10 Bucket List Things to See and Do in the South Loop

The South Loop is an area steeped in history — while always evolving and adapting for the future. Sometimes known as Chicago’s “front yard,” the South Loop has been a major shipping and transportation hub, and was the epicenter of the Midwest’s printing industry up until the 1960s. It was also the home of some of Chicago’s most famous families throughout the early 19th century. 

Today, the South Loop is a lovely and mellow area, full of great restaurants, incredible music venues, lots of parks, and some of Chicagoland’s most famous museums and tourist destinations. 

So, what should be on your “bucket list” of things to see and do in the South Loop? Here are ten amazing South Loop experiences not to be missed: 

Learn and Explore on Museum Campus

Museum Campus is one of Chicago’s crown jewels. This sprawling area is home to some of the Midwest’s most famous museums and cultural institutions. For anyone who wants to learn more about the universe with fun, hands-on exhibitions and shows, Adler Planetarium is a must-see. Shedd Aquarium is a great place to learn more about the fascinating animals and plants that call our lakes and oceans home. Meanwhile, the Field Museum is a Chicago icon, as its centerpiece exhibition, Sue the T-Rex. On top of its unique cultural offerings, Museum Campus offers some lovely greenspaces, and breathtaking views of the Chicago skyline and Lake Michigan. 

Jam Out at Some of Chicago’s Most Unique Music Venues

The South Loop is one of Chicagoland’s best neighborhoods for music lovers. Buddy Guy’s Legends is a classic place to take in some Chicago-style blues, as is Willie Dixon’s Blues Heaven Foundation — a museum dedicated to the sounds and history of Chess Records, a historic Chicago record label. Not too far away, Reggie’s is a go-to spot for punk, metal, and alternative fans. Since 1947, Jazz Showcase has been one of the region’s best spots for live jazz music. And Huntington Bank Pavilion at Northerly Island is a huge outdoor venue that houses some of the biggest names in music when they pass through Chicagoland. 

Enjoy a Nature-Filled Oasis in the City

Don’t let its proximity to downtown fool you! Whenever you’re ready for a break from the hustle and bustle of the city, the South Loop is full of spots to escape into nature. Just south of the rolling green lawns of Museum Campus you’ll find Northerly Island Park. This 119-acre natural area features strolling paths that lead you through prairie grasslands, fishing ponds, and more than 150 different varieties of native plants. Tucked in a quiet corner of the South Loop neighborhood is the Chicago Women’s Park and Gardens, a 3.23-acre park which honors the contributions women have made to Chicago throughout its history. Opened in 2000, this serene area offers a community garden and gorgeous, landscaped grounds. 

Cheer the Home Team at a South Loop Stadium

There aren’t too many Chicagoland destinations more iconic than Soldier Field. Located in the heart of the South Loop, this legendary stadium is home turf for the Chicago Bears, and recently became the home base of Chicago Fire FC, the city’s MLS soccer team. Soldier Field also hosts concerts, live performances, and charity events throughout the year. Nearby, basketball fans line up for incredible indoor action at Wintrust Arena, which houses DePaul University’s basketball programs, as well as the Chicago Sky, the city’s dominant WNBA team. 

Sample One of the South Loop’s Legendary Festivals

The South Loop puts you close to some of Chicago’s liveliest local festivals and outdoor events, including Printers Row Lit Fest and Printers Row Art Fest, which set up shop in one of the South Loop’s coziest and most historic districts each year. Spend a summer day in the South Loop, and you’ll also be in a prime spot for one of Grant Park’s many seasonal festivals, including Taste of Chicago, Lollapalooza, and the Chicago Blues Festival, to name just a few. 

Roam Grant Park

Stretching along the easter edge of the city, Grant Park is one of Chicago’s most historic and iconic offerings. This sprawling park offers countless attractions and sights, including the world-famous Buckingham Fountain. Grant Park is also home to a Bark Park perfect for letting your furry friends run free, along with a skate plaza that welcomes anyone with a passion for boarding. Meanwhile, look out for incredible views of Lake Michigan from Queen’s Landing, or lounge out in the grass at Hutchinson Field. To the north, Grant Park also feeds into Millennium Park, home to the Art Institute of Chicago and Cloud Gate, one of the area’s most Instagram-worthy sculptures. 

Experience Some of Chicago’s Best Bars and Breweries

From the era of Prohibition to today, the South Loop has long been one of Chicagoland’s favorite spots for grabbing a drink. Today, the South Loop is one of Chicago’s liveliest areas for nightlife, home to restaurants and bars for every taste. If you’re looking to explore Chicago’s world-famous craft beer scene, you may want to pay a visit to Moody Tongue Brewing or Motor Row Brewery. Acadia is a local favorite for innovative cocktails, while First Draft is a go-to hangout for serious beer lovers. 

Step Back In Time In the Prairie Avenue Historic District

Before the Gold Coast became the name for old world Chicago opulence, the city’s wealthiest residents set up shop along Prairie Avenue. Sometimes known as Millionaire’s Row, the Prairie Avenue Historic District is a local and national landmark, and is a living monument to the architectural wonders of the 1800s. Today, several of this area’s most iconic dwellings have become museums, including the John J. Glessner House and the Henry B. Clarke House, which is Chicago’s oldest surviving residence. Several other Prairie Avenue manors have been converted for new purposes, including the Wheeler Mansion —  now a boutique hotel — and the Marshall Fields house, which has been converted into condos.  

Start the Day With Brunch

Aficionados of all things breakfast are sure to enjoy a trip to the South Loop, which is home to plenty of popular spots for enjoying the most important meal of the day. For a sweet treat, you could start your morning at Stan’s Donuts & Coffee, or pop into Chicago Waffles for a full-service brunch. The Spoke & Bird is a popular cafe and restaurant with a variety of breakfast and lunch options. Eleven City Diner offers the charms of New York-style deli in a cavernous space, while Meli Cafe and Little Branch Cafe serve up classic breakfast favorites with a side of Chicago charm. 

Find a Local Treasure at a South Loop Shop

Full of unique stores and boutiques, the South Loop is a great spot for window shopping. Sandmeyer’s Bookstore pays tribute to the neighborhood’s literary heritage, while yarnify! and Artist & Craftsman Supply are popular destinations for Chicagoland’s creative crafters and makers. Jugrnaut is a local hotspot for Chicago-style streetwear and apparel, while Roosevelt Collection is a beautiful open air shopping complex featuring local shops and high end national chains. 

Want to Keep Exploring the South Loop?

Want to get to know this active and energetic Chicagoland community even better? To see market trends, properties for sale, and more, please visit our guide to South Loop real estate, available here.

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