1. Summer House Santa Monica
8.7
1954 N Halsted St (btwn Armitage Ave & Willow St), Chicago, IL
American Restaurant · North Side · 134 tips and reviews
Chicago Food Lord: Their Fresh Burrata and Spicy Calamari are amazing, I highly recommend it
Andre Williams: Great ambience and great food...calamari and carmelized brussels sprouts are awesome
David K.: Great atmosphere, service and menu. Calamari was fantastic and so was the French dip (make sure to splurge and get it with bacon and cheddar).
2. Club Lucky
9.0
1824 W Wabansia Ave (at N Honore St), Bucktown/Wicker Park, IL
Italian Restaurant · Bucktown · 62 tips and reviews
Club Lucky: We are famous in Chicago for our fresh fried and grilled calamari! Just ask someone. Read more.
Tracy Martorello: Pretty sure you can't go wrong with anything on the menu. Try the calamari calabrese grilled, mission fig salad, eggplant parm, and martini night on Tuesday.
Karen Slack: Get the Calamari! The bacon wrapped figs and meatballs were filled with awesomeness.
4. Quartino
8.8
626 N State St (at W Ontario St), Chicago, IL
Italian Restaurant · Near North Side · 345 tips and reviews
Steve Sielatycki: Rob, this is our favorite place by our old apt. Try the salumeria tasting with the eggplant salad, duck prosciutto and taleggio for sure. Calamari also basic and excellent.
Rosalina So: The organization and execution of food service are top notch. The menu literally is awesome from the calamari to the pizza to the bordetto to the tiramisu are excellent... And the prices arent bad!
Katie B.: Try the crispy calamari and the Quattro Formaggio pizza!
5. Fish Bar
8.6
2956 N Sheffield Ave (at W Wellington Ave), Chicago, IL
Seafood Restaurant · Lakeview · 103 tips and reviews
Josh Gilbert: Calamari "Federal Hill" style is a must.
Danielle @DanielleDuncan: i love the fried calamari, garlic bread, shrimp po' boy, rock shrimp (wet), they had scallops as a special (AMAZING!)- ask for beer pairing too! My fav cocktail is #3!
Serious Eats: The Calamari here are exemplary--breaded, deep fried, and tossed with picked banana pepper, jalapeño, and sliced garlic, a light grating of Parmesan cheese
7. Topo Gigio Ristorante
8.6
1516 N Wells St (btwn North Ave & Schiller St), Chicago, IL
Italian Restaurant · Old Town · 79 tips and reviews
Raphael De Mello: Fish, calamari are great options! The gnocchi is good, and you can also change it to bolognese sauce. Enjoy!
Renee Dreznes: The grilled calamari is the best I've ever had. Highly recommended!
Jodi E.: The Insalata Ai Frutti Di Mare is AMAZING! Fresh steamed calamari and shrimp (I did not include the mussels or clams) over salad with citrus vinaigrette.
13. Orso's Restaurant
7.7
1401 N Wells St (at W Schiller St), Chicago, IL
Italian Restaurant · Old Town · 75 tips and reviews
Lucretia: Beautiful backyard patio, good grilled calamari, but really bad, oily, poorly-seasoned Caesar salad. Pastas were good!
Antonio Milito: Best calamari in Chicago !!
Chad Curry: What a gem. The weekend piano is really nice for the ambiance. It's not your typical Old Town stop. Traditional Italian. Calamari alla griglia was nice and tender as were the sausage and peppers.
Jeff Fisher: Doc at the bar may be Chicago's best bartender!! All food is great! Luv the calamari & beef carpaccio to start.
Stephen Lawrence: Get the fried calamari, frutti de mare and of course the tiramisu!!!!
O. K.: The beef Carpaccio and the pastas are always a delight, and everything else is absolutely delicious. This is one of my favorite restaurants in Chicago.