Jester's Double D Pizza

Located in the heart of Waukegan, Illinois, Jester's Double D Pizza is a must-visit destination for lovers of hearty, Chicago-style pizza and classic American bar & grill fare. This vibrant spot marries the rich tradition of deep-dish and double-decker pizzas with a friendly, welcoming atmosphere that captures the essence of a local favorite—perfect for families, groups, or anyone craving substantial, mouthwatering comfort food.

Jester's Double D Pizza is renowned for its inventive and generously layered pizzas that satisfy even the most voracious appetites. Signature dishes like the Triple Cheese Double-D and the legendary Double Decker Cheese Pizza dazzle with layers of melted mozzarella, savory sausage, and spicy pepperoni stacked to perfection. The inventive Double Decker Sausage and Pepperoni and Meat Lovers – Double Decker elevate traditional pizza with hearty fillings between two crust layers, creating an indulgent feast that's as visually impressive as it is delicious.

For those seeking a flavor-packed twist, the Bomber stands out: Italian sausage steeped in robust marinara, blanketed by cheese—a perfect harmony of bold and comforting. Meanwhile, fans of lighter crusts can enjoy the savory Thin Crust with Bacon or the playful Hawaiian Pizza, combining smoky ham and pineapple for a sweet and salty balance. The menu also excels beyond pizza, offering juicy burgers like the signature Double "D" Burger and Fries, which comes adorned with marinara, mushrooms, oregano, and melted mozzarella cheese—a hearty bite full of complex flavors.

Start your meal with golden, crispy appetizers such as the Jalapeño Poppers bursting with creamy cheese, or the addictive Fried Pickle Spears with a tangy crunch that pairs perfectly with a cold drink from the bar. Sandwich lovers will appreciate the substantial Italian Beef & Sausage Combo served with rich au jus, a local favorite that makes every bite linger with satisfaction.

The atmosphere inside Jester’s echoes a genuine neighborhood feel—warm, inviting, and a little unpretentious. Holiday decorations and festive music, like the Christmas tunes that delighted one visitor, add a homey, joyous touch that makes every visit feel special and memorable. Although some visitors have noted a “locals-only” vibe, many appreciate how this unique character gives the restaurant its authentic charm and welcoming spirit.

Customers repeatedly highlight the quality, abundance, and freshness of the food. One guest fondly described a deep-dish pizza so thick and satisfying it easily feeds four hungry diners, while another raved about dreaming of the pizza weeks after their visit. The double-decker pizzas come praised not only for their taste but also for their generous portions and perfectly crisp crust, offering incredible value—and enough leftovers to savor later. Staff are frequently applauded for their friendliness and willingness to offer informed recommendations, adding to the overall seamless dining experience.

In sum, Jester's Double D Pizza is a hidden treasure in Waukegan, boasting a menu that delights both traditionalists and adventurous eaters alike. Whether you're in the mood for the iconic deep-dish, a towering double-decker marvel, or satisfying bar & grill classics, this gem delivers bold flavors, comforting textures, and an authentic ambiance that leaves a lasting impression. For those craving an indulgent meal served with warmth and character, Jester’s Double D Pizza is worth every bite.