Windy city pizza chesapeake Menu

4.3
(950+ Reviews)
  • Dinners

    • Lasagna

      Layer upon layer of fresh Italian sausage, ground beef, ricotta, parmesan & mozzarella cheese... includes garlic bread
      $14.89
    • Chicken Parm Dinner

      Two boneless breaded chicken breasts, smothered in red sauce and topped with mozzarella cheese. Served over spaghetti... includes garlic bread
      $18.34
    • Spaghetti

      With your choice of Italian sausage or two meatballs... includes garlic bread
      $16.04
  • Sandwiches

    • Cheesy Beef

      Italian beef smothered in mozzarella cheese. Served with chips - Substitute fries for $1.50
      $12.59
    • Meatball Sand

      A delicious blend of beef, pork, two types of Italian cheeses, garlic & spices topped with red sauce & mozzarella. Served with chips - Substitute fries for $1.50
      $12.59
    • Italian Sausage Sand

      A fresh mild link topped with red sauce and sweet peppers. Served with chips - Substitute fries for $1.50
      $9.14
    • Gyros

      Beef & lamb shaved fresh off the spit, tzatziki sauce, onions & tomatoes on warn pita bread. Add feta for $1. Served with chips - Substitute fries for $1.50
      $11.44
    • Chicken Parm Sand

      Fried split chicken breast smothered in red sauce and topped with mozzarella cheese. Served with chips - Substitute fries for $1.50
      $11.44
    • The "Ditka" Combo

      Da Coach's Favorite!! Italian beef piled high on top of an italian sausage link. Served with chips - Substitute fries for $1.50
      $17.19
    • Chicago Hot Dogs (2)

      $11.44
    • Italian Beef

      A Chicago Southside original! Beef "imported" from Chicago, slow cooked in Italian seasonings, thinly sliced & drenched in its own juices, piled high on French bread and toped with sweet peppers. Giardiniera served on request for $0.50. Served with chips - Substitute fries for $1.50
      $11.44
    • Chicago Hot Dog

      Authentic Vienna beef "dragged through the garden" on a a poppy seed bun. For our East coast friends, the garden includes: mustard, relish, onions, tomatoes, pickle spear, sport peppers and celery salt. Served with chips - Substitute fries for $1.50
      $6.27
  • Beverages

    • 2 Liter Dr Pepper

      $4.54
    • 2 Liter Mountain Dew

      $4.54
    • 2 Liter Pepsi

      $4.54
    • 2 Liter Diet Pepsi

      $4.54
    • Bottled Water

      $2.59
    • Other Drink

      $4.03
  • Appetizers

    • Breadsticks

      Served with marinara
      $5.69
    • Lays Potato Chips

      $1.67
    • Chicken Wings- Half Dozen

      Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot or Naked. Served with ranch or bleu cheese
      $9.14
    • Sausage Bombs

      Large garlic Italian sausage chunks tossed in hot sauce and served with ranch
      $7.99
    • Garlic Bread

      $4.54
    • Seafood Dip

      Real crab & shrimp (not surimi) blended with aged parmesan & spices. Served with fried pita chips
      $12.59
    • Sampler Platter

      Create your own combo with your choice of Planks, Poppers, Pickles, Fritters, Sausage Bombs & Wings . Choose 3 or 4
      $13.74
    • Corn Fritters

      Deep fried and slightly spicy. Filled with corn, cream cheese & bacon. Served with ranch
      $9.14
    • Chicken Wings -Dozen

      Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot or Naked. Served with ranch or bleu cheese
      $17.77
    • Mozzarella Planks

      Served with marinara
      $9.14
    • Southwest Eggrolls

      Crisp flour tortillas filled with chicken, corn, black beans, and peppers. served with sweet chili sauce.
      $11.44
    • Crinkle Cut Fries

      $4.54
    • Fried Pickle Spears

      Served with ranch
      $7.99
    • Cheesy Garlic Bread

      $6.84
    • Cheddar Jalapeno Poppers

      Serve with sweet chili sauce
      $9.14
    • Loaded Fries

      A heaping mound of fries topped with real bacon, melted cheddar cheese & sour cream
      $10.29
    • Cheesy Breadsticks

      Served with marinara
      $6.84
      Cheesy Breadsticks
    • Pizza Puff

      Hand-folded flour tortilla stuffed with cheese, sausage, pizza sauce and spices, then deep fried to perfection!
      $5.69
    • Buffalo Chicken Dip

      Made in house! Creamy buffalo chicken dip(shredded chicken, buffalo sauce, ranch, cheddar and cream cheese) served warm with seasoned pita chips
      $10.29
  • Pizza

    • Thin Crust

      Chicago's most popular pizza! Square cut - Signature Blend of 4 Natural Cheeses
      $11.44
    • Heart Attack

      Our deep dish crust topped with pepperoni, fresh Italian sausage, diced ham & beef
      $36.74
    • Michigan Ave

      Our thinl crust topped with mushrooms, bell peppers, onions & black olives
      $16.04
    • Windy City Special

      Our deep dish crust brushed with garlic & oil. Extra portions of fresh Italian sausage & fresh baby spinach
      $35.59
    • Maxwell St

      Our thin crust topped with white sauce, seasoned steak, bell peppers, onions & plenty of cheese
      $16.04
    • Stony Island

      Our thin crust topped with Sweet Baby Ray's BBQ Sauce, chicken & bacon
      $16.04
    • Southside Special

      Our deep dish crust topped with pepperoni, Italian sausage, mushrooms, green peppers & onions
      $37.89
    • Pulaski

      Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
      $17.19
    • BBQ Chicken & Bacon

      Our deep dish crust loaded with diced chicken breast, real bacon & smothered with Sweet Baby Ray's BBQ sauce
      $34.44
    • Clark St

      A thin crust white pizza - White sauce, fresh spinach, tomato slices & olives
      $16.04
    • Cicero

      Our thin crust topped with pepperoni, fresh Italian sausage, mushrooms, bell peppers & onions
      $18.34
    • Deep Dish

      The famous Chicago pie with the sauce on top! Please allow 45 minutes bake time... It's worth the wait!! Add garlic butter to the crust for $1.50
      $13.74
    • Gluten-Free

      $18.34
  • Salads

    • Family Antipasto Salad

      $25.24
    • Individual Antipasto Salad

      Genoa salami, diced ham, black olives, banana peppers, provolone cheese & shredded mozzarella with your choice of dressing.
      $7.99
    • Family Garden Salad

      $20.64
    • Family Greek Salad

      $25.24
    • Individual Garden Salad

      Roma tomatoes, black olives, cheddar cheese & croutons with your choice of dressing. Add diced chicken for $2/$6
      $6.84
    • Individual Greek Salad

      Roma tomatoes, black olives, diced onions & feta cheese with your choice of dressing
      $7.99
  • Dessert

    • Brownie

      $4.31
    • Cake

      $9.14
    • Vanilla Cheesecake

      $7.99
    • Specialty Cheesecake

      Made in house.
      $9.14
    • Cookie

      $2.59

Menu Photos

  • Menu 1
  • Menu 2
  • Menu 3
  • Menu 4
  • Menu 5
  • Menu 6

Menu Photos

  • Menu 1
  • Menu 2
  • Menu 3
  • Menu 4
  • Menu 5
  • Menu 6
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(757) 410-5550

480 Kempsville Rd, Chesapeake, VA 23320


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