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Guide to Chicago

Chocolate milkshakes

Made for those who believe a milkshake is only worth drinking if it is intensely chocolate.

Based on 604 Opinions
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Updated May 2026
01
Esparza’s Tacos image 1
Esparza’s Tacos image 2
Esparza’s Tacos image 3
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Mexican restaurant

Small, cozy space with classic Mexican decor and warm, inviting atmosphere. Music plays fairly loud, creating a casual but lively vibe. The place stays spotlessly clean and offers a welcoming greeting at the door.

Chocolate and banana milkshake stands out as a favorite. Milkshakes come made to perfection with options like strawberry also available.

Chocolate and banana milkshake stands out as a favorite drink. Chocolate appears in various forms like a milkshake that evokes memories, a smoothie mixed with strawberry and banana, and a chocolate ice cream cone that feels natural and satisfying.

People are saying

"The steak tacos here are so flavorful and delicious."

"The Al Pastor's edges had a perfect crisp, like candy for meat lovers."

"The chocolate milkshake brought back memories and had an incredible flavor."

Good to know

1

They open at 9am and close at 12am on weekends and 11pm on weekdays.

2

Prices are somewhat high, aligning with other taco joints in the area.

3

The establishment has no dedicated parking lot.

02
Vegan Now 2 Go image 1
Vegan restaurant

Vegan fast food spot offers relaxed atmosphere with cute decor and great music. Menu features comfort food like jerk tacos and mac and cheese, drawing both vegan and non-vegan crowds. Space feels welcoming and provides a friendly vibe distinct from typical vegan eateries.

Milkshakes come in decent size with a strong strawberry flavor. Whipped cream is not included but would enhance the taste.

Chocolate shakes and chocolate milkshakes appear regularly on the menu. They come alongside various dishes like vegan fish sandwiches and paninis, making chocolate shakes a common choice here.

People are saying

"I found the food delicious, hot, and fresh."

"You have to try the chocolate shake here."

"This milkshake was the best I've ever had."

Good to know

1

The hot bar costs $9.95 per pound.

2

They only accept cash, which may be inconvenient.

3

Credit card payments incur an extra $8 charge.

03
Nube's Ice Cream & Coffee Shop image 1

Small cafe with cozy, homely vibe and friendly atmosphere offers unique fruit ice cream flavors like guava and soursop. Warm interior with limited seating invites quiet enjoyment. Coffee service extends beyond typical hours, adding to its local charm.

Chocolate milkshakes stand out with their creamy texture and rich flavor. The menu includes ice cream-based milkshakes alongside yogurt and iced coffee options.

Chocolate flavors include rum raisin and classic chocolate, both highly praised. Chocolate ice cream comes with whipped cream and shredded cheese, and chocolate milkshakes are also available.

People are saying

"The ice cream here is delicious, fresh, and creamy."

"I loved their chocolate ice cream with whipped cream and shredded cheese."

"The staff here is so sweet and friendly."

Good to know

1

Nube's Ice Cream & Coffee Shop allows customers to sample unique flavors before purchasing.

2

They offer unique flavors such as blackberry, soursop, and mamey.

3

The shop features a variety of unique South American flavors in addition to common ones.

04
Devil Dawgs on State image 1
Hot dog restaurant

Small, tightly packed hot dog spot with limited seating and a cozy interior. Loud, angsty house music fills the space, creating a lively, club-like atmosphere. Strong food and smoke aromas blend with a communal vibe popular among college students and tourists.

Milkshakes come in large portions and many interesting varieties. They are thick, creamy, and pair well with meals.

Shakes come in rich, creamy varieties like chocolate banana malt and peanut butter chocolate. Flavors such as chocolate strawberry and classic chocolate deliver a smooth, satisfying taste.

People are saying

"I loved the Chicago style hot dog; it was outstanding."

"The onion rings here are so good and perfectly crispy."

"The chocolate shake was rich, thick, and yummy."

Good to know

1

Devil Dawgs on State doesn't accept cash payments; only credit cards and mobile payments are accepted.

2

The seating area is limited, so be prepared for a wait during peak hours.

3

Expect a busy atmosphere, especially around 5PM on Fridays.

05
Van Leeuwen Ice Cream image 1
Ice cream shop

Tiny shop offers constantly rotating unique flavors with great vegan options and free samples. Atmosphere feels warm and inviting despite limited space. Ice cream is creamy and fresh, often praised for authentic taste.

Double chocolate brownie milkshake stands out with rich, intense flavor. Vegan vanilla and pumpkin pie milkshakes offer smooth, melting tastes but some milkshakes can be very liquidy.

Chocolate options include a dark chocolate fudge and a double chocolate brownie milkshake noted for rich flavor. The chocolate shake leans more toward dark chocolate taste and comes at a higher price point.

People are saying

"The ice cream here is so creamy and smooth, especially the specialty flavors."

"I loved the dark chocolate brownie and fudge."

"The Milkshake was solid but a little pricey."

