Shake It Up: 9 Best Milkshakes in Chicago

Summer is heating up in Chicago, and soon we’ll be desperate for ways to keep cool. Our advice: Keep calm and sh-sh-shake off that heavy mid-summer humidity with the best of Chicago’s creamy, cool desserts — milkshakes! Sip ‘em neatly through a straw or scoop ‘em messily with an oversized spoon; go chocolate-y sweet or fruity and refreshing.

Here’s our list of the nine best milkshakes in Chicago and the North Shore (in no particular order). Disagree? Have something to add? Let us know in the comments below.

Devil Dawgs

767 S. State St., Chicago, 312-583-9100; 2147 N. Sheffield Ave., Chicago, 773-281-4300

Devil Dawgs milkshake

What You Want: Salted Caramel Pretzel Shake

Creaminess Factor: 9

Thickness: 8

Broken salty pretzel rods cut right through the sweetness of thick vanilla ice cream and warm caramel in this shake to create a serious salty-sweet sensation for your taste buds.

Devil Dawgs owner and chef Alan Katz says they offer customers huge straws in an array of colors to ensure patrons taste the full flavor of their shakes in just one gulp. Katz also says they use 10-percent butterfat ice cream—we’re talkin’ the real deal—in all of their 25 shake flavors. From Hot Fudge Marshmallow to Chiquita Fresh Banana, customers have a variety of choices to pair with any of Devil Dawgs’ famous Chicago-style hot dogs. Did we mention there are 15 kinds of those?

Located across the street from Jones Prep School and next door to Columbia College, their South Loop location attracts lines of teens and twenty-somethings starting around 3:15 p.m., so get in line now!

Café Buongiorno

586 Chestnut St., Winnetka, 847-784-8899

Café Buongiorno milkshakes

What You Want: Espresso Shake

Creaminess Factor: 8

Thickness: 5

Wake up your taste buds with this creamy coffee milkshake made with rich vanilla ice cream and an actual shot of espresso. Owner Mary Jo Vlahos says she didn’t want the concentrated coffee flavor that she knows some ice cream shops use. This shake is an adult favorite of her customers and ours.

What Your Kids Want: Oreo Shake

For the children, Vlahos says the Oreo flavor is the go-to. They first combine Oreos and milk and then blend the sweet mixture into ice cream to create thick, chocolatey cookie goodness. We also recommend any of their fresh fruit milkshake flavors, which include strawberry, pineapple and even blueberry!

Superdawg 

6363 N. Milwaukee Avenue, Chicago. 773-763-0660

333 S. Milwaukee Ave., Wheeling, 847-459-1900

Superdawg milkshakes

What You Want: Chocolate Shake

Creaminess Factor: 6

Thickness: 6

When you’re looking for the ultimate chocolate shake, you’ve got to get to Superdawg. No whipped cream necessary, this shake sits right in the middle of our creamy and thickness ranking—as Goldilocks might say, it’s just right.

A Chicago staple, Superdawg has been at its location at the intersection of Milwaukee, Nagle and Devon since May 1948. Operations Manager Don Drucker, who married into the family business, says the establishment is most famous for its chocolate malts—but we promise that any of the shakes (chocolate, strawberry, vanilla) will leave you “super” satisfied.

25 Degrees

736 N. Clark St., Chicago, 312-943-9700

25 Degrees milkshake

What You Want: Bananas Foster Shake (Adults only!)

Creaminess Factor: 10

Thickness: 7

This one we would have to rank among the Seven Deadly Sins of Milkshakes. Homemade Butterscotch Sauce, half of a banana, an ounce each of Meyers and Sailor Jerry rums and an entire pint of Haagen-Dazs ice cream blend harmoniously to create a dessert that’s both warm and spicy, and also cool and sweet.

25 Degrees, known for its sophisticated twist on the traditional burger bar, has been at its River North location on North Clark for about four years. Toppings like arugula, pesto and fontina cheese sprinkle the toppings section of the burger menu. With dark leather booths, dim chandelier lighting and red wallpaper, this burger bar’s ambiance will take your milkshake experience to another level.

R.J. Grunts

2056 N. Lincoln Park West, Chicago, 773-929-5363

R.J. Grunts milkshake

What You Want: Peanut Butter Oreo Shake

Creamy Factor: 6

Thickness: 7

If “The Parent Trap”’s Halley and Annie could dream up a milkshake, we bet you it would be this one. Smooth like Skippy, this oh-so-delicious shake has peanut butter and premium vanilla ice cream blended with a heaping amount of Oreo pieces, and then topped with whipped cream, and even more Oreo pieces.

R.J. Grunts strawberry milkshake

Bonus! Chocolate-Covered Strawberry Shake (Adults only!)

