Best Pizza Deliveries
in Chesapeake

We analyzed hundreds of pizzerias to find the best delivery options in Chesapeake. Our ranking is based on core quality, reliability, and real customer feedback.

✓ Verified Updated May 2026 · 5 restaurants ranked

Quick Overview

# Business Name Badge Rating Score
1 Andiamo Ristorante & Pizza Napoletana
500 S Battlefield Blvd, Chesapeake, VA 23322, USA
Pricey Portions
★ ★ ★ ★ ☆
4.6
84.36
2 Andy Boys Pizza
3916 Portsmouth Blvd A4, Chesapeake, VA 23321, USA
Neighborhood Slice
★ ★ ★ ★ ☆
4.6
83.47
3 Windy city pizza chesapeake
480 Kempsville Rd, Chesapeake, VA 23320, USA
Chicago Style
★ ★ ★ ★ ☆
4.3
82.17
4 Frank's Pizza
2544 Bainbridge Blvd B, Chesapeake, VA 23324, USA
Pepperoni Dip
★ ★ ★ ★ ☆
4.4
80.71
5 Yianni's Neighborhood Pizzeria and Family Restaurant
940 Cedar Rd #106, Chesapeake, VA 23322, USA
Neighborhood Staple
★ ★ ★ ★ ☆
4.6
80.10

Detailed Reviews

Andiamo Ristorante & Pizza Napoletana
Pricey Portions
1
Andiamo Ristorante & Pizza Napoletana
84.36
Score
500 S Battlefield Blvd, Chesapeake, VA 23322, USA

Andiamo Ristorante & Pizza Napoletana operates from its Chesapeake location at 500 S Battlefield Blvd. The establishment’s pricing structure presents a point of contention, with a $95 total for chicken parmigiana, penne alla vodka, added shrimp, a side of broccoli, and a single glass of Cabernet Sauvignon noted. Portions of the chicken parmigiana and penne alla vodka were described as average, and the addition of five shrimp incurred a $9 surcharge.

Past experiences with the penne alla vodka, a historically favored dish, have seen a decline in flavor. Similarly, the shrimp, once notably seasoned, arrived unseasoned on recent visits. One patron recounted an online order pickup where the individual collecting the order was met with an unwelcoming demeanor.

Despite these observations, some patrons report excellent experiences, citing fresh ingredients and well-prepared pizza and pasta dishes. Calamari was singled out as some of the best encountered. Drink specials were also highlighted positively, with one diner finding the overall bill reasonable upon review, though complimentary bread is not provided.

Andy Boys Pizza
Neighborhood Slice
2
Andy Boys Pizza
83.47
Score
3916 Portsmouth Blvd A4, Chesapeake, VA 23321, USA

Andy Boys Pizza offers a serviceable, albeit uninspired, neighborhood pizza experience. The Andy Boys Special arrived with a notable quantity of mushrooms. Garlic knots, served prior to the pizza, were a textural highlight.

The crust on the pizza provided a crisp foundation, a contrast to the plentiful toppings. A pastrami sandwich demonstrated a competent execution of a deli staple, and mozzarella sticks were notably brittle.

Service from Lindsay and Joanna was efficient and accommodating, even during busy periods. Homemade ranch dressing, described as having an ideal balance of flavors, accompanied the dishes.

Windy city pizza chesapeake
Chicago Style
3
Windy city pizza chesapeake
82.17
Score
480 Kempsville Rd, Chesapeake, VA 23320, USA

Windy City Pizza offers a deep-dish pie with a sauce layered atop a crust browned to a golden hue. The pizza arrives at least an inch and a half thick, presenting a substantial slice. Cheese stretches from the pie with each lifted portion, a lengthy, satisfying pull. The tomato chunks within the sauce and the inclusion of ham and Italian sausage stand out.

The personal pizzas provide an appropriately sized option, with enough remaining for a second meal. Among the varied offerings, the deep-dish preparation warrants attention. The thick mozzarella beneath the red sauce becomes apparent when a fork cuts through.

On one occasion, a delivery issue involving a third-party courier prompted the restaurant to offer a replacement order and a gift card. The subsequent replacement pizza arrived hot and was deemed satisfying.

Frank's Pizza
Pepperoni Dip
4
Frank's Pizza
80.71
Score
2544 Bainbridge Blvd B, Chesapeake, VA 23324, USA

Frank's Pizza is situated at 2544 Bainbridge Boulevard. The establishment offers a particular version of pepperoni pizza. On one occasion, a reviewer received a pizza where the pepperoni grease could be dipped from the crust.

The house salad, a straightforward assembly of lettuce, tomatoes, and onions, was paired with a notably good house dressing. This offering was part of a meal that aimed for simplicity.

The pepperoni pizza crust presented a textural contrast, crisp on the exterior yet yielding within. The sauce and cheese were reportedly well-balanced with an abundant layer of pepperoni.

Yianni's Neighborhood Pizzeria and Family Restaurant
Neighborhood Staple
5
Yianni's Neighborhood Pizzeria and Family Restaurant
80.10
Score
940 Cedar Rd #106, Chesapeake, VA 23322, USA

Yianni's offers a straightforward approach to Italian-American fare. The fried calamari arrives with a crisp exterior, avoiding the rubbery texture common elsewhere, and the accompanying cocktail sauce possesses a house-made quality. The gyro sandwich features moist, flavorful meat, while the shrimp scampi, cooked precisely, benefits from a Parmesan-free preparation. Baklava, served warm, leans towards dryness and presents a firm texture.

Service at Yianni's is attentive, with staff like Eileen noted for their diligent attention and friendly demeanor. The owner makes rounds to ensure patron satisfaction, contributing to a welcoming environment. The establishment maintains a notable cleanliness.

The Veal Parmesan, paired with a robust meat sauce, delivers a substantial portion and ample flavor. Similarly, the spaghetti and meatballs entree stands out with its hearty meat sauce. The BLT sandwich offers a well-executed club-style composition.

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