The South Loop neighborhood is a perfect blend of livability and entertainment, housing many of Chicago’s most iconic spots. Located right in the heart of the city, South Loop offers amazing sights, delectable restaurants, and some of the best bars in the city. Whether you’ve lived in the neighborhood for years or just plan to visit, head to one of these popular South Loop bars to round out your evening.
If you want to make this neighborhood your next home, reach out to AptAmigo, and we’ll help you find the perfect apartment. If you’re still searching for a neighborhood that is right for you, read our ultimate Chicago neighborhood guide.
Apartment Spotlight: The Saint Grand
The Best South Loop Bars
Brando’s Speakeasy
Located: 343 S Dearborn St, Chicago, IL 60604
Voted Chicago’s #1 karaoke bar, people flock to Brando’s to sing Mariah Carey chart-toppers until 2 AM. Enjoy a glass of champagne and a charcuterie board while you listen to the Windy City’s best shower singers.
Or, grab one or two of their specialty martinis and belt out some tunes yourself. With a classic speakeasy vibe and an extensive cocktail list, you can’t really argue with their tried and true slogan: “Dance. Drink. Sing.”
Our favorite drink:
Martini #5, which features a flora hemp spirit and a guaranteed good time.
VU Rooftop Bar
Located: 133 E Cermak Rd, Chicago, IL 60616
If a mood for a classy cocktail and a sleek ambiance 22 stories above ground strikes you, head to VU Rooftop Bar. With 13,000 square feet of breathtaking lakeside views, this rooftop bar offers an experience unlike any other. Whether you go for a quick drink or plan to feast on their locally sourced food menu, VU will not disappoint.
Their “Large Format” cocktails cater to big parties, so check them out next time your friends are looking for an upscale evening. VU also regularly hosts events, ranging from a cocktail competition to a catered cardio dance class.
Our favorite drink:
“Lakefront Property,” with a base of blue shimmering wine from August Hill Winery, a truly mesmerizing beverage in a stunning space.
Reggies Trainwreck Rooftop Deck Bar
Located: 2109 S State St, Chicago, IL 60616
This spot offers free trivia, an extensive brew list, and live music, all under one roof. With propane heaters in the winter and a pull string shower for the sweltering summers, Reggies is an all-season hit. And that includes baseball season. Their rock ‘n’ roll bus transports patrons to and from Sox games.
Whether you prefer fruity or hoppy, a rich selection of local beers provides a flavor you’ll love. Ultimately, Reggies serves straightforward drinks in a friendly and casual setting ideal for meeting new people.
Our favorite drink:
A pint of beer from Goose Island Brewing or Lo Rez Brewing, both of which are local and delicious.
Weather Mark Tavern
Located: 1503 S Michigan Ave, Chicago, IL 60605
Located a short walk away from both the Field Museum and Soldier Field, Weather Mark Tavern sits right in the heart of the city. Considered one of the best nautical-themed bars in Chicago, it’s a great spot to visit after a day spent on the water. This family-run bar serves a wide variety of drinks and bites, and it boasts one of the biggest rum selections in Chicago, with over 50 bottles.
Whether you are a sailor, a rum connoisseur, or a new transplant to Chicago, everyone has a seat at Weather Mark Tavern.
Our favorite drink:
Celebrate your lakeside life by indulging in their rum old fashioned, featuring Dictador 12-year rum.
Half Sour
Located: 755 S Clark St, Chicago, IL 60605
Stop in for a spectacular brunch or an afternoon delight. This modern, chef-driven spot sells American deli fare and refreshing beverages. Although Half Sour remains open for dinner as well, get there before 2pm to catch their stellar brunch menu, full of morning drinks that’ll start your weekend off right. With an extensive beer, wine, and cocktail menu, you can truly “pick your poison” here.
Fun Fact: This fabulous space got its name from a type of pickle.
Our favorite drink:
We highly recommend their Bloody Mary, which is garnished with a half sour pickle.
Find your Dream Chicago Apartment
Now that you know the best spots to grab a drink, you’re ready to find your new place. Reach out to AptAmigo, and we’ll pair you with a dedicated apartment expert who will do all the hard work for you. With our local insight, apartment expertise, and access to the best deals on the market, apartment hunting has never been easier. The best part? It’s 100% free!
* The original version of this article was first published on November 23, 2020.
Rebecca is a freelance writer over a decade of journalism experience. She graduated with a BA in Communications and a minor in journalism. She currently bartends in downtown Chicago and spends her free time exploring the city and making connections.
