Best Old Fashioneds in Near South Side, Chicago
The 8 top-rated old fashioneds in Near South Side, Chicago, ranked by flavor score.
The top choice is old fashioned at The Chicago Firehouse Restaurant (1401 S Michigan Ave), with a flavor score of 86 out of 100 from 17 diner ratings. Flavor scores come from what real diners say in their reviews. Last updated August 27, 2026. How flavor scores work →
Best Old Fashioneds across Chicago→- Ranked #1At The Chicago Firehouse Restaurant1401 S Michigan Ave
The Old Fashioned impresses with its smooth bourbon flavor and balanced sweetness, making it a favorite among patrons.
- Ranked #2At MIKAMI IZAKAYA & RAMEN1400 S Michigan Ave
- Ranked #3At Buttercup75 E 16th St
- Ranked #4At Southern Chicago2000 S Wabash Ave
The old fashioned has received praise for its flavor and quality, though some found it average or inconsistent in preparation.
- Ranked #5At Oliver’s1639 S Wabash Ave
- Ranked #6At Fatpour McCormick: Ultimate Chicago Sports Bar2206 S Indiana Ave
- Ranked #7At VU Rooftop133 E Cermak Rd
The Old Fashioned often disappoints with issues like being watered down, poorly mixed, or lacking in flavor.
- Ranked #8At Chicago Oyster House1933 S Indiana Ave