants, living in Greektown lends itself to participating in Greek culture.

The area celebrates its Greek identity constantly; restaurants display bright Greek flags, signs are in Greek as well as in English, and many buildings, reminiscent of Greece itself, are painted pure white.

On this tour, you’ll get a taste of the Greek culture and we’ll help navigate you through the Greektown strip of South Halsted Street.


Below we have listed not-quite-walking tours.

Chicago Biking past the Shedd Aquarium with the Lake on your right Chicago Bike Tour

Hop on a bike and explore more of what Chicago has to offer in a short time frame by getting some exercise on a Chicago Bike Tour.


About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: April 21st, 2023
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