The Best Milkshakes in Chicago

June 18, 2020
jason wolfe

6 spots for milkshakes that are sure to impress anyone’s sweet tooth

Milkshakes are a great treat no matter what the weather is like. They are sweet, heavy, and delicious. With so many different flavors and options for topics, there is so much room to explore different places that have milkshakes. Chicago has a booming restaurant scene which includes desserts. With the weather being warm now, head out to get some milkshakes after work or school!

If you or someone close to you has a sweet tooth, make sure to get them a GiftYa electronic gift card to any of these places listed below! It is super easy to purchase and also easy to use! Every once in a while, someone else paying for your dessert is a nice treat.

Public House

400 N State Street

River North |

Serving up the sweetest milkshakes in Chicago

Milkshakes at Public House come with a massive piece of cake on the top! Image courtesy of Public House.

Public House has many different faces to it. During the week it serves as a dive bar that serves classic bar food such as grilled cheese and nachos while also having over 100 beers available. On the weekends, there is brunch in the morning and at night it becomes a fun place to dance with a live DJ. An item on the menu that is an absolute staple are their milkshakes. 

These Chicago milkshakes are a must try! Currently there are two options on the menu at Public House. They are the Chocolate Porter and Vanilla Stout. In the Chocolate Porter there is chocolate ice cream, chocolate candies on the side and then a huge piece of chocolate cake that sits on the top. The Vanilla Stout consists of casper white stout, vanilla ice cream, and buttercream cake on top. There is also an option to add a shot into both of the milkshakes. If those options are not up your alley, then there are seasonal options, just ask the server!

Buy a GiftYa to Public House >

“We finished up with some gourmet boozy shakes, a Public House staple. These shakes come out so beautifully that you almost wish you could frame it and never touch it again...until you realize it's a milkshake...with alcohol...topped with a piece of cake...and then your desire to frame it is taken over by your ravenous approach to consume every crumb.”- Yelp Review 

The Chicago Diner

2333 N Milwaukee Avenue 

Logan Square |

Don’t let dietary restrictions stop you from these milkshakes

These vegan milkshakes come in many different flavors. Image courtesy of Eater Chicago.

Today, more than ever, people need to request from many different dietary menus, such as gluten free, dairy free, and vegan for a few examples. This makes going out tough for some. Since opening its doors in 1983, The Chicago diner has been vegetarian and now also serves vegan and gluten free food options as well. Milkshakes are a favorite from this diner, and there are options regardless of your dietary restrictions. Customers who do not require dietary restrictions also enjoy the abundance of diner food options!

These award-winning milkshakes come in flavors such as: cookie dough peanut butter, chocolate chip cookie dough, and chocolate covered pretzel. For gluten free options, there are: chocolate peanut butter, banana, chocolate, vanilla, and strawberry. 

Buy a GiftYa to The Chicago Diner >

“I've been here a few times and haven't been disappointed. You MUST get a milkshake--the best vegan shake I've had, and indistinguishable from a non-vegan milkshake.”- Yelp Review

JoJo’s Shake Bar

23 W Hubbard Street

River North |

A combination of classic and over the top milkshakes

Massive Chicago milkshakes that will leave customers full and satisfied. Image courtesy of Jojo's Shake Bar.

Jojo Shake Bar is combining classic milkshake flavors but adding their own flare to them with over the top milkshake sizes and flavors. Their extravagant menu has any milkshake imaginable. From small and basic ones to crazy named, over the top ones.
Their $14 “biggie shakes” are a Chicago favorite. Just from the names, customers can tell that they are in for a great surprise. Currently the six options for biggie shakes are: The Wonder Years, Gold Digger, Rocky IV, Three’s Company, Girl Scout, and Chocolate Nirvana. Just to name a few ingredients in those options are marshmallows, chocolate cookies, and chocolate pretzels.
For a more standard milkshake, there are chocolate, vanilla, strawberry, and banana flavors. Each one can be filled with a heath bar, oreos, M&M’s, and Reese’s Pieces. 

“We got one milkshake to share. It was one of their specials that evening. I don't remember the name of the milkshake, but it was delicious. The milkshake was delicious, and I'd come back for another one.” - Yelp Review

Shake Shack

Multiple locations

Multiple addresses |

Everybody loves a burger and a shake
This is a huge milkshake that is available for purchase! Image courtesy of Shake Shack.

Shake Shack is a well-known restaurant chain that has many locations across the United States. It is famously known for their simple burgers and milkshakes. In the city of Chicago, there are multiple locations for people to enjoy.

Their milkshakes are so well-known due to their simplicity and how good they taste. The flavors to choose from are as follows: vanilla, chocolate, salted caramel, black & white, strawberry, cookies & cream, and coffee fair. Although these flavors are pretty standard, the simple taste of them all have kept customers satisfied and coming back. 

Buy a GiftYa to Shake Shack >

“We tried three shakes salted Caramel peanut butter and strawberry all were flavorful. The strawberry tasted like it was made with real strawberries.”- Trip Advisor Review

Scooter’s Frozen Custard

1658 W Belmont Avenue

West Lake View |

Voted the best milkshake in Chicago

Scooter's Frozen Custard - Chicago, IL | Groupon
An award winning milkshake outside the best milkshake restaurant in Chicago. Image courtesy of Glassdoor.

Since its opening in 2003, Scooter’s has been very successful. On their very first night in business, the line was out the door and it has only gone up from there. Owners, Mardi and Denny Moore are both Chicago natives who never thought they would be running a successful shop coming from sales and telecommunications backgrounds, but they were very wrong. Their ultimate goal in running this shop is to build a stronger community getting to know their neighbors.

Their thick Chicago milkshakes won them the best milkshake in the city. A reason Scooter’s won best milkshake is because they make any milkshake flavor customers ask for and even add chocolate syrup on top. For those who are lactose intolerant, there is an option called “Scooter’s Fruiters” which replaces the milk of a milkshake with pineapple juice and then the customers’ choice of two fruit flavors.

Tastee Freez

Logan Square 

2815 W Armitage Avenue |

A classic ice cream shop

A tiny space filled with great food for family and friends.  Only a few seats are available so going in the summer when it's nicer is a great idea.

Image courtesy of Time Out.

Serving the best type of sweets since 1950, The Freeze is a Chicago favorite.  Do not let the size of it fool you. It may be small, but it has some of the best shakes, sundaes, burgers, and floats in the city!  The flavors range from snickerdoodle, banana, to even pecan.  Even though The Freeze does not only serve milkshakes, it is a place locals and visitors should try for ice cream, burgers and milkshakes.  

Buy a GiftYa to Tastee Freez >

“I love the Freeze! The staff here is so friendly and kind, and the ice cream is delicious. If you're a fan of soft serve, this is the spot in Chicago to go. It feels like one of those throw back, classic neighborhood spots that make you feel nostalgic. I love the dipped cones and the freeze, which reminds me of a blizzard.”- Yelp Review


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