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Illinois' best

Upscale calamari

Calamari served in an upscale setting that feels refined rather than just overpriced.

Based on 628 Opinions
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Updated April 2026
01
A+ Italian Steakhouse image 1
A+ Italian Steakhouse image 2
A+ Italian Steakhouse image 3
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Old-school Italian steakhouse with classic chandeliers and a spacious dining area creates a cozy, romantic vibe. Valet parking adds convenience while a small bar offers superb cocktails and retro music. Atmosphere stays inviting and comfortable with a touch of elegance throughout.

Grilled calamari stands out with a unique and flavorful taste. It ranks among the top-tier appetizers, alongside baked clams and octopus.

Warm, inviting ambiance with soft lighting and elegant dรฉcor creates a cozy, intimate setting. The atmosphere suits a relaxed evening, whether for a date night or dinner with friends.

People are saying

"The food here is cooked perfectly and packed with flavor."

"I highly recommend the grilled calamari; it's amazing."

"The upscale Italian food here is fresh, flavorful, and perfectly cooked."

Good to know

1

Happy hour offers half-price appetizers on Thursday evenings.

2

Reservations are recommended for dinner service, especially on weekends.

3

Expect a wait time of 30-45 minutes during peak dinner hours.

02
Raki Restaurant image 1
Restaurant

Modern, cozy space with chandeliers and tasteful decor creates a luxurious, relaxing atmosphere. Live music on Friday nights adds to the warm, welcoming vibe. The setting supports good conversation and feels distinct from typical suburban restaurants.

Calamari comes out light and crispy, never rubbery. It tastes insanely fresh and cooks perfectly every time.

Elegant yet warm atmosphere combines with authentic Greek cuisine to create a refined dining experience. The setting feels comfortable while maintaining a sense of sophistication throughout.

People are saying

"The food here is so authentic and fresh, it reminds me of Greece."

"The food here is phenomenal, flavorful, and perfectly prepared."

"The calamari is so fresh and perfectly cooked."

Good to know

1

Reservations are recommended for special events like Valentine's Day.

2

The restaurant features live Balkan music on select nights.

3

Gluten-free options are available, with dedicated fryers to prevent cross-contamination.

03
Eddie V's Prime Seafood image 1
Seafood restaurant

Seafood restaurant offers a quiet, sophisticated atmosphere with live jazz music enhancing the mood. Guests often enjoy private rooms and complimentary valet parking. The setting features elegant interiors highlighted by a central chandelier and fine dining touches.

Calamari comes as a standout appetizer with an Asian twist. It pairs well with other seafood starters like lobster bisque and Maine lobster tacos.

Quiet atmosphere and elegant ambiance create a sophisticated vibe throughout the restaurant.

People are saying

"The steak here is great, and the servers are knowledgeable."

"The calamari here is amazing, with attentive and friendly service."

"The upscale service here is impeccable and attentive to detail."

Good to know

1

Happy hour features discounted seafood and steak selections from 4-6pm on weekdays.

2

Live jazz music is performed on Thanksgiving and select weekends.

3

Reservations are recommended for special occasions to ensure table decorations.

04
MIKAMI IZAKAYA & RAMEN image 1
Japanese restaurant

Japanese restaurant combines industrial-chic design with elegant touches for an upscale look and vibrant, casual vibe. Atmosphere stays quiet and spacious, fitting for romantic dates or relaxed chats. Full bar offers Japanese beer on tap and notable cocktails alongside rare ramen varieties.

Grilled calamari comes out perfectly cooked with a flavorful dipping sauce. Whole calamari shows great flavor and pairs well with other grilled items like chicken skewers and shisito peppers.

Industrial-chic design blends with elegant touches to create a beautiful, airy space. The atmosphere feels clean and high-end with a simple yet refined style.

People are saying

"The Japanese food, especially the ramen, is flavorful and comforting."

"The space here is beautiful and elegant."

"The calamari here is cooked perfectly with great flavor."

Good to know

1

Lunch specials are available for $21.95, including a side, main dish, and drink.

2

Happy hour features discounted cocktails and appetizers, making it a great time to visit.

3

The restaurant offers a variety of Japanese dishes beyond ramen, like gyudon.

05
Blue Fire Restaurant image 1

Restaurant offers a cozy European atmosphere with beautiful decor featuring blue windows and dark walls. Live jazz music plays on heated outdoor patios with fire pits, creating a relaxing vibe. Guests enjoy a mix of indoor elegance and charming outdoor seating.

Crispy fried calamari comes in a good size portion and tastes very tasty. Squid ink pasta includes tender calamari and shrimp.

