The Best Milkshakes in Chicago

Cold, sweet, and delicious are the three key components to a great milkshake. No matter what the weather is like, milkshakes are a real treat to drink. With so many different flavors, options for toppings, and styles of mixes, finding the finest places to get your milkshake is essential to satisfying your sweet tooth. Known to many, Chicago is one of the ‘best restaurants cities’ in the country, and that includes desserts! Now that summer is just around the corner, finding the best milkshakes in Chicago is a quest many are ready to take, and we have the map just for you!

If you know someone that has a sweet tooth and you would like to get them an extra treat, try GiftYa! GiftYa is a virtual gift card website that has gift cards for a number of online stores, chain & regular restaurants, local businesses, and more! It’s all online, so you don’t have to worry about losing your gift card, plus instead of wondering what the amount you have left on the gift card is, GiftYa tracks it for you! So you know exactly how much to spend, and how much to enjoy with your GiftYa gift card.

You can gift your own GiftYa gift card right here! 

The Chicago Diner

Serving the very best award winning vegan milkshakes!

Scooped by hand and blended just right to make the perfect shake! Image courtesy of The Chicago Diner Instagram page.

2333 N Milwaukee Ave | Chicago | veggiediner.com 

Since opening in 1983, The Chicago Diner has always been “going against the grain” with serving an all vegetarian menu, this establishment has been setting the bar when it comes to great food and even greater habits. Today more than ever, people are trying to find delicious foods that fit their dietary wants/needs, and The Chicago Diner has that in spades. Along with their classic vegetarian menu, they now also offer gluten free, dairy free, and vegan dishes!

Milkshakes are a favorite from this diner, and there are options for every dietary restriction, which makes all customers feel included, so they have no worries enjoying this cold drink!

Milkshakes have their own section on their dessert menu, flavors include, Pumpkin Pie (GF), Chocolate Chip Cookie Dough, Chocolate Peanut Butter (GF), Cookie Dough Peanut Butter, Mint Chocolate Chip (GF), Chocolate (GF), Banana (GF), Vanilla (GF), and Strawberry (GF)! 

“I'm trying to be more plant based and this restaurant always has the best vegan food. You wouldn't even know you weren't eating meat if they didn't tell you. I highly recommend their amazing quality food. They have two locations and this is the larger one :)” -Yelp Review

You can Purchase a GiftYa Gift Card to The Chicago Diner here!

JoJo’s Shake Bar

Whether it’s a classic shake or an over the top blend, JoJo's the place to be!

Shake with desserts for toppings? Count us in! Image courtesy of the JoJo’s Shake Bar Instagram page.

23 W Hubbard St | Chicago | jojosshakebar.com 

“JoJo’s Shake Bar is the next generation restaurant and bar.” It has unique and whimsical design that adds to their diner-esque foods and creative milkshakes. Their menu is the definition of big and extravagant, JoJo’s Shake Bar has classic shakes and truly incredible mixes that definitely need a further look into:

• The basic shake menu has vanilla, blueberry, chocolate, caramel, strawberry, and banana.
• Their current “Biggie Shakes” menu, (an example of how they are constructed can be found on their website or their instagram, (see above)), are some of the best milkshakes in Chicago, here are just some of them: 
• Wonder Years, a blueberry shake with candy marshmallow, gummy candy ribbon, and cotton candy, the Gold Digger, a caramel toffee shake, with toffee dodo and pretzel, gold star marshmallow, and white chocolate macadamia nut cookie, and then the Girl Scout, an andes mint chocolate shake, toasted marshmallow, chocolate pretzel, chocolate s’more, and double chocolate chip cookie!

JoJo’s Shake Bar is bringing the meaning of having a sweet tooth to a whole new level!

“JoJo's was a huge hit with our family on our recent visit to Chicago, so much so that we had to eat there twice. Cute decor and vibe, and really excellent service. Everyone loved their food - the grilled cheese, buffalo chicken wrap, fries, salads, and a decadent chocolate shake were all greatly enjoyed.” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

Scooter's Frozen Custard

A spot built for the lovers of all things frozen!

Chocolate, chocolate, and more chocolate = perfect. Image courtesy of the Scooter’s Frozen Custard Instagram page.

