Milwaukee's Best Calzones

Forget the pizza debate—sometimes you want your favorite toppings folded inside a golden, pillowy pocket of dough.

The greater Milwaukee area delivers a surprising calzone paradise, from legendary deep-fried versions invented in the 1940s to coal-fired Brooklyn imports and authentic Chicago-style turnovers. This comprehensive guide maps out 60+ family-friendly destinations where parents can order confidently and kids can dig into cheesy goodness without utensil struggles.

A great calzone shares three qualities: dough that's crispy outside yet soft within, a generous cheese-to-filling ratio, and a marinara dipping sauce that earns its keep. Milwaukee's Italian heritage—from Brady Street's immigrant roots to generations of neighborhood pizzerias—means calzone excellence spans every corner of the metro area. Whether you're in Waukesha craving a deep-fried Ponza Rotta or exploring Cedarburg's downtown charm, quality calzones await your family.

Milwaukee neighborhoods

The city proper offers everything from New York-style giants to old-world Italian market calzones, with several standout destinations across distinctive neighborhoods.

Bay View anchors the calzone scene

Tenuta's Italian Restaurant (2995 S. Clement Ave., 414-431-1014) earns its "Best Italian Restaurant" title since 2015 with calzones crafted from recipes brought by the founding family from southern Italy in 1961. The cheese calzone starts at $8, with toppings at $1.25 each, while the Calabrian Calzone ($14+) features house-made sausage, calabrian chili, kale, ricotta, and mozzarella. The cozy space fills quickly—reservations are essential. Hours run Tuesday through Sunday, 4-10 PM, with delivery available 4-9 PM.

Classic Slice (2797 S. Kinnickinnic Ave., 414-238-2406) serves football-sized calzones at $15.50, stuffed with ricotta and parmesan blend, garlic, and herbs. Two toppings plus marinara dipping sauce come included. Kids love the arcade games and outdoor seating, while parents appreciate vegan cheese options and locally sourced ingredients. The casual counter-service setup works perfectly for families, with delivery through DoorDash, Uber Eats, and Grubhub.

Rosati's Pizza Bay View (145 W. Oklahoma Ave., 414-489-7191) brings Chicago-style calzones starting at $11.99—crisp-baked turnovers with hand-rolled edges and signature marinara. Add meatballs, chicken breast, or sausage for extra substance. Open daily from 10:30 AM to approximately 9:45 PM with full delivery coverage.

Brady Street and the East Side offer historic Italian options

Glorioso's Italian Market (1011 E. Brady St., 414-272-0540) represents Milwaukee's best calzone value at just $5.99 each. The Spicy Sausage & Pepperoni Calzone features house-made sausage, pepperoni, calabrese, and mozzarella, while the Italian Classic includes mild sausage, bell peppers, onions, ricotta, and mozzarella. This 75-year-old family institution operates a café alongside the market—kids can explore Italian treats, gelato, and bakery items while waiting. Hours run Monday-Friday 9 AM-7 PM, Saturday 8 AM-6 PM, Sunday 8:30 AM-5 PM.

Sal's Pizza Eastside (2974 N. Oakland Ave., 414-967-8040) channels Brooklyn roots with New York-style calzones ranging from $13-15. The cheese calzone runs $13, while Pepperoni and Sausage or Ham & Cheese hit $15. They also offer stromboli varieties including Spinach and Feta and Chicken Parmesan at $15-16. Everything's made in-house using local ingredients. Open daily 11 AM-10 PM with full dine-in, carryout, and delivery options.

Pizza Shuttle (1827 N. Farwell Ave., 414-289-9993) operates as a Milwaukee institution since 1985, now employee-owned and serving calzone pinwheels—homemade dough rolled with mozzarella and toppings, cut into sections, and basted with garlic butter. Open until 3 AM daily, this spot features pinball machines, arcade games, Zoltar, and a jukebox that keeps kids entertained. Free parking and elevator access make family visits smooth. A second location operates at 3rd Street Market Hall downtown.

West side and south side round out city options

Di Stefano's Pizza Palace (4630 W. Forest Home Ave., 414-321-9600) has served the Jackson Park neighborhood since 1972 with everything made from scratch daily. This carryout-focused spot (no dine-in) operates Tuesday through Saturday, 3-10 PM, with delivery zones covering much of the south and west sides. Curbside pickup available.

Pizzeria Scotty (9022 W. Oklahoma Ave., West Allis, 414-543-1300) specializes in genuine Chicago-style with multiple crust options. Known for Chicago pan pizza and stuffed varieties, the restaurant excels at authentic Italian beef sandwiches alongside their pizza and calzone offerings. Open Monday-Thursday 11 AM-10 PM, Friday-Saturday until 11 PM, Sunday 11 AM-10 PM. Carryout and delivery only—no dine-in seating.

