Top Picks For You
Chicago Travel Guide

Don’t Listen to People Who Tell You Not to Go to Chicago’s South Side. Visit These 10 Must-See Spots

The South Side of Chicago isn’t the “danger zone” many have painted it out to be. It’s full of hardworking people, rich history, and awesome restaurants.

When tourists inquire about visiting Chicago, they’re almost always met with warnings and negative connotations about the South Side of the city. Many of these neighborhoods are only recognized when tragedy is in the headline, prompting conversations that begin with “Don’t go there! It isn’t safe.” But Chicago’s allure stretches farther than Millennium Park and its fancy Lake Shore Drive highrises.

I think that now is as good a time as any to talk about how the South Side is the flavor in the melting pot of Chicago. Here are some must-see spots that are sure to spice up your next Windy City visit.

1 OF 10

Old Fashioned Donuts

WHERE: 11248 S. Michigan Ave.

Mouth-watering apple fritters, cinnamon swirl donuts, and the glazed—a fan favorite–are just a few of the items that “Mr. B” has been serving up for visitors at Old Fashioned Donuts in the Roseland neighborhood for nearly 50 years. If you happen to run across a “Best Donuts in Chicago” list and this place isn’t on it, trust me when I say, that list isn’t legit. The owner says that he can attribute his longevity to quality products and adding a lot of love to the dough. People in the community have taken pride in helping to keep this small business up and running over the years. No matter what part of the city you’re from, these sweet treats are worth the drive.

2 OF 10

DuSable Museum

WHERE: 740 E. 56th Place

Since 1961, this museum has been a beacon in the community and dedicates itself to the conservation of African American art, culture, and history. From elaborate exhibits to unique artifacts and artwork, the DuSable Museum has played a vital role to both tourists and Chicago natives through their legacy of pushing the message of Black resilience, strength, and beauty to the forefront. From educational displays that include the Civil Rights Movement of freedom and equality to art that showcases the contributions of Chicagoans like Margaret T. Burroughs and her legacy—this place is perfect and highly recommended for families and children. It is a unique educational experience.

3 OF 10

5 Loaves Eatery

WHERE: 405 E. 75th Street

An unassuming establishment with no bells and whistles, 5 Loaves Eatery has a walk-up window for takeout orders and just a handful of tables and chairs for its dine-in patrons—but it serves up some of the best soul food dishes around, from shrimp and grits and fried chicken to lemon zest pancakes with homemade buttermilk syrup. Be sure to wash down your meal with their popular Arnold Palmer (which consists of sweet tea and lemonade served in a mason jar). The owners opened 5 Loaves Eatery over 16 years ago because they were tired of taking their family outside of the neighborhood to get quality meals. They’ve since drawn a huge following that consists of everyone from local congressmen to TV personalities.

4 OF 10

Michelle Obama’s Family Home

WHERE: 7436 S. Euclid Ave.

Visitors from all over the world flock to the former first family’s home at 5046 S. Greenwood Ave. in Hyde Park. But few talk about the 1920s bungalow where a young Michelle Robinson lived with her family in the South Shore neighborhood. Her parents rented the upstairs from her great-aunt who lived on the first floor. In her best-selling book Becoming, Mrs. Obama gives readers a glimpse into her memories of growing up on the South Side of Chicago and her humble beginnings before the success and the road to the White House.

5 OF 10

14 Parish

WHERE: 1644 E. 53rd Street

If you can’t make it to the Caribbean, this place is the perfect staycation experience. With over 100 different kinds of rum in its repertoire, 14 Parish creates tropical cocktails and tantalizing dishes that’ll make you feel as though your passport has already been stamped. Dishes like the deliciously tender sweet and spicy short ribs with cabbage and corn muffins, coconut curry shrimp, and the jerked catfish are just a few of the menu highlights. Finish your dining experience with the popular “Parish Punch”, made with Wray & Nephew, dark rum, pomegranate juice, and lime and your night is set. Ya Mon!

6 OF 10

Fountain of Time

WHERE: 6000 S. Cottage Grove

Located in Washington Park and installed in 1922, the Chicago Park District calls the Fountain of Time one of the most significant historic works of art in the city. Sculptor Lorado Taft spent over a decade creating the masterpiece after becoming inspired by the poem The Paradox of Time, written by Henry Austin Dobson. The sculpture depicts 100 human figures—all different ages—from infants to soldiers. They’re all being watched over by a “Father Time” figure, reminding us not only of how quickly the years go by but serving as a memorial of the first 100 years of peace between Great Britain and the U.S. following the war of 1812.

7 OF 10

Home of The Hoagy

WHERE: 1316 W. 111th Street

Home of the Hoagy has been a staple in the Morgan Park neighborhood since 1969. The original building was destroyed by a fire in 2015, but the owners didn’t let that setback stop them from serving the community. They picked up the pieces, moved into the building next door, and continued to dish up some of the same hoagies that have had customers standing in long lines for over 50 years. The turkey hoagie–with cheese, onions, tomatoes, pickles, banana peppers, and lots of oil and vinegar–is a delicious treat. But the steak hoagie served “sweet-hot” (which refers to the sweet and hot peppers applied to the sandwich) is the perfect mix of greasy and delicious, your waistline might hate it but that your tastebuds will thank you for it.

8 OF 10

Pullman National Monument

WHERE: 11141 S. Cottage Grove Ave.

The Pullman National Monument was created to act as a worker’s facility center of the Pullman Palace Car Company. The Pullman Palace Company hired African American men (many of them former slaves) in the late 1800s and early 1900s to work in service positions along the rail lines created by engineer George Pullman. The Pullman Porters eventually played a pivotal role in the labor and civil rights movement and the great migration. The district is known for being an industrial hub and, in its early days, many working-class people lived in and took advantage of the job opportunities, beautiful architecture, and safe conditions that this area provided to families in the 20th century. It was designated a national monument in 2015 by President Barack Obama.

9 OF 10

Can’t Believe It’s Not Meat

WHERE: 1368 ½ E. 53rd Street

Whether you’re vegetarian or what the owners like to call “flexitarian” (transitioning to a plant-based diet), meatless options of some of your favorite comfort foods can be found at Can’t Believe It’s Not Meat in the Hyde Park neighborhood. Dishes like “Little Italy Lasagna”, “Bucktown Bratwurst,” and the “Triple Decker Vegan Turkey Sammich” are all delicious alternatives to those who are looking for healthier ways to indulge. They also offer delicious smoothies and vegan shakes, like their decadent “cookie monster” (which is their take on a cookies and cream milkshake) prepared with soy ice cream and almond milk.

10 OF 10

Brown Sugar Bakery

WHERE: 328 E. 75th Street

This place has received accolades for its delicious baked goods and, specifically, its one-of-a-kind caramel cake, praised by Chicago Mayor Lori Lightfoot, Vice President Kamala Harris, and Lt. Governor Juliana Stratton. Stephanie Hart, the owner, opened Brown Sugar Bakery in the Chatham neighborhood in 2004 and, despite its struggles, Hart remains the “cake queen” of the South Side. Serving up traditional German chocolate and red velvet cakes to more unique delectables like turtle and Neapolitan, this bakery not only provides the community with out-of-this-world desserts, but also assists women who have survived domestic violence situations by donating shoes, clothes, and hygiene products collected from the community.