1658 W Belmont Ave | Chicago | scootersfrozencustard.com 

Mardi and Denny Moore first opened Scooter’s Frozen Custard in 2003, and ever since that day, it’s been a grand success, with a line out the door on the very first day! Mardi and Denny, both Chicago natives, didn’t think they were going to be able to run a successful shop, but they were wrong, as Scooter’s Frozen Custard has become a Chicago favorite. With their main goal of wanting to build a stronger community by knowing their neighbors, this top shop’s reputation goes well in hand with how great their frozen treats are!

Now their menu is huge, with a number of concretes, sundaes, cones/cups, shakes, malts, floats, Italian ice, pints, quarts, pies, and more, your craving for something sweet will truly be complete. 

Some of their popular milkshake flavors include their award winning Boston Shake, a milkshake of any flavor with a chocolate sundae plopped on top and Scooter’s Fruitter, a refreshing milkshake made with pineapple juice and two fruit flavors!

“I LOVE SCOOTERS. Delicious, fast, fun. Their custard is worth craving. No matter how many people are in line, they still manage to serve quickly. Huge fan will come back often.” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

The Freeze

Since 1950, this shop has been the OG of soft serve!

2815 W Armitage Ave | Chicago | tastee-freez.com 

Don’t let the size fool you, The Freeze, formally known as Tastee Freez, has been serving the best type of sweets since 1950. This popular spot has some of the best shakes, sundaes, burgers, and floats in the city!

Thick and creamy milkshakes are made with that delicious soft serve. Coming in a variety of flavors like vanilla, chocolate, strawberry, and more seasonal favorites are all available at this Windy City favorite!

“This place is so charming. Very old school feeling. The soft serve was perfect and the root beer float tastes like root beer made from a syrup the old fashioned way. They had lots of other food and treats on the menu too!” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

DMK Burger Bar

An award winning restaurant putting its own flare on shakes!

Handmade shakes to brighten anyone’s day! Image courtesy of the DMK Burger Bar Instagram page.

2954 N Sheffield Ave | Chicago | dmkburgerbar.com 

Restauranter David Morton and Chef Michael Kornick opened the first DMK Burger Bar in 2009, proudly serving 100% grass-fed beef patties, bison, and all natural turkey burgers; this burger bar has been awarded and nominated for so many things. Whether you want a meal or just stop by for a shake, this restaurant has got it all!

House made shakes are available in vanilla, chocolate, toasted marshmallow, peanut butter, and their “shake of the month”, which is DMK’s special unique flavor that is made for every month to keep things interesting. (Plus if you’re in the mood for a kick, you can make each of these shakes alcoholic)! DMK Burger Bar has plenty to offer with their menu and atmosphere!

“Love these burgers and fries and so do all my friends!! Can't go wrong with anything at DMK! The Mac and cheese was tasty too! The Milkshakes are boss! Always have some tasty beers in stock also! Never had a bad burger or fries!” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

Portillo’s

An American fast casual restaurant chain taking the Chicago area by storm!

Pair your shake with a good meal! Image courtesy of the Portillo’s Hot Dogs Instagram page.

100 W Ontario | Chicago | portillos.com 

Back in 1963, Dick Portillo invested 1,100$ into the very first Portillo’s, years later every Chicagoan knows about this famous hot dog chain. Portillo’s is self described as a Chicago icon, and from their many many locations around the Illinois area, it seems to be that way! This classic diner specializes in Chicago-style hotdogs, cheese fries, Italian beef sandwiches, and of course milkshakes!

Portillo’s has “flavor of the month/season” where they do a special milkshake mix of either the current holiday or season. In the past they have done a Candy Cane milkshake for Christmas time, Chocolate Covered Strawberry Shake for Valentine’s Day, and Mint Chocolate Shake for St. Patrick’s Day! 

Right now for spring they have their Lemon Cake and Strawberry Lemon Cake Shakes! Always on the menu however is Portillo’s famous Chocolate Cake Shake, Vanilla, Chocolate, and Strawberry shakes!

