The Absolute Best Chicago-Style Pizza in San Diego: Top Picks

As a San Diego native with a deep love for pizza, I’ve scoured the city to uncover the finest Chicago-style pizzerias that bring the Windy City’s iconic deep-dish and stuffed pies to our sunny shores. These restaurants serve up hearty, cheesy masterpieces that satisfy both locals and tourists craving bold flavors and generous portions. From cozy, nostalgic spots to vibrant, modern joints, each pizzeria offers a unique experience, blending authentic Chicago recipes with San Diego’s laid-back charm.

Join me on this culinary journey as I share my top 10 picks, complete with rich details on flavors, ambiance, and service, ensuring you find the perfect slice to elevate your dining adventures in America’s Finest City.

Top 10 Best Chicago-Style Pizza Restaurants in San Diego

As a San Diego native with a passion for pizza, I’ve explored the city’s vibrant food scene to bring you the top 10 Chicago-style pizza spots that capture the essence of the Windy City’s iconic deep-dish and stuffed pies. Each restaurant offers a unique take on this hearty, cheesy delight, perfect for both locals and tourists craving an authentic taste of Chicago. Below, I share my personal experiences, diving into the flavors, ambiance, and service that make these pizzerias stand out in America’s Finest City.

Lefty’s Chicago Pizzeria

Basic Information
Address: 4030 Goldfinch St, San Diego, CA 92103
Phone: (619) 299-4030
Website: leftyspizza.com
Hours: Open from 11 AM to 8 PM daily

Highlights

Authentic Chicago-style deep-dish with a perfect crust
Signature Monster of the Midway pizza packed with bold flavors
Generous portions ideal for sharing
Chicago-inspired sides like Italian beef sandwiches
Friendly, welcoming service

What makes a pizza experience truly unforgettable? Stepping into Lefty’s Chicago Pizzeria, I was greeted by a cozy, nostalgic vibe adorned with Chicago Cubs and Bears memorabilia, instantly transporting me to the Windy City. This top-ranked spot in San Diego’s Chicago-style pizza toplist delivers an authentic experience that’s hard to beat.

The pizza here is nothing short of spectacular. The deep-dish Monster of the Midway, loaded with sausage, roasted garlic, and giardiniera, is a flavor-packed masterpiece, with a crust that’s crisp yet tender. For a vegetarian option, their spinach and mushroom deep-dish offers a harmonious blend of fresh veggies and gooey mozzarella, with hearty portions that ensure everyone leaves satisfied.

One standout side is the Italian beef sandwich, a Chicago classic. The juicy, slow-roasted beef, dipped in au jus and topped with spicy giardiniera, delivers a mouthwatering bite that perfectly complements the pizza. Each element, from the tender meat to the crusty bread, feels crafted with care, leaving me impressed with its authenticity.

The staff at Lefty’s is exceptionally warm and attentive, always ready to explain the menu or accommodate special requests. Their enthusiasm for Chicago-style cuisine elevates the dining experience, making every visit feel like a celebration of food and culture.

For anyone seeking an authentic Chicago-style pizza experience in San Diego, Lefty’s is a must-visit. With its unrivaled deep-dish, generous portions, and top-notch service, this pizzeria earns its place at the top of the Chicago-style pizza toplist. Whether you’re a local or a tourist, dive into this culinary gem for a meal that satisfies both heart and stomach.

Chicago Bros Pizzeria

Basic Information
Address: 10423 San Diego Mission Rd, San Diego, CA 92108
Phone: (619) 280-7703
Website: chicagobrospizzeriamenu.com
Hours: Open from 11 AM to 9 PM daily

Highlights

Rich, cheesy deep-dish pizzas with bold flavors
Signature stuffed pizza for an indulgent treat
Large portions perfect for groups
Tasty sides like jalapeno poppers
Welcoming, family-friendly service

Can a pizza joint feel like a warm hug from Chicago? Chicago Bros Pizzeria, nestled in a strip mall, exudes a lively, inviting atmosphere with its sports bar vibe and kid-friendly games. As the second gem on San Diego’s Chicago-style pizza toplist, it’s a local favorite for a reason.

The pizzas here are bold and satisfying. Their stuffed pizza, packed with pepperoni, sausage, and a thick layer of mozzarella, is a decadent work of art that oozes cheese with every bite. For a lighter yet equally delicious option, the pesto veggie deep-dish combines fresh basil and tomatoes for a vibrant, flavorful kick. The generous portions ensure you’ll have leftovers to savor.