This spiked shake, concocted by R.J. Grunt’s manager Ava Fisher, combines vanilla ice cream, fresh strawberries, vanilla vodka and Godiva Chocolate Liqueur for a sinfully sweet treat. It’s the perfect dessert for a summer date night or an appetizer for a girls’ night on the town. Fisher says one of the servers’ favorite things to do is come up with different milkshake combinations. Customers are also welcome to come up with their own combinations for regular and adult milkshakes alike.

Located in Lincoln Park, R.J. Grunts is Lettuce Entertain You’s very first establishment. “R” stands for Rich Melman and “J” for Jerry Orzoff, his late business partner. R.J. Grunts opened in 1971 and struggled for the first several months but business turned around quickly and now it is considered a Lincoln Park staple. The  restaurant’s claim to fame: the first salad bar, but don’t fret if you feel salad doesn’t mix well with milkshakes; they also serve burgers, wings and fries.

Dairy Star

3472 W. Devon Ave., Lincolnwood, 847-679-3472

Dairy Star

What You Want: Marshmallow or Root Beer Shake

Creamy Factor: 4

Thickness: 5

Ready to return to the summers of your childhood? Head over to Dairy Star in Lincolnwood and wait in line at the ice cream stand that has been serving rainbow-sprinkled soft-serve cones for more than 28 years.

Dairy Star milkshake

Both Dairy Star’s marshmallow and root beer shakes make our favorites list. Their soft-serve ice cream delivers shakes fluffy and smooth though the straw. These shakes won’t weigh you down, so we recommend them after a long day at the beach or a hot afternoon at the baseball diamond.

Oberweis

Multiple locations

Oberweis milkshake

What You Want: Chocolate Marshmallow

Creaminess Factor: 10+

Thickness: 8

In the land of milkshakes, we deem these the richest of them all. Under a cloud of thick whipped cream and a Pirouette chocolate cookie, you’ll find their minimum 18-percent butterfat ice cream. Chocolate Marshmallow is our favorite flavor but runners-up include Birthday Cake, Chocolate Peanut Butter and Brownie Fudge Twirl.

Oberweis has been making and delivering milk since 1927 when they started their home delivery service. It has been perfecting ice cream since they opened their first dairy store in 1951. They have locations all across the North Shore including Park Ridge, Lincolnwood and Glenview, with a location in Lincoln Park as well!

Susie’s Drive-In

4126 W. Montrose Ave., Chicago, 773-283-6544

Susie's Drive-In milkshake

What You Want: Banana Split Shake

Creaminess Factor: 4

Thickness: 6

A banana/chocolate ice cream called “Baboon” (a flavor created by owner Stacy Ninos‘s father) serves as this shake’s base, while classic sundae toppings of fresh strawberries, pineapple, whipped cream, nuts and a cherry pile up to fill one of Susie’s styrofoam cups with a sip-able, refreshingly sweet shake.

Susie’s has been serving customers for nearly 42 years, and Ninos says they see their fair share of regulars. The drive-thru stand features more than 60 flavors of shakes with everything from classics to adult milkshakes like Piña Colada to fun seasonal flavors like Witches Brew, which actually bubbles with foam!

What on the menu pairs best with your shake? “Anything with beef,” Ninos says. And with options like beefsteak fries, meatball cheese fries and classic beef subs, you’re sure to find at least one ideal savory selection.

Edzo’s

1571 Sherman Ave., Evanston, 847-864-3396

Edzo's milkshake

What You Want: Nutella

Creaminess Factor: 8

Thickness: 8

Nutella fanatics, have we got the shake for you! The creamy chocolate/hazelnut spread everyone loves to spoon directly into their mouth comes in milkshake form at Edzo’s Burger Shop in Evanston. “The theme that runs through Edzo’s is basic, no-frills diner/hot dog stand feel meets high-end gourmet approach/ingredients,” says chef and owner Eddie Lakin. So the secret to the shake’s thickness is not the non-premium Kemp’s vanilla ice cream they use but rather their old-fashioned slow-blending spindle machines, which keep air out, while twirling the Nutella and vanilla ice cream into a marvelous matrimony of smooth, rich flavor.

If Nutella isn’t your jam, we recommend you try some of their other famous and unique flavors like Spicy Mexican Chocolate, Salted Caramel, Toasted Almond, Fluffernutter, The Elvis (peanut butter, banana and chocolate) or Speculoos Cookie. Lakin says the shop is known for their seasonal special shakes. Around the holidays, you’ll discover Egg Nog, Candy Cane and Gingerbread shakes; enjoy a Pumpkin Pie shake in the fall; and seasonal fruits like Fresh Michigan Strawberry and Key Lime Pie are available this summer.