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Milwaukee's best

Chocolate sandwich spots

A savory sandwich followed by a bit of chocolate creates the balance between lunch and dessert.

Based on 690 Opinions
+687
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Updated May 2026
01
Roast Coffee Company image 1
Roast Coffee Company image 2
Roast Coffee Company image 3
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Small coffee shop with exposed cream-city limestone brick and simple creative woodwork creates a cozy, intimate atmosphere. Rotating local artwork and impeccable music playlists add to the great vibes. Frequented by people who appreciate a chill spot with ample outlets for work or meetings.

Hot chocolate stands out for its rich flavor and quality ingredients like Ghirardelli chocolate. Signature drinks include a white chocolate caramel coffee that blends chocolate and coffee smoothly.

Breakfast sandwiches stand out with options like the Radio Milwaukee and 414 sandwich. Bagel sandwiches pair well with a sweet matcha latte or coffee.

People are saying

"I thought the coffee here was the best I've ever had."

"It's a great work-friendly spot for studying or getting work done."

"I made the best hot chocolate in the world."

Good to know

1

Roast Coffee offers a pop-up kiosk at various events throughout the year.

2

The coffee bar is a popular feature at weddings and special events.

3

Roast provides cold brew kegs for events, perfect for large gatherings.

02
SmallPie image 1

Small cafe with cute indoor and outdoor seating, including a covered patio surrounded by plants for sale. Atmosphere feels relaxed and inviting, with a quiet outdoor area that welcomes dogs. The space offers a charming, neighborhood vibe ideal for casual stops.

Chocolate desserts feature a chocolate shortbread crust with a baked fudge layer and chocolate cream filling. The Milwaukee Mud Pie combines crushed chocolate sandwich cookies, whipped cream, and a rich chocolate mousse pie adds a smooth texture.

Sandwiches feature interesting combinations like cheddar and apple or blueberry turkey. Options include breakfast sandwiches and a bacon biscuit sandwich that stands out for flavor.

People are saying

"I found the pies here to be so delicious."

"I loved the blueberry turkey sandwich; it became my favorite."

"The chocolate pie crust and fudge layer had an excellent texture."

Good to know

1

Parking can be challenging in the area, so plan accordingly.

2

Hand pies are priced at $10 each, which may be considered expensive.

3

SmallPie is dog-friendly, allowing pets on the outdoor seating.

03
Vendetta Coffee Bar image 1

Space includes upstairs and downstairs seating with art deco decor and outdoor seating. Atmosphere blends live jazz music with warm lighting, creating a vibe that suits both productivity and relaxation. Frequented by those enjoying espresso martinis, cocktails, and a mix of coffee and food options.

Chocolate appears in drinks and pastries with rich and creamy textures. The hot chocolate and chocolate gelato stand out, alongside a chocolate brioche and a specialty coffee with mint and chocolate.

Caprese and cappuccino sandwiches offer distinctive flavors and satisfy well. Breakfast sandwiches come at full price even when ingredients are missing.

People are saying

"I found the coffee drinks to be absolutely delicious."

"I got the coffee and hot chocolate, it was superb."

"The caprese sandwich was delicious and amazing."

Good to know

1

Espresso martini hour is a popular event at Vendetta Coffee Bar.

2

They host intimate cocktail experiences during after-hours events.

3

Cribbage leagues are held throughout the year for enthusiasts.

04
Casera Cafe & Bakery image 1

Bright, spacious cafe with natural lighting and indoor-outdoor seating creates a calm, relaxing atmosphere. The space feels open and well-curated, suitable for working alone or socializing. Attention to detail and friendly vibe make it welcoming and enjoyable.

Chocolate croissants stand out as a highlight, rated very highly and considered a favorite pastry. Hot chocolate tends to be mild and sometimes requires extra chocolate to boost its flavor.

Baked bread comes out supple yet crisp, making sandwiches stand out. Options include the Melt Beef, Chicken BLT, and Millie Cheesesteak**, all well made with attentive service checking in on orders.

People are saying

"I enjoyed the coffee; it was perfectly made."

"You have to try the chocolate croissants; they're the best I've had."

"The sandwiches here are excellent and mouth-watering."

Good to know

1

The food side of the kitchen closes an hour before the cafe closes.

2

They provide super strong WiFi, making it a good spot for work.

3

Expect a long line on weekends, especially around noon.

05
Gather Bakehouse | Bay View image 1

Bakery space feels plain and dark with a full-blown espresso machine inside. Atmosphere suits an upper-class clientele with limited selection but high-quality croissants and cheese pockets. Energy is calm, focusing on fancy cakes and vegan options.

Chocolate treats include a chocolate-glazed yeast doughnut and a Chocolate Choux pastry that stands out. The chocolate croissant and chocolate-filled cheesepocket add rich, fresh flavors to the selection.

Offers vegan sandwiches and hot ham rolls on Sundays. Sandwiches include options like the Canfora Chop and come with locally made sides such as tots and lumpia. To-go sandwiches provide a quick and tasty lunch option.

People are saying

"I thought the donuts here were the best in town."

"I loved my chocolate-filled croissant; it was perfection."

"The vegan hot ham sandwich reminded me of childhood."

Good to know

1

The ham and rolls are only available on Sundays.

2

Parking may be tricky during events like the Milwaukee Marathon.

3

Vegan items, including sandwiches, are available during Vegan Dining Week.

06
Leon's Frozen Custard image 1

Classic roadside custard stand with vintage 1950s neon signage and a nostalgic diner vibe. Atmosphere feels casual and homey, often enjoyed outside in a parking lot setting with friends and family. Known for best-in-area frozen custard, especially butter pecan and blue moon flavors.