North Shore communities

The affluent North Shore delivers quality over quantity, with Fox Point emerging as the calzone capital for Shorewood, Whitefish Bay, and surrounding communities.

Fox Point leads with two excellent options

Rosati's Pizza Fox Point (6900 N. Santa Monica Blvd., 414-251-2051) serves Chicago-style cheese calzones at $11.75, customizable with any pizza ingredients. The crisp-baked Italian turnover arrives with marinara dipping sauce. Kids' menu items include affordable jumbo slices ($4) and combo deals. Open daily 11 AM-8:30 PM with DoorDash, Uber Eats, and Slice delivery.

Calderone Club Foxpoint (8001 N. Port Washington Rd., 414-352-9303) offers scratch-made calzones using traditional family recipes from the owners' mother. The restaurant also features their unique "Calabrian Crust" pizza and famous fried eggplant strips. This welcoming family spot serves Tuesday-Thursday 4-9 PM, Friday-Saturday 4-10 PM, Sunday 4-8 PM—closed Mondays. Reservations recommended (90-minute table limits apply). Online ordering through ZenFoody.

Shorewood and Glendale add accessible options

Falbo Bros. Pizza Shorewood (2213 E. Capitol Dr., 414-964-5560) combines NY thin crust and Chicago deep dish inspirations with hand-rolled fresh dough made every few hours. Their "Pick 6 Pizza" at $15.50 with six toppings demonstrates generous portioning that extends to their Italian menu. Available on Grubhub with carryout and delivery.

Jet's Pizza Glendale (6813 N. Green Bay Rd., 414-533-0082) offers Detroit-style specialties including calzone-style Deli Boats. Famous for their 8-corner crust with caramelized cheese edges, Jet's provides free flavorized crust options—Turbo Crust, butter, romano, and more. Open Sunday 11 AM-10 PM, Monday-Thursday 10 AM-10 PM, Friday-Saturday 10 AM-11 PM. Mobile app ordering earns 15% off menu-priced pizza.

Western suburbs

Waukesha County delivers Milwaukee's most unique calzone experience alongside reliable chains and upscale newcomers.

Jimmy's Grotto invented the Ponza Rotta

Jimmy's Grotto (314 E. Main St., Waukesha, 262-542-1500) demands a family pilgrimage for their legendary Ponza Rotta—a deep-fried calzone invented here in the 1940s by original co-owner Rosie Ruccia. Starting around $4.50 for cheese, these crispy golden pockets come stuffed with sauce, cheese, and customizable toppings including Italian sausage, pepperoni, Canadian bacon, mushrooms, and jalapeños. The counter-service format—order up front, sit anywhere—works perfectly for families. Operating since 1946 as Waukesha's oldest pizza restaurant, Jimmy's draws visitors from across the state seeking this unique creation. Open Sunday-Thursday 11 AM-10 PM, Friday-Saturday 11 AM-11 PM. DoorDash delivery available.

Brookfield delivers upscale and casual variety

Grimaldi's Pizzeria (20119 N. Lord St., The Corners of Brookfield, 262-785-1115) brings Brooklyn's coal-fired tradition to Wisconsin. Their calzones ($18.70+) bake in a 25-ton coal-burning oven, producing charred perfection stuffed with ricotta, oregano, black pepper, romano, and fresh parsley. The century-old secret-recipe sauce completes the experience. This 4,700-square-foot space seats 102 indoors plus 45 on the patio—dogs welcome outside. Red-and-white gingham tablecloths establish the classic New York vibe. Open Monday-Thursday 11 AM-9 PM, Friday-Saturday 11 AM-10 PM, Sunday 11 AM-9 PM.

Glass Nickel Pizza Co. Brookfield (13175 W. Bluemound Rd., 262-782-8000) offers excellent value with their weekly Calzone & Individual Salad special at $15. This community-focused, locally-owned chain (established 2008) uses in-house delivery teams—no outsourcing. Their "Pizza with Purpose" charitable program resonates with families. Open daily 10 AM-9 PM with delivery covering Brookfield, Elm Grove, Wauwatosa, New Berlin, and parts of West Allis and Milwaukee.

Riverfront Pizzeria Brookfield (near Metro Market on Bluemound and Calhoun Roads) uses wood-fired cooking for their calzones and strombolis, creating distinctive charred flavor and crispy crusts.

