The South Loop neighborhood is a perfect blend of livability and entertainment, hosting 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 (River North has some great ones, too)! Whether you’ve lived in the neighborhood for years or you’re just visiting, these popular South Loop bars are a must-visit. 

If you feel like this neighborhood should be 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 here.

The Best South Loop Bars

Brando’s Speakeasy

Located: 343 S Dearborn St, Chicago, IL 60604

Voted as Chicago’s #1 karaoke bar, this spot is the perfect place 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 you’re in the mood for a classy cocktail and a sleek ambiance 22-stories above ground, head to VU Rooftop Bar. With 13,000 square feet of breathtaking lakeside views, this rooftop bar offers an experience unlike anything else. Whether you’re just going for a quick drink or planning to feast on their locally sourced food menu, VU will not disappoint.

Their “Large Format” cocktails cater to big parties, so be sure to 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. (Even 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 something for everyone. Ultimately, Reggies is a friendly and casual spot that offers straightforward drinks and a great opportunity to meet new people!

Our favorite drink: A pint of beer from Goose Island Brewing or Lo Rez Brewing— both of which are local and known for being delicious!

Weather Mark Tavern

Located: 1503 S Michigan Ave, Chicago, IL 60605

Located just a short walk away from both the Field Museum and Soldier Field, Weather Mark Tavern is 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 boasts one of the biggest rum selections in Chicago, rounding off at 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: There’s no better way to celebrate living lakeside than 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 offers American deli fare and refreshing beverages. While they are open for dinner as well, be sure to get there before 2 PM 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. Just 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!

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About the Author
Rebecca Denham

Rebecca is a freelance writer with eight years of journalism experience. She recently 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.