13 Places for Crazy Milkshakes with WAY More Than a Cherry on Top

Kid-Friendly Restaurants

Have your kiddos been begging for over-the-top crazy milkshakes? These next-level treats have popped up all over Chicagoland at restaurants and ice cream shops!

As if the decadence of a regular milkshake isn’t enough, these extravagant delights pile cookies, donuts, cakes, brownies, candy, and more right on top. Whoa, talk about a sugar rush! Definitely bring a friend or two to share and suddenly, you’ll be named the coolest parent on the block.

Check out our list to find crazy milkshakes near you. And if your favorite over-the-top milkshake place did not make our list, email annie@mykidlist.com or leave it in the comments below.

An over-the-top milkshake piled high with a cupcake, cake slices, and more.

Crazy Milkshakes in the Western Suburbs

Churros and Chocolate

2533 W. Algonquin Road
Algonquin, IL 60102

How does freshly made churros in your shake sound? This little place has all kinds of tasty offerings, including their shamrock churros shakes (on special in March)! They have sundaes and hot chocolate, too.


832 W Randolph Street
Chicago IL, 60607
(312) 967-7000

Does a milkshake made with gelato tickle your fancy? If you venture down to the city, BomboBar is a great stop for these. You’ll also find fancy hot chocolates, bomboloni (donuts without holes), and sandwiches at this spot.

Tizzy’s Ice Cream Treats

737 Plainfield Road
Darien, IL 60561
(630) 887-7486

Family-owned business serving over 30 flavors of ice cream, chocolate-covered frozen bananas, and epic milkshakes piled high with all kinds of treats. They have ice cream cakes as well.

Hey Sugar

507 S. 3rd Street, Suite E
Geneva, IL 60134
(630) 262-8200

Hot chocolate, soft serve, cookies, cupcakes and more. Their cake shakes come in vanilla, chocolate and red velvet varieties, plus seasonal treats (like a mint chocolate shake being served now, in the spring).

Monk’s Burgers and More

88 S La Grange Road
La Grange, IL 60525

Gourmet burgers and mac-and-cheese aren’t the only delicious offerings at this spot in downtown La Grange. They have a variety of hand spun milkshakes ranging from Nutella to salted caramel to Reese’s peanut butter cup.


15112 S Bell Road
Homer Glen, IL 60491

This longtime south Chicagoland favorite serves a wide variety of ice cream treats, including specialty shakes piled high with fun extras. They also have locations in Homer Glen, New Lenox, and Manhattan, as well as one opening soon in Lombard.

Jamos Live

10160 191st Street
Mokena, IL 60448
(708) 981-1400

In addition to a full-service menu including pizzas, pastas, salads, wraps and burgers, their specialty shakes are not to be missed.

JoJo’s Shake Bar

5 W. Jackson Avenue
Naperville, IL 60540
(331) 204-6665

The delicious meals, crazy milkshakes, and treats from their Chicago location are finally available in the western suburbs. Their first two locations are at Chicago’s River North neighborhood and in Water Tower Place.

Sugar Milk Cafe

1250 W Ogden Avenue
Naperville, IL 60563
(630) 857-3194

Sugar Milk shakes are truly over-the-top, with the tallest and most creative add-ons. In addition to these amazing confectionary creations, they also serve tasty breakfast and lunch dishes.

Amerikas Restaurant

734 Lake Street
Oak Park, IL 60301
(708) 613-4254

American cuisine with Latin roots, this place serves up one incredible churro and chocolate milkshake. They serve hot chocolate versions as well if you’re more in the mood for a warm drink.

Crepas Culichi

1101 Lake Street
Oak Park, IL 60301
(708) 637-4998

This new location is loaded with crepes, toasts, and a variety of over-the-top milkshakes stacked with everything from churros, Oreos, cotton candy and more.

Sugar Factory

5445 Park Place
Rosemont, IL 60018
(847) 233-9010

An extensive list of crazy-cool milkshakes, alongside old-fashioned sundaes, hot chocolate, crepes and a dessert fondue. Their whole menu is monster-size and great for sharing.

Crusade’s Burger Bar

209 S Bridge Street
Yorkville, IL 60560
(630) 708-3170

This place always has a “shake of the month” in addition to their regular tantalizing offerings, including burgers. They have a location in Crest Hill, too.

Need a place for the kids to run off some energy after devouring their crazy milkshakes? Don’t miss our list of the Best Indoor Playgrounds and Play Spaces!

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