Good to know

1

A single scoop costs over $8, and two scoops are similarly priced to grocery store tubs.

2

The store often runs out of specialty flavors quickly after opening.

3

Vegan options are available for non-dairy diners.

06
Broadway Cafe image 1

Small space with cute tables and a street view creates a cozy vibe. Soft, fantastic music plays, enhancing a relaxed atmosphere. Late hours and peaceful surroundings make it a welcoming spot to unwind.

Milkshakes come in chocolate and strawberry flavors that stand out. They pair well with ice cream and other sweets like cupcakes and cookies.

Hot chocolate comes out not too hot with a slightly savory flavor and balanced sweetness. Chocolate treats include chewy brownies with big chunks, rich mousse pastries, and soft chocolate chip cookies.

People are saying

"I had the best latte I ever tried here."

"I thought the hot chocolate was delicious and not too sweet."

"I really enjoyed the chocolate milkshake here."

Good to know

1

Broadway Cafe opens late, allowing for coffee and cake at night.

2

Expect no menu available for bakery items, limiting choices.

3

Prices are affordable, but some items may not be worth it.

07
Choppers image 1
Fast food restaurant

Old school diner with retro vibe and O.G. Americana decor creates a cozy, nostalgic atmosphere. Classic rock and oldies music play, enhancing the family-friendly setting with indoor and outdoor seating options.

Milkshakes come in large sizes like 32oz and are made fresh. Flavors include fresh banana, strawberry banana, and cinnamon apple pie with apple chunks that add texture.

Chocolate appears in several forms here, including chocolate chip cookies and chocolate peanut butter malts. Chocolate shakes and malts are common dessert choices.

People are saying

"I found the burgers here to be the best in the area."

"I thought the milkshakes here were the best."

"I had an awesome chocolate peanut butter malt."

Good to know

1

Parking is limited, but there is a small lot and street parking nearby.

2

Expect to pay reasonable prices for burgers and meals.

3

The restaurant is family-friendly and suitable for both adults and kids.

08
Superdawg Drive-In image 1
Hot dog stand

Drive-in hot dog stand with car hop service and classic 1950s style creates a nostalgic atmosphere. Eating in cars or at outdoor seating offers a fun family vibe with an authentic old-school Chicago feel. Iconic giant hot dog on the roof marks the well-maintained location.

Real milk shakes and malts come with no skimping on ice cream. Carhops serve filling, amazing milkshakes that stand out.

Chocolate malts stand out with a strong malt flavor that is rare to find. Chocolate milk tastes rich and chocolatey, and they can make it on request.

People are saying

"I thought the hot dogs and cheeseburgers were great."

"This place is a fun, nostalgic drive-in diner."

"I loved their chocolate malt; you could really taste the malt."

Good to know

1

Superdawg Drive-In is a drive-in restaurant where you eat in your car.

2

Parking at Superdawg Drive-In can be challenging.

3

The bathroom is very clean and well-maintained.

09
Ghirardelli Ice Cream & Chocolate Shop image 1

Two-story chocolate shop offers stunning river views and a luxurious yet welcoming atmosphere. The space fills with lively energy and can get noisy and busy, especially with families around. Seating is limited and first-come, first-served, with an outdoor patio providing a more relaxed vibe.

Milkshakes come thick and creamy with real strawberry flavor or rich chocolate lovers taste. They stand out as refreshing and high-quality treats packed with delicious chocolate.

Rich, creamy scoops and handcrafted hot fudge define the chocolate experience here. The World Famous Hot Fudge Sundae and hot chocolate stand out as truly unforgettable treats.

People are saying

"Jameson's service made the chocolate experience feel personal and joyful."

"I loved the nice view overlooking the river and city."

"This milkshake is thick, creamy, and packed with real strawberry flavor."

Good to know

1

There's a special offer on 7/25 for a mini hot fudge sundae at $7.25.

2

Seating is first come, first serve and can be sparse during peak hours.

3

Finding a seat can be nearly impossible during busy times.

10
Drip - Dessert Lounge image 1

Indoor seating shares space with another eatery, creating a lively but sometimes crowded environment. Atmosphere blends vintage ice cream parlor vibes with a street vendor style, offering a chill and welcoming mood. Desserts include churro bites and waffle treats, known for their appealing presentation and variety.

Milkshakes come in unique flavors like Nutella cream and coffee. Portions vary, with some served in small containers but flavors like Oreo and caramel stand out.

Belgian chocolate stands out for its creamy texture and great quality. Dishes often feature chocolate in various forms like dark chocolate-covered strawberries, chocolate ice cream, and Nutella cream milkshakes.

People are saying

"I thought the desserts here were delicious and a must-try."

"You can create your own ice cream treat with so many delicious options."

"I got a milkshake, and it really hit the spot."

Good to know

1

The dessert spot closes late, allowing for late-night treats.

2

Expect to pay around $10 for a small cup of vanilla ice cream.

3

Additional charges apply for toppings like whipped cream.

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