Summer House Santa Monica is one of The 15 Best Places for Calamari in Chicago.

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 LordChicago Food Lord: Their Fresh Burrata and Spicy Calamari are amazing, I highly recommend it

Andre W.Andre Williams: Great ambience and great food...calamari and carmelized brussels sprouts are awesome

David K.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).

Club Lucky is one of The 15 Best Places for Calamari in Chicago.

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 LuckyClub Lucky: We are famous in Chicago for our fresh fried and grilled calamari! Just ask someone. Read more.

Tracy M.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 S.Karen Slack: Get the Calamari! The bacon wrapped figs and meatballs were filled with awesomeness.

Calo Ristorante is one of The 15 Best Places for Calamari in Chicago.

3. Calo Ristorante

8.8
5343 N Clark St (at Summerdale Ave), Chicago, IL
Italian Restaurant · Andersonville · 72 tips and reviews

Lori B.Lori B: Great Penne Vodka!!! So tasty and large portion, enough to share! Calamari is tender and lightly fried! Service was phenomenal!

Joey D.Joey D: Got to have the grilled calamari!! It's a fav alright!!

Christopher S.Christopher Sterling: Get calamari fritti Davola if you like it spicy!!

Quartino is one of The 15 Best Places for Calamari in Chicago.

4. Quartino

8.8
626 N State St (at W Ontario St), Chicago, IL
Italian Restaurant · Near North Side · 345 tips and reviews

Steve S.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 S.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.Katie B.: Try the crispy calamari and the Quattro Formaggio pizza!

Fish Bar is one of The 15 Best Places for Calamari in Chicago.

5. Fish Bar

8.6
2956 N Sheffield Ave (at W Wellington Ave), Chicago, IL
Seafood Restaurant · Lakeview · 103 tips and reviews

Josh G.Josh Gilbert: Calamari "Federal Hill" style is a must.

Danielle @.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 EatsSerious 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

Tufano's Vernon Park Tap is one of The 15 Best Places for Calamari in Chicago.

6. Tufano's Vernon Park Tap

8.3
1073 W Vernon Park Pl (at Racine), Chicago, IL
Italian Restaurant · University Village - Little Italy · 44 tips and reviews

Kat M.Kat Man Do: Best Calamari in little Italy!!!

Kat M.Kat Man Do: Best Calamari in Chitown!!!

Ethan S.Ethan Smith: Calamari was decent with the sauce. Chicken parm was very good. Staff is very nice except for the man in the front 6.5/10

Topo Gigio Ristorante is one of The 15 Best Places for Calamari in Chicago.

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 D.Raphael De Mello: Fish, calamari are great options! The gnocchi is good, and you can also change it to bolognese sauce. Enjoy!

Renee D.Renee Dreznes: The grilled calamari is the best I've ever had. Highly recommended!

Jodi E.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.

Cafe Bionda is one of The 15 Best Places for Calamari in Chicago.

8. Cafe Bionda

7.9
1924 S State St, Chicago, IL
Italian Restaurant · South Loop · 30 tips and reviews

Joshua "LEGO" l.Joshua "LEGO" lohrman: Try the veal parmesan and the calamari

Chanda D.Chanda Dunmars: The grilled calamari should definitely be on the try list

James F.James Faretta: The grilled calamari is listed as an appetizer but there's enough deliciousness there to enjoy as an entree!

Mia Francesca is one of The 15 Best Places for Calamari in Chicago.

9. Mia Francesca

8.8
3311 N Clark St (at W Aldine Ave.), Chicago, IL
Italian Restaurant · Lakeview · 53 tips and reviews

Bobby M.Bobby Moss: Great Calamari!!!

Joshua N.Joshua Nard: Excellent. Great staff. Calamari and Risotto was fantastic. Salmone was well prepared. Bread Pudding was perfect.

StephanieStephanie: The salmon is delicious! Along with the calamari and really everything else.

Harry Caray's Italian Steakhouse is one of The 15 Best Places for Calamari in Chicago.

10. Harry Caray's Italian Steakhouse

8.2
33 W Kinzie St (at Dearborn St), Chicago, IL
Steakhouse · Near North Side · 107 tips and reviews

Cristina M.Cristina Marrero: By checking in u receive a complementary tiramisu, i went with 5 ppl and we were all able to share, it was huuge and by far the best tiramisu any of us had ever had! The calamari was also delicious!

Winona Y.Winona Y: the best Calamari ..;).

Bailey S.Bailey Shemenski: Calamari and house made cocktail sauce

Roots Handmade Pizza is one of The 15 Best Places for Calamari in Chicago.

11. Roots Handmade Pizza

8.1
1924 W Chicago Ave (at N Winchester Ave), Chicago, IL
Pizzeria · East Ukrainian Village · 103 tips and reviews

Xandrea R.Xandrea Rapier: Grilled shrimp& calamari is delicious if your looking for a healthy option.

Carly B.Carly B.: Open storefront, great craft beer selection and really good calamari!

Heather D.Heather D: We just stopped for appetizers and beer but the calamari and monkey bread were perfect.

Fireside Restaurant & Lounge is one of The 15 Best Places for Calamari in Chicago.

12. Fireside Restaurant & Lounge

8.0
5739 N Ravenswood Ave (at W Rosehill Dr), Chicago, IL
Bar · Edgewater · 53 tips and reviews

Marc E.Marc Emmanuel: The best Calamari I'm town!

Janie C.Janie Costanzo: Calamari to die for!!!!

Alejandro G.Alejandro Garcia: The calamari is so good here! You can't go wrong with their thin crust pizza, fish and chips are delicious.

Orso's Restaurant is one of The 15 Best Places for Calamari in Chicago.

13. Orso's Restaurant

7.7
1401 N Wells St (at W Schiller St), Chicago, IL
Italian Restaurant · Old Town · 75 tips and reviews

LucretiaLucretia: Beautiful backyard patio, good grilled calamari, but really bad, oily, poorly-seasoned Caesar salad. Pastas were good!

Antonio M.Antonio Milito: Best calamari in Chicago !!

Chad C.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.

Sapori Trattoria is one of The 15 Best Places for Calamari in Chicago.

14. Sapori Trattoria

8.5
2701 N Halsted St (at Schubert Ave), Chicago, IL
Italian Restaurant · Park West · 89 tips and reviews

FlemingFleming: Grilled calamari app = boss.

Anastasia B.Anastasia Belozertseva: I want to put in a word for grilled calamari - simply outstanding in a yummy balsamic reduction sauce

Melissa E.Melissa E: The grilled calamari is my favorite. Then for a main you can't go wrong with any pasta dish. Personally love the gnocchi. Also a wonderful accommodating staff.

Francesca's on Chestnut is one of The 15 Best Places for Calamari in Chicago.

15. Francesca's on Chestnut

8.5
200 E Chestnut St, Chicago, IL
Italian Restaurant · Streeterville · 23 tips and reviews

Jeff F.Jeff Fisher: Doc at the bar may be Chicago's best bartender!! All food is great! Luv the calamari & beef carpaccio to start.

Stephen L.Stephen Lawrence: Get the fried calamari, frutti de mare and of course the tiramisu!!!!

O. K.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.