Don’t miss their jalapeno poppers, a side that steals the show. These golden-fried beauties, stuffed with creamy cheese, offer a spicy, satisfying crunch that pairs perfectly with the rich pizzas. The fresh ingredients make every bite unforgettable.

The staff is incredibly friendly and efficient, always ready to guide you through the menu or ensure your order is perfect. Their genuine warmth makes dining here feel like a family gathering, enhancing every moment.

Chicago Bros Pizzeria is a top pick for anyone craving authentic Chicago-style pizza in San Diego. With its flavorful pies, hearty portions, and stellar service, it’s a standout on the Chicago-style pizza toplist. Locals and visitors alike should make a beeline for this delicious destination.

Regents Pizzeria

Basic Information
Address: 4150 Regents Park Row #100, La Jolla, CA 92037
Phone: (858) 550-0406
Website: regentspizza.com
Hours: Open from 11 AM to 9 PM daily

Highlights

Classic Chicago deep-dish with premium ingredients
Unique carne asada pizza for a local twist
Hearty portions great for sharing
Extensive craft beer selection to complement meals
Attentive, knowledgeable service

What’s the secret to a perfect pizza night? At Regents Pizzeria, I was welcomed by a vibrant, laid-back ambiance that blends San Diego’s casual vibe with Chicago’s bold flavors. Ranking high on the Chicago-style pizza toplist, this La Jolla gem is a must for pizza lovers.

The deep-dish pizzas here are impeccable, with a buttery crust that holds up beautifully. The classic sausage deep-dish is a savory delight, with fennel sausage and chunky tomato sauce creating a perfect balance. For something unique, the carne asada pizza, topped with salsa verde and pico de gallo, is a creative masterpiece with generous portions that satisfy.

Their mozzarella sticks are a standout side, crispy on the outside and oozing with melty cheese inside. Made with fresh, high-quality ingredients, they’re a delightful treat that elevates the meal.

The staff is engaging and attentive, offering beer pairing suggestions and ensuring every guest feels valued. Their passion for food shines through, making the experience memorable.

Regents Pizzeria is a top choice for Chicago-style pizza in San Diego, blending tradition with local flair. Its delectable pies, hearty portions, and exceptional service make it a standout on the Chicago-style pizza toplist. Whether you’re a local or visiting La Jolla, indulge here for an unforgettable meal.

Pizza 22

Basic Information
Address: 3001 Beech St, San Diego, CA 92102
Phone: (619) 381-4844
Website: pizza22sd.com
Hours: Open from 11 AM to 8 PM daily

Highlights

Authentic Chicago deep-dish with a thick, crispy crust
Signature meat lovers’ pizza for carnivore cravings
Generous portions ideal for groups
Freshly made garlic bread as a perfect side
Warm, community-focused service

Can a pizza joint feel like a hidden treasure? Pizza 22, tucked in South Park, offers a charming, cozy ambiance that feels like a warm embrace. As a standout on San Diego’s Chicago-style pizza toplist, it’s a haven for deep-dish enthusiasts.

The deep-dish pizzas are phenomenal, with a crust that’s crisp yet chewy. The meat lovers’ pizza, piled high with sausage, pepperoni, and ham, is a carnivore’s dream, bursting with bold flavors. The veggie deep-dish, with its fresh spinach and mushrooms, offers a vibrant, satisfying alternative. Hearty portions ensure everyone leaves full.

The garlic bread, made fresh daily, is a buttery, aromatic delight. Toasted to golden perfection, it’s the ideal companion to the rich pizzas, leaving me speechless with every bite.

The staff is genuinely kind and attentive, creating a community-like atmosphere that makes every visit special. Their dedication ensures a seamless dining experience.

Pizza 22 is a must-visit for authentic Chicago-style pizza in San Diego. With its flavorful pies, generous portions, and heartfelt service, it shines on the Chicago-style pizza toplist. Locals and tourists should savor this gem for a true taste of Chicago.

Chicago Pizza Company

Basic Information
Address: 10423 San Diego Mission Rd, San Diego, CA 92108
Phone: (619) 280-7703
Website: Not available
Hours: Open from 11 AM to 8 PM daily

Highlights

Traditional Chicago deep-dish with robust flavors
Customizable pizzas for personalized creations
Large portions perfect for takeout
Tasty fried mushrooms as a unique side
Friendly, efficient service

What’s the joy of finding a pizza spot off the beaten path? Chicago Pizza Company in Santee offers a welcoming, no-frills vibe that feels like a hidden gem. This spot ranks high on San Diego’s Chicago-style pizza toplist for its authentic flavors.