Rosati's blankets Waukesha County

Rosati's Pizza maintains multiple Waukesha County locations serving identical Chicago-style calzones—crisp-baked Italian turnovers with hand-rolled edges, mozzarella, and signature marinara:

• Waukesha (310 W. St. Paul Ave.) - Original toppings include sausage, pepperoni, ground beef, Canadian bacon, Italian beef, bacon, grilled chicken, mushroom, onion, green pepper, fresh garlic, tomato, spinach, jalapeños, olives, banana peppers, hot giardiniera, and pineapple

• Pewaukee (690 Westfield Way, 262-695-4080)

• Oconomowoc (1320 Pabst Farms Circle, Suite 110, 262-200-0066)

• Menomonee Falls (N81W15086 Appleton Ave., 262-250-3333)

All locations offer dine-in, carryout, curbside pickup, and delivery through Slice.

Additional western suburb destinations

Giuseppe's Pizzeria (615 Main St., Delafield, 262-337-9800) serves signature thin-crust pizza with Wisconsin whole-milk mozzarella and sweeter sauce. Their Italian menu includes customizable options. Open Sunday 11 AM-8 PM, Monday 4-8 PM, Wednesday-Thursday 4-8 PM, Friday 3-9 PM, Saturday 11 AM-9 PM—closed Tuesdays. Outdoor seating welcomes dogs.

Papa Murphy's locations in New Berlin (3830 S. Moorland Rd.), Oconomowoc (528 E. Wisconsin Ave.), and Menomonee Falls (W156N5530 Pilgrim Rd.) offer take-and-bake calzones—"lightly crispy outside, hot melty deliciousness inside" that families bake fresh at home. The Mini Murph kids' meal provides a make-and-bake pizza kit perfect for young chefs. SNAP EBT accepted.

Northern suburbs deliver hidden calzone gems

Ozaukee and Washington Counties feature family-owned pizzerias serving generous portions at reasonable prices.

Mequon and Cedarburg anchor Ozaukee County

Leonardo's Pizza (11051 N. Port Washington Rd., Mequon, 262-241-8557) has served families for over 30 years with homemade New York-style calzones. Pricing starts at $7.95 for cheese, with specialty calzones at $9.85—Italian Sausage with Peppers & Onions, Spinach & Pepperoni, Veggie, and the Leo Special (ham, turkey, salami). Extra toppings run 85¢ each. Open Tuesday-Thursday 11 AM-9 PM, Friday-Saturday 11 AM-10 PM, Sunday 2-9 PM—closed Mondays. Delivery covers Mequon, Thiensville, Bayside, and River Hills.

Sal's Pizza Cedarburg (W63 N635 Washington Ave., 262-375-0011) brings Brooklyn authenticity to charming downtown Cedarburg. Calzones run $13-16—cheese at $13, Pepperoni and Sausage at $15, Ham & Cheese at $14. Stromboli options include Sausage and Pepperoni Roll ($15), Chicken Parmesan ($16), and Spinach and Feta ($15). Everything made fresh in-house. Open Sunday-Thursday 11 AM-9 PM, Friday-Saturday 11 AM-10 PM.

Downtown Pizza (227 S. Main St., Thiensville, 262-387-4992) earned Neighborhood Favorite awards five consecutive years (2017-2023) with fresh handmade dough and Wisconsin cheeses. Gluten-free options available. Family-owned since January 2022 with 12-15 table seating. Open generally 3-8 PM or 3-9 PM—call ahead to confirm.

Tomaso's (W63N688 Washington Ave., Cedarburg, 262-377-7630) represents Cedarburg's iconic pizza destination since the 1970s, earning Milwaukee Magazine's Best Pizza and Ozaukee County Best Pizza honors. Their unique style puts cheese under the sauce on a crispy, cracker-like thin crust. While calzone selection is limited, the hand-rolled sausage and homemade sauce justify a visit. Open Tuesday-Saturday 11 AM-8:30 PM—closed Mondays.

Washington County offers excellent variety

Michaleno's Pizzeria operates three locations—Saukville (234 E. Dekora St., 262-235-4842), West Bend Main Street (235 S. Main St., 262-429-1000), and the original. Family-owned since 2008 by Mike and Debbie Herbert and their four sons, reviewers describe the calzones as "calzone heaven" and "incredible." Specialty items include Gyro Pizza, Meatball Marinara, and Blanket Pizzas (double-stuffed crust). The West Bend location offers dine-in; Saukville is carryout and delivery only. Delivery runs $3 with $20 minimum.