Atmosphere feels elegant and warm, with a vibe that recalls being abroad. Evening styles add a gorgeous touch to the setting.

People are saying

"The cocktails here are creative, balanced, and perfectly mixed."

"It's the perfect cozy spot for a romantic date night."

"The Upscale food is incredible, with every dish full of flavor."

Good to know

1

Happy hour runs daily from 3-6 PM with half-price drinks.

2

Live jazz music is featured on Saturdays from 6-9 PM.

3

Karaoke starts after 9 PM, creating a lively atmosphere.

06
Ascione Bistro Skokie image 1
Italian restaurant

Italian restaurant offers modern art deco design with velvet booths, leather chairs, and gold details creating an upscale yet cozy atmosphere. Large bar and lounge with fireplace provide spaces for both casual and special occasions. Outdoor seating and free valet parking add convenience to the elegant dining experience.

Lightly crisp outside and tender inside, the calamari comes with a bit of spice. Grilled options deliver an absolutely phenomenal texture and flavor.

The setting features a chic and sophisticated ambiance with warm lighting and tasteful dรฉcor. It balances elegance with a cozy, inviting vibe suitable for both casual and special occasions.

People are saying

"The service here is outstanding and attentive."

"The food here is delicious, fresh, and flavorful."

"The calamari is tender with amazing flavor."

Good to know

1

Happy hour deals are available only at the bar or high tops.

2

Reservations are recommended as the restaurant is likely to get busy.

3

Valet parking is available for guests.

07
Somerset image 1
New American restaurant

Gold and blue decor blends vintage and modern styles in an upscale yet approachable setting. Seating options include comfortable round booths and a beautiful outdoor terrace with lively people watching. The atmosphere stays elegant and cozy with occasional live piano music enhancing the vibey ambiance.

Crispy and flavorful calamari melts in your mouth with a white sauce that complements it beautifully. The texture stays tender, not chewy, making it a standout appetizer option.

Elegant atmosphere with dimly lit tables, gold candles, and beautiful chandeliers creates a cozy yet stylish setting.

People are saying

"The patio is a really nice spot for people watching."

"The calamari here is crispy, flavorful, and melts in your mouth."

"It's so elegant and cozy inside."

Good to know

1

Valet parking is available, making it easier to find a spot.

2

Happy hour features a frequently changing menu with discounted drinks.

3

Expect a $24 charge for the burger and $18 for avocado toast.

08
TNT Rooftop Restaurant image 1

Rooftop setting offers beautiful views and a relaxing atmosphere with top-tier music from DJs playing 90s and 2000s hits. The vibe suits date nights and small parties, featuring a semi-private room. Food and drinks include flavorful seafood and cocktails, with standout items like lamb chops and lemon drop cocktails.

Crunchy texture stands out with a flavorful kick. Comes with a deliciously spicy sauce and cocktail sauce on the side.

Ambience feels elegant and sophisticated with a modern touch. The atmosphere stays consistently classy and professional.

People are saying

"I thought the food here was amazing."

"The vibe here is so elegant and sophisticated."

"The calamari here is flavorful and crunchy."

Good to know

1

Happy hour runs all night on Thursdays for ladies with special pricing.

2

Wine Wednesday offers three tastings and a full glass for $20.

3

An 18% gratuity is added for all parties, regardless of size.

09
Follia image 1
Restaurant

Authentic Italian restaurant with modern yet timeless decor and a balanced indoor-outdoor seating arrangement creates an elegant yet welcoming atmosphere. Soft lighting and spacious table settings contribute to a cozy, sophisticated vibe that blends European style with comfort.

Calamari comes with imported baby Italian artichokes that stand out. The dish is perfectly cooked and served with thoughtful plating.

Elegant atmosphere sets a sophisticated tone with beautiful decor. The vibe feels welcoming yet upscale.

People are saying

"The food here is amazing and creative."

"It's an elegant and sophisticated spot with a warm atmosphere."

"The calamari here is so elegant and beautifully presented."

Good to know

1

The restaurant has a strict dress code; no shorts for men, regardless of style.

2

A $75 corkage fee applies if you bring your own wine.

3

Expect a 20% service charge added to your bill for dining.

10
Olivia's Italian Restaurant image 1
Italian restaurant

Italian restaurant offers a lively and inviting atmosphere with outdoor patio seating and a cozy, warm interior despite its large size. Large televisions above the bar create a bar-and-grill vibe rather than a refined dining experience. The private room provides a spacious and private setting for groups.

Fried calamari arrives fresh and cooked to perfection. It stands out as a scrumptious starter often favored alongside other dishes.

