Windy City Pizza
Windy City Pizza is a pizza restaurant in Red Mill & General Booth, Virginia Beach, located at 1630 General Booth Blvd. Chicago transplants' deep-dish and thin-crust pizzeria on General Booth Boulevard, with ingredients shipped in from home and delivery to NAS Oceana.
Two Chicago transplants brought deep-dish and thin-crust pizza to the General Booth corridor, shipping in ingredients from home to keep the recipes honest. The kitchen delivers as far as NAS Oceana and Dam Neck, covering the southern beaches' need for an actual Chicago-style pie alongside the everyday takeout and dine-in menu.
- Family Friendly
Visit
- Address: 1630 General Booth Blvd, Virginia Beach, VA
- Phone: (757) 689-2270
- Website: https://www.windycityvb.com/
Last verified 2026-07-10.
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While You're in the Area
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Female-owned General Booth-corridor distillery pouring corn-based vodka and the Butterfly Lemon Spritz, with distillery tours and infusion workshops.
Hunt Club Farm
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General Booth wing institution since 1987 — award-winning sauces, 15-plus craft taps, and wall-to-wall TVs for game day.
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New Realm Brewing Co.
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Ocean Breeze Waterpark
Ocean Breeze is Virginia Beach's outdoor waterpark, on General Booth Boulevard just down the road from the Virginia Aquarium — you can't miss it, because a…
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Operation Brew Coffee and Bakery
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Upcoming Events Nearby
Cherry Blossom Festival
March 26, 2027 – March 28, 2027 · annual
Virginia Beach Parks & Recreation's spring showcase fills Red Wing Park's cherry tree grove with live cultural performances, martial arts demonstrations, and hands-on crafts timed to peak bloom in late March. The 2026 edition added a first-ever Nighttime Hanami, lighting the blossoms after dark on opening evening before the daytime festival took over the weekend. Admission and parking are free, with an overflow grass field opening for weekend crowds -- a genuinely photogenic, low-key alternative to the Oceanfront festival circuit, along General Booth Boulevard.
Sandbridge Pig Pickin'
September 12, 2026 · annual
The Sandbridge Volunteer Rescue Squad's all-you-can-eat pig roast at Little Island Park has been the neighborhood's signature fundraiser for more than four decades, paying for the advanced life-saving equipment behind the squad's 1,000-plus annual emergency calls. Barbecue, beer and wine, live music, local art vendors, and a bounce house for kids fill the park for an afternoon, with free admission for children under 10. It's Sandbridge at its most neighborly -- a beach-community fundraiser rather than a tourist draw, held at the same park that anchors the south end of the beach.
Virginia Beach Restaurant Week
January 15, 2027 – January 24, 2027 · annual
The Virginia Beach Restaurant Association's flagship dining event fills each January with prix-fixe menus at roughly five dozen restaurants citywide, from Laskin Road institutions to Oceanfront hotel dining rooms. The 2026 edition ran the theme 'Tastes & Traditions, A Culinary Celebration by Land and by Sea,' spotlighting Chesapeake staples like crab, oysters, ham, and peanuts alongside modern reinterpretations. A companion Dine & Stay program bundles discounted rates at more than a dozen partner hotels, making it as much a slow-season visitor draw as a locals' night out. The VBRA runs the event out of its Laskin Road office in Hilltop, the city's densest cluster of independent kitchens.