Sal's Pizzeria West Bend (161 N. Main St., 262-384-5314) earns rave reviews claiming "best pizza and calzones in Wisconsin" with "true East Coast flavor." All calzones include mozzarella and ricotta cheese plus two complimentary garlic knots and marinara sauce. Varieties include Build Your Own, Supreme (sausage, pepperoni, green peppers, mushrooms, onions, black olives), Spinach & Feta, and Gyro Calzone with tzatziki sauce. Open Monday-Tuesday 11 AM-8 PM, Wednesday-Saturday 11 AM-10 PM, Sunday 11 AM-8 PM.

Brama's Pizzeria (N112W16700 Mequon Rd., Germantown, 262-735-4602) operates under the motto "It's All In The Sauce" with a chef boasting 45+ years of restaurant experience. Calzones appear on their extensive Italian menu alongside pasta and specialty pizzas. Room rental available for parties. Open Tuesday-Sunday (closed Mondays)—dine-in and carryout only, no delivery.

De Marinis Pizzeria (N88W15229 Main St., Menomonee Falls, 262-253-1566) offers Italian dining with a free banquet room accommodating 100-125 people—perfect for celebrations. The game room features pool, darts, and Golden Tee. Known locally for the best Friday Fish Fry in town. Open Monday-Thursday and Sunday 4-9 PM, Friday 11 AM-10 PM, Saturday 4-10 PM.

Maricio's in Barton (1726 Barton Ave., West Bend) serves calzones in small and large sizes with any pizza toppings. Their unique "Underground" basement dining room with bar hosts private parties. The self-service format—seat yourself, order at bar, pay when ready—keeps things casual.

Southern suburbs feature Italian institutions and hidden gems

The south side's working-class roots produced several multi-generational Italian restaurants alongside newer family favorites.

Oak Creek and Franklin deliver diverse options

Marco's Pizza Oak Creek (111 E. Forest Hill Ave., 414-764-3330) serves legendary "Rollos"—extra-large calzone-style creations including the "EBA Rollo" (Everything But Anchovies). Reviewers describe them as "three times the size of a normal calzone" at approximately $10 each. This family operation has served homemade recipes since 1959, earning three Milwaukee Magazine nominations. Primarily carryout with delivery to Franklin, Oak Creek, and South Milwaukee.

Rosati's Pizza Franklin (6558 S. Lovers Lane Rd., 414-529-1400) offers cheese calzones at $11.00 with a Wednesday special dropping the price to $7.95. The Chicago-style calzones arrive "crisp baked with hand-rolled edges, stuffed to the brim." Fresh dough made in-house daily. Generous portions suit sharing. Open Tuesday-Saturday 11 AM-10 PM, Sunday noon-8 PM—closed Mondays. Curbside pickup and Slice delivery available.

Greenfield and Greendale serve families well

NiNi's Pizzeria (6131 W. Cold Spring Rd., Greenfield, 414-604-2680) offers calzones starting at $7.95 alongside hand-tossed thin-crust pizza. Yelp verifies "good for kids" with clean interior, cozy atmosphere, and friendly staff. Catering and private party options work for celebrations. Open Monday-Thursday 3-9 PM, Friday-Sunday 11 AM-9 PM. DoorDash delivery plus their own drivers. Health Score: 96/100.

Klasiana Pizza (5487 S. 76th St., Greendale, 414-421-0000) has served families for 18+ years with exceptional deep dish and Chicago thin crust. Fresh dough daily, premium meats, and freshest vegetables define their approach. Calzone varieties include chicken alfredo. Carryout and delivery only—no dine-in seating. Open Wednesday-Thursday 4-9 PM, Friday-Saturday 3-9:30 PM, Sunday 3-8:45 PM. DoorDash and Slice delivery. Health Score: 95/100.

Ricardo's Pizza (5627 Broad St., downtown Greendale, 414-421-1980) occupies a charming spot in Greendale's historic downtown with full bar and traditional Italian ambiance. The 13+ year veteran serves exceptional pizza alongside an extensive Italian menu. Friday Fish Fry draws crowds. Open Monday-Thursday 4-9 PM, Friday-Saturday 4-10 PM—closed Sundays.

Hales Corners maintains Italian tradition

Ann's Italian Restaurant (5969 S. 108th Pl., 414-425-5040) launched in 1969 with just six tables—now 30+ tables serve customers seeking "the best pizza anywhere." While calzones aren't specifically listed, the extensive build-your-own pizza and Italian entrée menu (homemade ravioli, Sicilian-style steak, veal parmigiana, chicken cacciatore) makes this a destination. "Perfect place to take the kids"—dog-friendly outdoor patio, accommodates large groups, gluten-free options available. Open Tuesday-Thursday 5-9 PM, Friday 5-10 PM, Saturday 4-10 PM, Sunday 4-9 PM—closed Mondays.

