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Shake Shack
Photograph: Shake Shack Shake Shack

The best milkshakes in Chicago

The best milkshakes in Chicago come in a variety of flavors, from espresso to chocolate cake, at spots around the city

By Amy Cavanaugh and Elizabeth Atkinson

It's not hard to find the best milkshakes in Chicago, considering we're a city with lots of terrific ice cream shops. But Chicago restaurants also turn out some pretty mean milkshakes, from diners to fine dining spots. Here's where we head when we're having a craving.

Best milkshakes in Chicago

Shake Story
Photograph: Wendell Remington

1. Boston Shake at Scooter’s Frozen Custard, $5.45

Restaurants Ice cream parlors Lake View

Scooter's uses frozen custard in its excellent shakes, but order a "Boston shake" and a small chocolate syrup sundae will be added on top. To repeat: That's a sundae on top of a milkshake, and the reason why this is the best shake in town. — Amy Cavanaugh

Dreamsicle (Special Shake) At M Burger
Photograph: Anjali M. PInto

3. Secret Shake at M Burger, $3.49

Restaurants Hamburgers Streeterville

You already know that M Burger has a secret menu (right?). Along with extra hot hurt burgers and cheese fries, there's at least one secret shake at a time. No matter what this is, you want it—sometimes it's coffee, other times it's seasonal, like a mint-chocolate grasshopper for St. Patrick's Day, but it's always thick and delicious. — AC

Shake Story
Photograph: Wendell Remington

6. Miso-Butterscotch Milkshake at Allium, $8

Restaurants Contemporary American Streeterville

Yes, Allium is in the Four Seasons. But if you don't want to shell out for a pricey dinner, grab a spot at the bar and order the shake, which is a perfect blend of salty and sweet. It comes with the added bonus of feeling fancy while you drink it. Wanna get boozy? Add a shot of Fantasia Liqueur ($12).

Photograph: Jason Little

8. Salty Caramel Milkshake from 25 Degrees, $13

Restaurants River North

The California burger spot is perhaps best known for its huge, creamy, boozy shakes, like the salty caramel, well-balanced between vanilla ice cream, butterscotch, Hawaiian red sea salt and a glug of Maker's Mark. It's big enough to share with a friend or serve as dinner on its own, but that's OK—this is one hell of a milkshake. — AC

Photograph: Jaclyn Rivas

10. Oreo Milkshake at Potbelly Sandwich Shop, $3.10

Restaurants Sandwich shops Lincoln Park

Potbelly may be known as a spot to pick up a quick sandwich or soup, but you can also get delicious milkshakes there. Grab the Oreo milkshake, filled to the brim with the delicious cookies, blended with creamy ice cream and topped with two tiny shortbread cookies on the straw. — Elizabeth Atkinson

Chocolate Cake Shake at Portillos

11. Chocolate Cake Shake at Portillo's, $3.25

Restaurants Hot dogs River North

Portillo's blends its very good chocolate cake with ice cream for a shake that's very smooth, with occasional chunks of cake and a layer of frosting that settles at the bottom. It's ridiculous, but hey—you only live once. — AC

Shake Story
Photograph: Wendell Remington

12. Guava Batido at Cafecito, $3.50

Restaurants Cuban Loop

Batidos, fruity and refreshing Cuban milkshakes, are available in rotating flavors at Cafecito. If the guava is available, get it—light and creamy, it's a great match for one of the superb Cuban sandwiches on offer. — AC

Horchata Milkshake at Antique Taco
Photograph: Jaclyn Elizabeth Rivas

13. Horchata Milkshake at Antique Taco, $5

Restaurants Mexican Wicker Park

Antique Taco's milkshake is like a horchata crossed with a fresh banana shake. So the result doesn't taste much like the traditional cinnamon rice milk, but rather a refreshing banana cinnamon shake. It's firmly a dessert, so while it may come out of the kitchen with your tacos, save it until the end. — AC

Find more desserts in Chicago

Photograph: Anjali M. PInto

The best desserts in Chicago


Chicago's top pastry chefs know what people want: ice cream, doughnuts and pie. But while they've mastered—and elevated—traditional desserts, the best spots go above and beyond, with s'more macarons and chamomile creme brulee, to name a few. When you have to end your dinner with the best, here's where to find the best desserts in Chicago.


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