Five Chicago Self-Guided Walking Tours

1. Andersonville

Set on a one-mile strip on North Clark Street, Andersonville houses a wide array of restaurants, shopping, vintage goods, and more.  This 'hood is rooted in Swedish culture and mixes old European charm with modern Chicago. 

Begin your stroll at Foster Avenue and N. Clark Street and have your little ones look up. You’ll see Andersonville’s iconic neighborhood symbol: a large, blue-and-yellow-painted water tower, reminiscent of the Swedish flag. If you’re feeling historical and have the time, the Swedish American Museum offers kid-friendly exhibits and a gift shop.

From the museum, continue north along Clark until you hit the first stop sign, then cross the street and head into Women and Children’s First Bookstore.  Here, you can find modern-day titles, children's books, and unique gifts. As you amble north, you’ll want to cross the street to head into Jeni’s Ice Cream for a quick treat for all. 

Post-snack, look for various shops, including children’s clothing, toy stores, curated antiques, and other finds, via a large Brown Elephant housed in an old live theater space. Kids will love running up and down the ramp and exploring the unique space while you shop the shelves for yourself.

As hunger levels start to bubble, hit Pizza Lobo, a casual indoor and outdoor NYC-style pizza joint, and wind down with their bocce ball courts and communal fire pits.

 
Robie House photo by Warren LeMay via Flickr 2.0

2. Hyde Park 

Home to one of Frank Lloyd Wright’s more famous homes (and Ultimate Illinois Bucketlist item!), the Robie House, your strolling tour starts here. 

If your children are old enough to appreciate architecture or at least cool homes, grab your tickets and head inside for a historical tour of some of mid-century modern’s finest work. If not, the surrounding area boasts plenty of green space for younger ones to run while you take in your history from the outside. 

After your introduction to the neighborhood, you’ll want to head north two blocks and then west for a quick nosh at Medicis on 57th, a long-standing sandwich shop that caters to college students and past presidents alike. 

Head west about 10 minutes on foot until you reach Jackson Park. Depending on the time of year, typically during spring, you can catch the blooming cherry blossoms.

Next, finish your day at the Griffin Museum of Science and Industry—it’s huge and packed with immersive exhibits, like walking onto a real suspended airplane, watching baby chicks hatch, and standing eye-level with a giant U-505 submarine. You'll want to read our Griffin Museum Guide to get the most out of your time there. 

The museum offers snacks inside, like donuts from Stan’s Donuts, but if you’re hoping for a more substantial bite at the end of your tour, you can hop a bus or car and head eight minutes north to Daisy’s Po Boy and Tavern, a casual, cajun-style eatery.

Peggy Notebaert Nature Museum photo by Kevin Chang via Flickr 2.0

3. Lincoln Park

Perhaps one of the best-known neighborhoods and parks in the city, Lincoln Park is home to a zoo, a nature center, a petting zoo, a conservatory, a seasonal lily pond, walking paths, and many other attractions. If you're spending time in Lincoln Park, check out all the Best Things to Do in Lincoln Park with Kids for more.

Begin your journey at the Peggy Notebaert Nature Museum, one of our favorite Chicago museums, where tickets are relatively inexpensive for both residents and non-residents. Your little ones will love the interactive water exhibits, which feature plants and animals native to the Great Lakes. 

Depending on your children's stamina, a quick jaunt across the street includes the Lincoln Park Conservatory and Zoo, both of which are free to the public. The botanical garden allows you to BYOF, as does the zoo. However, if you forget, the zoo offers quick stops for snacks. For something more substantial, Café Brauer provides a variety of dishes, including salads, burgers, tacos, and more. Finish your tour directly south at the Lincoln Park ‘Farm-in-the-Zoo,’ which houses cows, rabbits, pigs, ponies, goats, and chickens. Read more tips on Lincoln Park Zoo here.

After visiting the nature center, botanical garden, or zoo, feed those rumbling tummies at R.J. Grunts. Home to one of the first salad bars in the city, the older ones in your group will love picking out their buffet selections, while typical American fare will cater to all.

4. Pilsen

Rooted in vibrant Mexican culture, Pilsen blends its Latin heritage with old-school Chicago. Start your walk at the 18th Street CTA stop, and head west. 

This self-guided tour features an outdoor history lesson, with vibrant murals lining the trees and buildings of Pilsen. The first mural you’ll see is the All About the Women piece, which features famous women in Latino culture.  

If your family is up for more history, head around the corner to 19th Street and visit the National Museum of Mexican Art, one of our favorite Free Museums in Chicago, with rotating exhibits and art classes for both kids and adults.

Head back to 18th Street and continue, stopping into the various vintage stores before you find yourself at Rubi’s Tacos. This taco joint specializes in homemade tortillas, fresh Jamaica juice, and authentic asada and al pastor tacos. 

Let your kids burn off some steam, or tacos, at nearby Throop Park, which features a playground and a water spray feature that operates during the summer months. 

5. Irving Park

Take a city reprieve in the Irving Park neighborhood, near Roscoe Village, but specifically located along the east side of Horner Park. Before you begin, you’ll want to satisfy any sweet tooth with a visit to Lutz Bakery. This bakery dates back to 1948 and specializes in buttery cakes and velvet frosting. 

Once you’ve all had your fill of baked goods, head to the north end of the park near Montrose Avenue and start your walk at the beginning of the natural wildlife area. 

This nature area boasts sustainability efforts and local wildlife and can be a fun spot for your little one to forage for a wildflower bouquet or try their hand at birding. 

A nearby playground with fun additions, such as a zipline, is just a short distance from the main trails. After the kids tire out, head west across the Irving Park bridge to Burning Bush Brewery. This brewery prides itself on being family-friendly and sells quick snack food items geared toward youngsters.