The deep-dish pizzas are outstanding, with a thick crust that’s perfectly baked. The classic pepperoni deep-dish is a savory triumph, with spicy pepperoni and rich sauce. The custom veggie pizza, with fresh onions and peppers, is a colorful, flavorful option. Generous portions make it ideal for sharing.

Their fried mushrooms are a crispy, golden treat, lightly battered and served with ranch. The fresh, earthy flavors make them a standout side that complements the hearty pizzas.

The staff is approachable and quick, ensuring orders are accurate and timely, especially for takeout. Their genuine care enhances the experience.

For Chicago-style pizza lovers in San Diego, Chicago Pizza Company is a top contender. Its delicious pies, hearty portions, and reliable service make it a star on the Chicago-style pizza toplist. Locals and visitors should head to Santee for a satisfying meal.

Rosati’s Pizza

Basic Information
Address: 5855 Mission Gorge Rd, San Diego, CA 92120
Phone: (619) 280-7703
Website: myrosatis.com
Hours: Open from 11 AM to 9 PM daily

Highlights

Classic Chicago deep-dish with rich flavors
Signature sausage pizza for meat lovers
Generous portions great for groups
Mozzarella sticks as a crowd-pleasing side
Attentive, sports-pub vibe service

What makes a pizza spot feel like a game-day hangout? Rosati’s Pizza, with its lively, sports-pub atmosphere, is a standout on San Diego’s Chicago-style pizza toplist, offering a taste of Chicago with a local twist.

The deep-dish pizzas are flawless, with a buttery crust and robust sauce. The signature sausage pizza is a meaty masterpiece, with fennel sausage and gooey cheese. The veggie deep-dish, packed with fresh peppers and olives, is vibrant and satisfying. Hearty portions ensure no one leaves hungry.

Their mozzarella sticks are a crispy, cheesy delight, fried to golden perfection and served with marinara. The fresh ingredients make them a must-try side.

The staff is energetic and attentive, creating a fun, welcoming vibe that’s perfect for groups. Their quick service keeps the experience seamless.

Rosati’s is a top choice for Chicago-style pizza in San Diego. With its delicious pies, generous portions, and lively service, it’s a highlight on the Chicago-style pizza toplist. Locals and tourists should visit for a memorable meal.

Caps Pizza & Bar

Basic Information
Address: 4046 30th St, San Diego, CA 92104
Phone: (619) 282-3000
Website: Not available
Hours: Open from 11 AM to 9 PM daily

Highlights

Flavorful Chicago deep-dish with fresh ingredients
Artichoke heart pizza for a unique twist
Large portions ideal for sharing
Garlic bread as a perfect side
Friendly, hip atmosphere

What’s the allure of a pizza spot with Chicano flair? Caps Pizza & Bar in North Park offers a vibrant, hip ambiance with Chicano art and music, making it a unique entry on San Diego’s Chicago-style pizza toplist.

The deep-dish pizzas are exceptional, with a crust that’s crisp yet chewy. The artichoke heart pizza is a creative gem, blending creamy artichokes with tangy sauce. The classic pepperoni deep-dish delivers bold, savory flavors. Generous portions make it perfect for groups.

Their garlic bread is a buttery, aromatic standout, baked to golden perfection with fresh herbs. It’s a delightful complement to the rich pizzas.

The staff is warm and engaging, creating a lively, inclusive vibe. Their attention to detail ensures a great experience.

Caps Pizza & Bar is a top pick for Chicago-style pizza in San Diego. Its unique pies, hearty portions, and vibrant service make it a star on the Chicago-style pizza toplist. Visit for a flavorful adventure.

Hoboken Pizza & Beer Joint

Basic Information
Address: 1459 Garnet Ave, San Diego, CA 92109
Phone: (858) 270-7766
Website: Not available
Hours: Open from 11 AM to 10 PM daily

Highlights

Authentic Chicago deep-dish with balanced flavors
Signature meat lovers’ pizza for hearty appetites
Generous portions great for beachside meals
Crispy onion rings as a standout side
Welcoming, laid-back service

What’s the vibe of a beachside pizza haven? Hoboken Pizza & Beer Joint in Pacific Beach offers a relaxed, inviting atmosphere, perfect for a post-beach meal. It’s a gem on San Diego’s Chicago-style pizza toplist.