“One of my new favorite must have places to eat at in Chicago! The options are endless, making it easy for everyone to find something to enjoy. The Italian sub was delicious and so fresh! It pairs nicely with their cheese fries and chocolate shake! Make sure to try out the chocolate cake for dessert!” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

M Burger

Quick service, good quality, and fast food to bring the best milkshakes in Chicago!

Milkshakes in every flavor are great milkshakes! Image courtesy of the M Burger Instagram page.

161 E Huron St | Chicago | mburgerchicago.com 

Proudly serving the Chicagoland area, M Burger has three locations in Illinois that have their mission statement right in center, “creating memories one handmade burger at a time.” They take pride in their food, products, and partnerships, and they have done so since the very beginning. Now you’re here for the milkshakes, and M Burger uses nothing but midwest dairy for their shakes and other delicious desserts!

Whether you want a shake or malt, you have flavor options like vanilla, chocolate, hand-made hot fudge, caramel, and 100% strawberry! M Burger also does “Shake of the Month”, and currently for May they have their Blueberry Pie Shake, which is full of fresh blueberries, midwest vanilla ice cream, and graham cracker crumble! Make sure to check back each month to see what M Burger’s new shake of the month is!

“Out of town ... stopped to get a burger. They were delicious. I got a vegetarian burger and my son ordered a regular . The fries were my favorite and the shake was delicious . Would totally eat here again. Super cool customer service too !!!” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

Irazu Costa Rican Restaurant & Catering

Serving traditional Costa Rican food & shakes in a vegetarian-friendly menu!

Plenty of stylishly tasty foods/drinks to enjoy including some of the best milkshakes in Chicago! Image courtesy of the Irazu Costa Rican Restaurant Instagram page.

1865 N Milwaukee Ave | Chicago | irazuchicago.com 

The Cerdas-Salazar family has had a dream, and that came true back in 1990 when they first opened up their Costa Rican Restaurant Irazu. They have felt fortunate to have the unique opportunity to share their traditional home cooked foods to the people of Chicago, and from the reviews, they have been succeeding!

Now Irazu has a ton of food on their menu, but we’re here to talk about milkshakes! They have a good array of flavors and some you may have not tried before, from oatmeal, banana, vanilla, chocolate, mango, passion fruit, lime, coconut, strawberry, and Guanabana! You can choose milk, soy milk, water, or horchata for your base, plus have a double or single! So many flavors and options for your milkshake needs at Irazu!

“Second time trying Irazu, this time went in on a Saturday, we were seated in a few minutes. Food was ready in less than 15 minutes. Everything was delicious. My favorite was the plantains and the horchata shake with oatmeal base . But next time will get it after I'm done eating, it is pretty filling.

Can't wait to go again” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

Superdawg Drive-In

Bringing the old drive-through style to Chicago delivering food & drinks!

Get a hotdog with the best milkshake in Chicago! Image courtesy of the Superdawg Drive-in Instagram page.

6363 N. Milwaukee Avenue | Chicago |  superdawg.com 

In May 1948, Flaurie and Maurie opened a hot dawg stand in Chicago to help work their way through college, through the love of each customer and the great environment set, Superdawg has been serving the very best! Their goal is to make sure every visit is one to leave you wanting to come back and bring someone you care about with you!

At Superdawg, they have the aptly named Supermalts and Supershakes, which is a full pint of smooth creamy refreshment so thick they put the straws through them to show that you can’t pull them back out! (Though if you prefer a more thin milkshake, they can make them for you exactly how you like)! On the flavor side, Superdawg has double rich chocolate, real fruit strawberry & pineapple, and mellow vanilla!

“Best dogs in Chicago, never a dull moment! Their burgers are so amazing too! Super cheesy is sooo good! The strawberry malt drink is life changing  it's our family tradition to come here before every flight we take, we have to stop by here and eat in the amazing Superdawg!!” -Yelp Review

Although this restaurant doesn’t have a GiftYa gift card opportunity yet, check back soon, as new places are being added to the GiftYa website frequently!

So now you know the best milkshakes in Chicago! You can be in the mood for a meal to enjoy with your shake or have the shake on its own, it’s still going to be a grand ol’ experience having some sweet sugary goodness in the Windy City!