Cozy and elegant dining atmosphere creates a romantic, classy vibe similar to upscale spots in downtown Chicago or New York City.

People are saying

"The food here is amazing, they'll make anything you want."

"The staff here is so welcoming and personable, making it feel upscale."

"The calamari here is so fresh and perfectly fried."

Good to know

1

The restaurant offers gluten-free options on the menu.

2

Expect no wait time for large groups during peak hours.

3

Prices are reasonable for the quality of food served.

11
Positano Ristorante - Wheaton image 1

Spacious restaurant features dimly lit, sleek design with classic Italian music and a stacked, see-through wine cellar. Separate bar, lounge, and outdoor patio create distinct seating areas. Atmosphere suits celebrations and family dinners but can become loud and lively as the evening progresses.

Fritti misto features mostly tender calamari with a few shrimp and scallops. Calamari appears as a soft appetizer alongside other dishes like bruschetta and vodka pasta.

Sophisticated Italian atmosphere offers three seating options: restaurant, bar, and outdoor area. Moody lighting and classic Italian music create a romantic, elegant, and classy vibe without feeling too formal.

People are saying

"The food here is amazing, truly outstanding."

"The service here makes it a great spot for a date."

"The calamari here is so tender, it's amazing."

Good to know

1

Parking is easily accessible near the restaurant.

2

The menu offers a wide selection of Italian dishes.

3

Expect a large group fee if dining with more than a few people.

12
Florio's Italian image 1
Food and drink

Elegant Italian restaurant with 40โ€™s-inspired decor and marble floors featuring Italian landscapes. Atmosphere feels warm and inviting, blending cozy family vibes with refined city elegance. Seating offers comfortable privacy, making it suitable for special occasions.

Grilled calamari arrives perfectly cooked and tender. It works well as a bar appetizer to start the meal.

Elegant design and a relaxed Italian vibe create a sophisticated and classy atmosphere. The setting feels both elegant and calming.

People are saying

"The Italian dinner spots here are amazing, truly real Italian food."

"Our waiter Joshua was a gentleman, charming and attentive."

"The calamari here is cooked perfectly."

Good to know

1

Reservations can be made online and are recommended for busy nights.

2

Expect a wait time of 30 minutes during peak dinner hours.

3

Parking is available on-site, but it can fill up quickly during weekends.

13
Unico Restaurante image 1
Italian restaurant

Elegant space with black walls and a warm dining room creates an intimate yet lively atmosphere. The vibe blends old Chicago style with a chill, welcoming energy suitable for dates or group outings. Music adds to the ambiance, enhancing the stylish and accommodating setting.

Fried calamari comes out light and crispy, paired with a sweet chili sauce that adds a nice balance. The sauce blends spicy and sweet flavors but the dish is solid, not exceptional.

Elegant design and a very accommodating atmosphere define the space. Interiors are beautiful, clean, and consistently elegant.

People are saying

"The Italian food here is artfully plated and delicious."

"The Upscale food is delicious, from appetizers to desserts."

"The fried calamari is light and crispy."

Good to know

1

Unico Restaurante is currently BYOB, allowing guests to bring their own beverages.

2

There is a $25 corkage fee per bottle for those bringing their own wine.

3

Street parking is easy, and valet service is available for convenience.

14
Southern Chicago image 1

Elegant space features beautiful dรฉcor and a warm, comfortable atmosphere with great music enhancing the vibe. Guests enjoy thoughtfully crafted cocktails and high-quality Southern-inspired dishes in a setting that feels both inviting and refined.

Elegant design creates a sophisticated ambiance with a grown and sexy vibe. The space feels like an epicurean paradise crafted for upscale dining.

People are saying

"The food here is amazing, fresh, and thoughtfully prepared."

"It's an elegant place with a gorgeous, sophisticated vibe."

"You have to try the fried calamari here."

Good to know

1

Happy hour offers great prices on food and drinks.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available for guests.

15
Mastro's Steakhouse image 1
Fine dining restaurant

Elegant dining space features dim, cozy lighting and live music performances that create a romantic, upscale atmosphere. The lounge offers an upbeat vibe with talented singers and pianists providing background entertainment. Seating is close together, enhancing a lively, intimate feel.

Fried calamari stands out as a delicious appetizer and a favorite way to start dinner here.

Warm and elegant atmosphere sets the tone here. Live music adds to the upscale and refined vibe.

People are saying

"The steak here is amazing, with attentive and friendly staff."

"The atmosphere here is upscale, elegant, and visually appealing."

"The calamari here was delicious and a favorite appetizer."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted appetizers.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available and recommended for convenience.

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