The deep-dish pizzas are perfectly executed, with a crisp, flavorful crust. The meat lovers’ pizza, loaded with sausage and pepperoni, is a hearty delight. The veggie deep-dish, with fresh tomatoes and spinach, is vibrant and satisfying. Large portions ensure everyone’s happy.

Their onion rings are a crispy, golden treat, fried to perfection with a sweet, tangy flavor. They’re a must-order side that elevates the meal.

The staff is friendly and relaxed, creating a beachside vibe that feels effortless. Their quick service keeps the experience smooth.

Hoboken is a top choice for Chicago-style pizza in San Diego. Its delicious pies, generous portions, and laid-back service make it a standout on the Chicago-style pizza toplist. Stop by for a beachside feast.

Sicilian Thing Pizza

Basic Information
Address: 3001 Beech St, San Diego, CA 92102
Phone: (619) 381-4844
Website: Not available
Hours: Open from 11 AM to 8 PM daily

Highlights

Chicago-inspired deep-dish with a Sicilian twist
Signature Almost Lasagna pizza for a unique experience
Hearty portions perfect for groups
Freshly baked breadsticks as a tasty side
Warm, attentive service

What’s the charm of a pizza spot with Sicilian flair? Sicilian Thing Pizza in South Park offers a cozy, welcoming ambiance that blends Chicago and Sicilian styles, earning its spot on San Diego’s Chicago-style pizza toplist.

The deep-dish pizzas are outstanding, with a thick, crispy crust. The Almost Lasagna pizza, layered with meatballs and ricotta, is a creative masterpiece. The veggie deep-dish, with fresh zucchini and peppers, is vibrant and flavorful. Generous portions ensure satisfaction.

Their breadsticks, baked fresh, are a buttery, soft delight, perfect for dipping in marinara. The fresh ingredients make them a standout side.

The staff is kind and attentive, creating a homey vibe that feels personal. Their careful service enhances every visit.

Sicilian Thing Pizza is a top pick for Chicago-style pizza in San Diego. Its unique pies, hearty portions, and warm service make it a gem on the Chicago-style pizza toplist. Visit for a memorable meal.

Buona Forchetta - South Park

Basic Information
Address: 3001 Beech St, San Diego, CA 92102
Phone: (619) 381-4844
Website: Not available
Hours: Open from 12 PM to 9 PM daily

Highlights

Chicago-style deep-dish with an Italian twist
Signature margherita deep-dish for classic lovers
Large portions ideal for sharing
Freshly made tiramisu as a sweet side
Charming, attentive service

What’s the magic of a pizza spot with Italian charm? Buona Forchetta - South Park offers a cozy, elegant ambiance that feels like a slice of Italy. It’s a standout on San Diego’s Chicago-style pizza toplist for its unique approach.

The deep-dish pizzas are impeccable, with a crisp, chewy crust. The margherita deep-dish, with fresh basil and mozzarella, is a classic masterpiece. The sausage and pepper deep-dish delivers bold, savory flavors. Hearty portions ensure everyone’s satisfied.

Their tiramisu is a creamy, decadent treat, layered with espresso-soaked cake and mascarpone. It’s a perfectly crafted dessert that leaves you speechless.

The staff is gracious and attentive, creating a warm, inviting experience. Their passion for food shines through, making every visit special.

Buona Forchetta is a top choice for Chicago-style pizza in San Diego. Its flavorful pies, generous portions, and charming service make it a highlight on the Chicago-style pizza toplist. Indulge here for an unforgettable meal.

Conclusion: Your Guide to Chicago-Style Pizza Bliss

My journey through San Diego’s Chicago-style pizza scene reveals a vibrant mix of pizzerias, each delivering authentic, flavor-packed pies with crispy crusts, gooey cheese, and creative toppings. From Lefty’s nostalgic charm to Buona Forchetta’s Italian flair, these spots offer unforgettable meals for pizza lovers. Whether you’re a local or a visitor, this toplist guides you to the best Chicago-style pizza experiences, complete with hearty portions and warm service. Explore these gems with San Diego Nav and savor the bold, comforting taste of Chicago right here in our coastal paradise.