Best Ice Cream Sundaes In Chicago

August 20, 2014 7:00 AM

Photo Credit: Thinkstock

It’s hard to go wrong when you order a sundae. After all, anything that includes ice cream and chocolate syrup has to be good. Yet, there are sundaes that stand out from the crowd, both in terms of size and deliciousness, in no small part because of the variety of toppings. The next time you’re craving a dish of ice cream slathered in chocolate and much, much more, try these five ice cream sundaes.

Margie’s Candies
1960 N. Western Ave.
Chicago, IL 60647
(773) 384-1035

Originally opened in 1921, Margie’s is one of the oldest ice cream shops in town. The parlor — once frequented by The Beatles and Al Capone, just to name a few of its famous patrons — is the place to go big or go home when it comes to desserts. While Margie’s offers regular sundaes of reasonable size, it also offers an enormous array of jumbo sundaes, including a turtle sundae (made with 15 scoops of French vanilla ice cream) and a Swiss milk chocolate sundae, among others. But the biggest and most ambitious sundae of all is The World’s Largest Sundae, of course, made with a whopping half-gallon of ice cream; and every bite is delicious (if you and your friends can finish it all).

Bobtail Ice Cream Company
2951 N. Broadway Ave.
Chicago, IL 60657
(773) 880-7372

The homemade ice cream at Bobtail is just one reason to visit this Lakeview ice cream shop (among its other Chicago-area locations). The creative sundaes are another. Savor traditional sundaes, like the hot brownie sundae, or opt for the more inventive, like the s’more that comes with chocolate ice cream topped with marshmallow, hot fudge and crushed graham crackers. Other sundaes that have to be tasted to be believed include the Nut Bomb and Big O’reo sundaes. If those don’t quite meet your cravings, then you can just create your own and choose all of your favorite toppings.

Annette’s Homemade Italian Ice
924 W. Armitage Ave.
Chicago, IL 60614
(773) 868-9000

Don’t let the Italian ice in the name fool you. This local shop also features a variety of ice creams, from the usual vanilla and chocolate to the more unique, including anniversary cake and raspberry chip cheesecake. For Annette’s most decadent treat of all, go for the hot fudge and brownie sundae with your choice of ice cream with a dollop of whipped cream on top. But when you stroll over to this charming shop, be sure to bring cash, because Annette’s is cash only.

Related:  Best Places to Get Ice Cream

Sugar Shack
630 W. 26th St.
Chicago, IL 60616
(312) 225-6568

Combine some of your favorite splurges when you head to this family-owned Bridgeport ice cream shop. Its famous Funnel Cake Sundae is no regular sundae. Sugar Shack starts with a funnel cake and layers it with vanilla soft serve as well as your choice of one wet topping (like hot chocolate or peanut butter) and one dry topping (everything from chopped pecans to Sour Patch Kids), all for $6.95 for the large and $4.15 for the mini. But it doesn’t stop there; this extravagant sundae also comes with whipped cream and, of course, a cherry on top. For those in favor of a more traditional sundae, Sugar Shack offers many other varieties.

The Office
955 W. Fulton Market
Chicago, IL 60607
(312) 226-0868

For the most exclusive sundae of all, get an invite to the basement of The Aviary, fondly known as The Office. Or gather a group of your closest 15 friends and make a reservation. While the sundae here is of the “make-your-own variety,” as with everything Grant Achatz does, it’s top-notch. Fill your goblet of ice cream with a whole array of delicious toppings. The sundae will cost you $25, but considering the serving size, it’s well worth every penny. So how do you get an invite? While it helps to be a regular at The Aviary. Begging and pleading sometimes helps too.

Related: Best Summertime Desserts in Chicago

Elizabeth SanFilippo is a freelance writer, who enjoys trying new foods from all over the world. But her favorite city for culinary treats will always be Chicago. When not writing about food, she’s scribbling novels, and TV show reviews and recaps. Her work can be found at

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