Chocolate appears in several forms like frozen custard cones, sundaes with warm caramel and chocolate toppings, and rich malts. Classic flavors include chocolate and butter pecan, often combined for a creamy, sweet treat.

Spanish hamburger sandwich stands out with its seasoned, sloppy-joe style and has a cult following. Affordable options include grilled cheese sandwiches and hot dogs, both priced under $3.

People are saying

"I thought the ice cream here was the best I've ever had."

"I enjoyed the creamy sweet custard with chocolate toppings."

"The frozen custard is delicious and rich."

Good to know

1

Parking might be tricky because it can get pretty busy.

2

Expect long lines, but wait times are usually short.

3

There is no inside seating; enjoy your treat outside.

07
Gilles Frozen Custard image 1
Dessert restaurant

Small ice cream shop with an old carhop vibe and nostalgic atmosphere that feels like stepping back in time. Busy and cozy space offers both indoor and outdoor seating, creating a classic ice cream shop energy. Known for being a local staple with a friendly, welcoming environment.

Chocolate appears in several forms here, including smooth custard, Oreo mix-ins, and a super chocolate yogurt in a crunchy waffle cone. Fresh pints or quarts of chocolate or chocolate blends offer a rich, creamy experience.

Grilled chicken sandwiches come with thin slices of chicken and fresh tomatoes. Fries often accompany the sandwiches, making a solid combo.

People are saying

"I found the burgers here to be delicious and great."

"I loved the smooth and creamy chocolate custard."

"I thought the grilled chicken sandwich was the very best."

Good to know

1

Gilles Frozen Custard has been in business since 1938, showcasing their experience.

2

Catering services are available for events, accommodating up to 150 people.

3

Parking is plentiful, even during busy times like Saturday nights.

08
Sweet Joy Brazilian Cafe image 1

Cafe blends cozy tropical decor with lush plants and inviting seating, including a swinging chair. Atmosphere feels welcoming and relaxed, suitable for casual visits or remote work. Brazilian cultural touches create a unique vibe distinct from typical cafes.

Chocolate desserts include a Chocolate Mousse Brigadeiro with three cake layers, white chocolate, and chocolate crรจme. Pastries and chocolates stand out, often paired with drip coffee.

Options include a club sandwich served hot and a chicken sandwich paired with black coffee. The chicken sandwich features cheap bread and dry chicken, accompanied by six chips.

People are saying

"I thought the coffee here was delicious and amazing."

"Marcia carefully wrapped the chocolate dessert, preventing transfer."

"The atmosphere here is so inviting and cozy, I could stay all day."

Good to know

1

The cafe offers traditional Brazilian delicacies like pรฃo de queijo and coffee cake.

2

Expect a fun atmosphere during weekend buffet nights.

3

The cafe is suitable for remote work with available wifi.

09
Grace Coffee Co. image 1
Coffee shop

Coffee shop offers a retro feel with green colors and DIY style decor. Atmosphere is lively with music like a nightclub and plenty of natural light. Various seating options include an outdoor patio and a giant butterfly swing.

Almond chocolate croissants come out very rich and delicious, scoring high on flavor. Chocolate in cookies like the peanut butter one is minimal and lacks strong taste or aroma.

Breakfast sandwiches come on an everything croissant with sausage and cheesy hash browns. Portions are big enough to share. Regular sandwiches look great and all options are flavorful.

People are saying

"I thought the coffee here was good."

"The croissant sandwiches here are huge and super tasty."

"The chocolate almond croissant was so rich and delicious."

Good to know

1

Expect busy hours during weekends, especially on opening day.

2

Cleanliness issues have been reported, with tables often unclean.

3

The cafe offers a variety of beverages and food for non-meat diets.

10
Aladdin image 1
Middle Eastern restaurant

Middle Eastern food stall inside a bustling public market offers fresh, bright flavors with a wide choice of meat and vegetarian options. The atmosphere is lively and busy, attracting people looking for quick, healthy meals. Signature dishes include authentic tabouleh and delicious falafel wraps.

Chocolate pistachio and shredded wheat stands out as a seriously yummy treat. Staff make fresh chocolate strawberries by drizzling chocolate on top, though the chocolate at the bottom can harden and strawberries may drain liquid.

Falafel sandwiches come with Kalamata olives and various sauces. Options include a veggie falafel wrap alongside the sandwich.

People are saying

"The falafel here is fresh, warm, and flavorful."

"I thought the chocolate strawberries were fire and reasonably priced."

"The falafel sandwich comes with fresh, deep green tabouleh and baba ganouj."

Good to know

1

Aladdin offers a wide choice of meat and vegetarian options.

2

Smoothies are made fresh on the spot with quality ingredients.

3

Prices are reasonable, with meals around $10.

11
Brisa Do Mar image 1
Italian restaurant

Upscale Italian restaurant with riverside patio and bright, airy dining room offers a peaceful water view and live Italian soprano music. Guests arrive by boat or on foot, enjoying a contemporary style that blends classic and creative dishes. The atmosphere stays welcoming and classy, suited for relaxed dinners or special occasions.

Desserts feature bitter chocolate with creative presentations like a birds nest chocolate raspberry sculpture and a chocolate espresso cake.

Chicken parmesan sandwich stands out for its size and flavor, enough for two meals. The steak sandwich and meatball sandwich also deliver rich, well-cooked flavors without sides included.

People are saying

"The pizza here is amazing, especially the wood-fired kind."

"The chicken parmesan sandwich was delicious and large."

"I capped off my meal with the divine chocolate espresso cake."

Good to know

1

Reservations are recommended during events to avoid inconvenience.

2

Fashion shows and house music events are hosted regularly.

3

Gluten-free pasta options are available, but may vary seasonally.

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