Best Calamari in Uptown, Chicago
The 8 top-rated calamari in Uptown, Chicago, ranked by flavor score.
The top choice is fried calamari at Tiffany's On Broadway (4645 N Broadway St), with a flavor score of 86 out of 100 from 5 diner ratings. Flavor scores come from what real diners say in their reviews. Last updated August 27, 2026. How flavor scores work →
Best Calamari across Chicago→- Ranked #1At Tiffany's On Broadway4645 N Broadway St
- Ranked #2At Tiffany's On Broadway4645 N Broadway St
Lightly breaded calamari cooked to perfection pairs well with flavorful dipping sauces like cocktail and garlic aioli.
- Ranked #3At Silver Seafood Restaurant4829 N Broadway St
- Ranked #4At Bar Roma5101 N Clark St Ste 1
- Ranked #5At The Reservoir844 W Montrose Ave
Calamari is praised for being lightly fried and flavorful, but some found it overcooked and chewy with small portions.
- Ranked #6At Pick Me Up Cafe4882 N Clark St
- Ranked #7At Fin Sushi Bar1742 W Wilson Ave
- Ranked #8At Clark El Ranchito4651 N Clark St
The calamari was consistently criticized for being rubbery, overcooked, and served with unsuitable dipping sauces, making it inedible.