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What to Do in the Chicago South Loop

Street art in Chicago

Like many areas of Chicago, the South Loop has seen its ups and downs throughout the centuries. Lows like the Great Fire of Chicago are countered with highs like the printing heyday, the construction of the railroad, and modern-day re-development. The beautiful old buildings that housed the printing presses and railroad warehouses have been preserved and converted into fashionable lofts and apartments. The South Loop’s important location and role in Chicago’s history contribute to making it the vibrant and fascinating place that it is today. Despite being a popular residential area, its varied options for entertainment, eating, and landmarks make it a go-to destination for tourists too.

In every Chicago neighborhood guide, the South Loop is top for arts and entertainment, but there’s much more to this quirky area. Here is our guide of things to do in South Loop Chicago.


As well as streets steeped in history, the South Loop is home to some of Chicago’s best museums. The 57-acre Lakefront Museum Campus is definitely one of the jewels in our crown. Whether you’re looking to get out of the house on a rainy day or try something different in your own city, the three museums are varied enough to have something for every interest.

The Field Museum of Natural History is world-renowned for the quality of its permanent exhibitions and its sheer size — it’s one of the largest natural history museums in the world. If the world of Ancient Egypt fascinates you or you want to catch a glimpse of the world’s earliest fossils then step right in. Even when you can’t travel, you can still delve into the cultures of Tibet and China within the walls of this magical space.

If experiencing another culture isn’t enough, try experiencing a different galaxy! The Adler Planetarium offers thrilling virtual-reality experiences through time and space in their Sky Theater. Study different aspects of the solar system, learn how to stargaze, and find out about the importance of astronomy in culture. This museum is run by world-class researchers who want to share their knowledge.

Animal lovers can spend an afternoon at the Shedd Aquarium, you may have walked past it a hundred times and never entered this almost century-old marvel. Spot jellyfish and beluga whales, or bounce between continents with the Caribbean Reef and Polar Zone exhibits. It’s difficult to drag yourself away from the endless different species so try and keep the whole day free.

South Loop Chicago Restaurants

As the population grows, so does the restaurant scene down here in South Loop. Take your pick from flavorful street food or fine dining and everything in between. There are a variety of Spanish restaurants in the area but our stand-out favorite is Mercat a la Planxa. This Catalan restaurant will serve you up dishes like paella, gambas al ajillo, grilled octopus, croquetas, jamón Iberico, and burnt basque cheesecake. If that hasn’t got your taste buds tingling, check out their full menu, but don’t do it on an empty stomach!

One of our favorite spots for a bowl of pasta or an authentic Sicilian pizza is Pacino’s in South Delano Court. Fill up on a bowl of cacio e pepe or linguini alla vongole. Whether you’re after antipasti, pizza, or a steak, this restaurant provides an authentic Sicilian culinary experience.

For those looking to indulge in a special occasion, the Michelin-starred restaurant, Acadia, has put the South Loop dining scene on the map. The chef, Ryan McCaskey, rustles up dishes inspired by Maine and Vietnamese cuisine. Choose to sit at the bar and sample the à la carte menu, or take a seat in the dining room to embark on the seven-course tasting menu.

If you’re looking for the perfect afternoon itinerary in Chicago, why not combine one of our Chicago boat tours with a wood-fired pizza from Michelin-recommended restaurant, Sono. Sono is just around the corner from the River City Marina where the boat docks, making it the perfect spot to grab a post-ride bite.

Music & Entertainment

Here in the South Loop, we’re home to some of the oldest live music venues in Chicago.

The iconic Buddy Guy’s Legends is a go-to venue for blues fans. The club was founded by the legend himself Buddy Guy in 1989. The blues icon, at the age of 84, still regularly takes to the stage himself and the club is part of Guy’s quest to keep blues alive. Ranked as 23rd in Rolling Stone magazine’s ‘100 Greatest Guitarists of All Time’, Buddy has been an influence on stars such as Eric Clapton, Keith Richards, and Jimi Hendrix.

Jazz Showcase, having opened in 1947, is renowned for being the oldest jazz club in the city. Catch performances from internationally renowned musicians seven nights a week. With walls lined with photos of previous performers such as Duke Ellington and Dizzy Gillespie, it’s hard not to be in awe of the significant role this bar has played in the history of jazz.

If you’ve lived in the Chicago South Loop for a while but haven’t caught a ballet performance in the Auditorium Theater of Roosevelt University, it’s time to book a ticket for a night on those velvet-covered seats. Whether you choose to see a theatrical performance, see a touring ballet troupe’s work, or appreciate the spectacular architecture of the place on a Historic Theatre tour, this Historic Landmark should definitely be on your list of things to do in South Loop, Chicago.


An often unknown fact to South Loop residents is that the area was the original Gold Coast of Chicago. Wealthy residents set up homes in the area, building mansions, some of which still survive today. With the arrival of large volumes of traffic in the 20th century, and along with the installation of brothels and gambling houses, the richer residents moved out to what is now the Gold Coast. Due to this history, South Loop is home to some of the most spectacular architecture in the city.

Chicago’s oldest surviving house, Clarke House, built in 1837, has now been converted into a museum where visitors can see what life was like for a family before the Civil War. The Greek Revival-style mansion has been moved twice in its lifetime and now currently resides on South Indiana Avenue.

From traditional to groundbreaking, another must-see landmark is the Hilliard Tower Apartments. Designed by Bertrand Goldberg, the architect behind Marina City, the buildings were always designated to be part of the housing projects. Goldberg believed this type of social housing was often built without any attention to aesthetic detail and he designed the towers with the goal of providing structures that people would be proud of.

A great way to get a feel for Chicago architecture is to take a ride down the river. Here at Tours & Boats, we offer Chicago architecture sightseeing boat tours on all three branches of the Chicago River. We’ll point out hidden gems and give you entertaining and informative background on the spectacular structures on the Chicago skyline.

Hidden Gems

The South Loop itself is a hidden gem in the city of Chicago. Often praised for its oasis-like atmosphere and the lack of hustle and bustle compared to the surrounding neighborhoods, it’s no wonder that this area is at the top of many people’s desired places to live. As a resident or tourist, there’s a couple of places we consider hidden gems of the South Loop, but the top of the list is Printer’s Row.

Printer’s Row, which was once the home of the printing industry in Chicago, was injected with new life when the abandoned warehouses were converted into lofts and apartments. The historic buildings have been preserved and bookstores have now come to inhabit the spaces that were once used to print reading material. There’s nothing like strolling down Printer’s Row on a warm or rainy day and stopping by the quirky stores along the way to pick up a great book.

For art lovers on a tight budget, the Wabash Arts Corridor is a goldmine. A series of murals, street, performing, and media art centered around South Wabash Avenue was started as a movement to reclaim public spaces with art. The project was started by Colombia College Chicago in 2013 in a bid to transform urban life for residents and visitors through greater inclusion of art. Follow their map to see as many of the spectacular and thought-provoking murals that you can.

As a resident of South Loop, it’s easy to forget how much there is to do in the space around you. Try something different and start exploring your local area with as much interest as you would in a new city!

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