South Milwaukee and Cudahy honor their heritage

Paisano's Italian Restaurant & Pizzeria (113 N. Chicago Ave., South Milwaukee, 414-856-9020) delivers HUGE portions—reviewers report "dinner for three whole nights" from single meals. This 13+ year family business makes its own deliveries (no third-party apps) and offers the "best thin crust pizza on the south side." The back room accommodates group parties. Open Monday-Thursday and Sunday 11 AM-9 PM, Friday-Saturday 11 AM-10 PM.

Barbiere's Italian Inn (1021 Milwaukee Ave., South Milwaukee, 414-764-1234) originated in 1963 and opened this location in 2009. Famous for "the best garlic bread in Metro Milwaukee"—legendary status. Fresh-made dough daily, fresh stringy mozzarella, and homestyle recipes define the menu. The lasagna dinner includes soup, salad, two garlic breads, and spumoni. Homemade tiramisu and cannoli round out dessert. Open daily 3-8 PM. DoorDash delivery available.

Papa Luigi's Pizza (3475 E. Layton Ave., Cudahy, 414-483-6111) has anchored the community since 1982—nearly four decades of thin-crust excellence. Awards include Restaurant Guru Best Pizza 2024 & 2025 and Best Food Delivery 2021. Kids' Menu comes with coloring pages, crayons, and candy. Banquet facilities handle parties and special events. Full bar with happy hour (BOGO domestic beer, rail liquor, house wine 4-6 PM). Open Monday-Friday 4-10 PM, Saturday-Sunday 11 AM-10 PM.

St. Francis rounds out the south

Saraphino's (3074 E. Layton Ave., St. Francis, 414-744-0303) serves thin and crispy Italian-style pizza with famous homemade sauce. Calzones with one topping start around $7-9—build your own with favorite toppings. Homemade pasta includes ravioli, tortellini, and gnocchi. Hand-breaded chicken parmesan portions are "massive." Kids' Menu available alongside Friday Fish Fry specials. Health Score: 100/100. Slice delivery available.

Regional chains provide reliable family options throughout Milwaukee

Several chains maintain consistent calzone quality across multiple locations, offering convenience when exploring unfamiliar areas.

Rosati's Pizza operates the widest network with locations in Bay View, Fox Point, Franklin, Waukesha, Pewaukee, Oconomowoc, and Menomonee Falls. Their Chicago-style cheese calzones ($11-12) feature crisp-baked crusts with hand-rolled edges, served with marinara dipping sauce. All locations offer dine-in, carryout, and delivery through Slice.

Jet's Pizza brings Detroit-style expertise to Glendale and Brookfield with their calzone-style Deli Boats and signature 8-corner pizzas. The mobile app delivers 15% discounts on menu-priced pizzas. Late-night hours (until 11 PM Friday-Saturday) accommodate families with busy schedules.

Glass Nickel Pizza Co. serves Brookfield and Waukesha with community-focused operations and charitable "Pizza with Purpose" programs. Their $15 calzone-and-salad special provides excellent value, and in-house delivery teams ensure quality control.

Papa Murphy's take-and-bake locations span New Berlin, Oconomowoc, Menomonee Falls, and Grafton—ideal for families wanting fresh-baked calzones at home. SNAP EBT acceptance and Mini Murph kids' kits add accessibility.

Conclusion: Your calzone adventure awaits

The greater Milwaukee area surprises with calzone diversity—from Glorioso's $5.99 market specials to Grimaldi's $18.70 coal-fired Brooklyn imports, with Jimmy's Grotto's legendary deep-fried Ponza Rotta standing alone as a regional original. Families gain several strategic advantages: most pizzerias welcome children warmly, calzones travel well for carryout, and the customizable format lets picky eaters choose exactly what goes inside.

For the signature Milwaukee calzone experience, Jimmy's Grotto in Waukesha demands a dedicated trip—nothing else in the region matches the Ponza Rotta's deep-fried uniqueness. For everyday family dining, Rosati's locations scattered across the metro provide consistent Chicago-style quality with convenient delivery. For Italian market ambiance, Glorioso's on Brady Street combines unbeatable prices with 75 years of tradition. For special occasions, Grimaldi's coal-fired calzones in upscale Brookfield deliver Brooklyn authenticity in an expansive, family-welcoming space.

Most restaurants update hours seasonally and menus periodically—call ahead for large parties or specific dietary needs. The best Milwaukee calzones reward the families willing to explore beyond their immediate neighborhoods, discovering multi-generational Italian traditions still thriving across the region.