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Trekking Around Chicago’s South Side

By June 28, 2018May 23rd, 20193 Comments

There are so many sides to Chicago, literally and figuratively. The first time I traveled to the Windy City, I stuck to the downtown area. I was in awe of the green parks and stunning architecture. I gushed over the lion statues outside of the art institute. I took selfies in front of the shiny reflection of The Bean, and dined on deep-dish pizza.

selfie at The Bean downtown Chicago

Eventually, after a few visits, I ventured out to explore Al Capone’s old haunts, Wrigley Field and the adorable neighborhoods on the North Side.

But it was the South Side where my sister settled, and where I’ve spent most of my time. It may be deemed the most ‘dangerous’ part of the city, but it’s filled with some amazing places. Her Hyde Park apartment overlooks Lake Michigan, and the University of Chicago isn’t far off. The area is also filled with educational museums, cozy restaurants and beautiful views.

Lake Michigan South Side Chicago

So next time you head to Chicago, don’t count the South Side out.

The Heart of the South Side

While the South Side is special in many ways, it’s Hyde Park that really stands out. Tree-lined streets, brick buildings, hip eateries and large train cars fill this area, which is always brimming with people. As you wander the streets, you’ll get a little bit of a Brooklyn vibe. There’s a definite grit to the South Side that gives it character.

Hyde Park Chicago

Taking a walk is one of the most magical things to do here. Giant, shady trees tower over the narrow streets while colorful flowers bloom in the spring and summer. Children delight over the fun to be had in neighborhood playgrounds. There’s something quaint about the storefronts and eateries.

Rockefeller Chapel University of Chicago

Heading over toward the college, you’ll find some beautiful stone chapels and cathedrals with stained glass windows. Another notable spot on campus is the law school’s reflecting pool while history buffs will get a thrill visiting former President Barack Obama’s favorite classroom from his teaching days. His family home is located just a mile north of the school.

A Lot to Learn

One of Chicago’s finest attributes is its many museums. While most are located downtown, the South Side is home to one of the best: Museum of Science and Industry. The many hands-on exhibits may be aimed towards children, but that won’t stop adults of all ages from learning too. My favorite exhibits touched on everything from storms to baby chicks to World War II submarines and robotic assembly lines. The 14-acre building is impressive itself, built in a Neo-Classical style with large columns and intricate carvings.

While the science museum is a highlight of a visit to the South Side, there are others to consider too. Between downtown and the South Side, you’ll find Museum Campus. This spot is home to a natural history museum, an aquarium and a planetarium.

Field Museum dinosaur Chicago

At the Field Museum, see everything from dinosaur bones to ancient Egyptian tombs and displays of Native American culture. The Shedd Aquarium, on the other hand, gives visitors a chance to get a close-up look of penguins, jellyfish, seahorses, sharks and more. Or visit the Adler Planetarium to check out exhibits about the solar system and space exploration as well as sky shows in the dome.

South Side Eats

Start your morning at one of a few different spots; there are numerous breakfast eateries worth visiting in Chicago’s South Side. From Obama’s favorite, Valois Restaurant, which serves traditional breakfast foods counter-style all day long to Medici on 57th, which offers a warm, eclectic atmosphere. For something a little more trendy, order something off of the seasonal brunch menu at Chicago gastropub The Promontory.

The Promontory best breakfast in Chicago

By night, choose between Italian and Mexican. Nella Pizza e Pasta serves up utterly delicious Neapolitan fare. Because I went in a large group, we decided to order a bunch of different dishes to share. From the arugula salad with Parmesan and lemon juice to calamarata with calamari and red sauce as well as a sausage-filled pasta in a white cream sauce, everything we tasted was absolutely amazing. We also enjoyed two pizzas: the Nella D.O.P, with tomatoes and mozzarella, and one with prosciutto and arugula. They even served up Italian desserts, like cannoli and tiramisu.

If it’s killer margaritas, tacos and enchiladas you seek, Maravillas Restaurant is the place for your group. The eatery’s extensive menu is filled with delicious options that you can customize you create your ideal Mexican meal. And as someone that lives in Southern California—home to some of the best Mexican food—I can vouch for the deliciousness of this place. There is a dance floor with colorful lights and upbeat Latin tunes to keep your energy up too.

Along the Lakeshore

Lakeshore sunset Chicago

While it’s hard to escape the concrete sidewalks in the South Side, even with the many trees and flowers, there is one place to enjoy the great outdoors in the finest of ways. Head along the shore of Lake Michigan, where you’ll find a variety of spots to enjoy green expanses for picnics or barbecues, or concrete stairs on which to watch the sun go down. The sky will turn colors of pink and purple you’ve never seen before with the downtown skyline as the backdrop in the distance.

Staying in Chinatown

North of Hyde Park, Chinatown is also located in the city’s South Side, offering a wealth of culture to explore. You’ll find a variety of small shops and markets here in addition to the dim sum eateries and teahouses. Stop by the Chinatown Gate for a decorative welcome or stroll the area to take in sculptures, murals and Chinese-style architecture.

Chicago Hotel Jaslin viewChinatown also happens to make a great place to spend the night. Book a room at the Jaslin Hotel to be right in the heart of the action. Located across the street from the Chinatown Gate, the hotel has a sprawling view of the region with the downtown skyscrapers in the background.

Jaslin Hotel Chinatown Chicago

Though simple from the outside, the interior of the Jaslin offers a warm atmosphere, including rooms with plush beds and blackout curtains to keep the sun from waking you too early. Rooms with two beds can make it easy for groups to bunk together, but if you do have to split up, meet downstairs. The lobby has a beautiful fireplace and comfortable seating for you all to plan your adventures through the South Side together.

Trekking Chicago's South Side

Have you explored the South Side of Chicago? How did it compare to your experiences in downtown? What was your favorite place to visit on the South Side?

Ashley Ryan

Author Ashley Ryan

Ashley Ryan is a southern California native with a background in journalism and anthropology. She loves learning about other cultures and combines her passions for traveling, writing and photography in her professional work. To learn more or get in touch, visit

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