Hey there, Chicago food lovers!
We’re the Ben Lalez Team, and after helping over a thousand families find their perfect Chicago homes over the last decade, we’ve learned it’s not all about real estate. The neighborhoods people actually want to live in aren’t just about good schools and quick commutes. They’re about having places worth going to when something good happens in your life.
And sometimes, that means a milkshake with an entire slice of cake on top.
Chicago takes desserts seriously. Not the fancy, delicate kind. The kind that makes you laugh out loud when they bring it to your table. These places will have your kids talking about it for months and give you stories to tell at dinner parties.
The Ones Making Everyone’s Phone Come Out
JoJo’s ShakeBAR basically said, “What if we put everything on a milkshake?” and then actually did it. The Biggie Shakes come with whole slices of cake, full-size cookies, candy bars… stuff that has no business being on a drink but somehow works. You can find them in two places in Chicago.
The seasonal stuff gets truly wild. Fall brings the Pumpkin Patch shake, made of pumpkin cake, whipped cream, candy corn, and orange everything. Winter means the Peppermint shake that looks like Christmas threw up in the best possible way. Year-round, you can get the Birthday Cake Biggie or the S’mores version with actual graham crackers and marshmallows stuck to the glass.
Sugar Factory at 112 W Hubbard St in River North does their “King Kong” sundae with dry ice smoke and sparklers that they light at your table. This isn’t food, it’s a show! The sundae is huge, meant for sharing, loaded with enough sugar to power a small city. You’ll feel silly ordering it, but that’s the point. When you close on your dream home and want the whole restaurant to notice, this is where you celebrate.
The Chicago Originals Who Started This Madness
Margie’s Candies opened in 1921 and has been doing ridiculous portions ever since. They serve sundaes in those silver boat things, but the portions are what your great-grandmother would call “appropriate for a family of eight.”
The hot fudge flows like a river. The whipped cream gets piled on like they’re building something. Their Turtle Sundae has vanilla ice cream, hot fudge, caramel, whipped cream, nuts, and a cherry, but when they make it, each component becomes its own layer. Two people can share one easily. The building feels like you walked into 1950, which makes eating something this big feel totally normal.
But if you want something super crazy, check out their World’s Largest Terrapin. You’ll need help eating this one.
Rainbow Cone takes five flavors and stacks them on one cone, then slices them like you’re cutting a loaf of bread. Chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet.
They’ve been doing this since 1926. The slicing gives you all five flavors in every bite instead of working through layers. Palmer House flavor is theirs exclusively and is named after the hotel. You can’t get it anywhere else. Watching them slice your cone is part of why you go.
Portillo’s blends an entire slice of chocolate cake into a milkshake. The cake is moist and rich, and the shake comes out thick enough that you might need a spoon. The chocolate cake itself would be a solid dessert on its own, but they decided to make it drinkable because that’s just how we do things here.
The New Places Pushing Things Further
BomboBar brings Italian gelato but makes it Chicago-sized. Gelato shakes with multiple flavors and mix-ins, bomboloni stuffed with gelato or Nutella. Winter brings hot chocolates loaded with marshmallows and whipped cream, and enough chocolate to make you question your decisions while you’re making them.
KURIMU does fish-shaped cones filled with soft serve in flavors like Purple Yam with Oreo, Thai Iced Tea, and Sweet Corn. The cones get made fresh and come out warm, so you get this contrast between the warm, slightly sweet cone and the cold ice cream.
They rotate seasonal flavors, like Ube in spring, and Black Sesame in fall. The combinations sound weird, but taste right. Everything looks ready for Instagram, but more importantly, the flavors actually work together instead of being weird just to be different.
Xurro figured out churros needed ice cream in the middle. Two crispy churro wheels, split open, and ice cream smashed between them. It’s messy as hell and worth every sticky finger. They also do funnel cake sundaes – whole funnel cake, ice cream on top, whipped cream, and whatever sauce you can handle. It’s county fair food in the middle of the city.
When You Want To Show Off
RPM Steak has chocolate cake with a 14-karat gold leaf on top. It’s completely unnecessary, and totally memorable. The cake would be impressive without the gold, but the gold makes it into an event. This is anniversary dinner territory, when you want dessert to be something you’ll still talk about next year.
Gibsons Italia lights their Spumoni Baked Alaska on fire at your table. It’s spumoni gelato, cake, and meringue. The server brings it out, pours liqueur on it, and lights it up. Every table in the restaurant turns to look. Perfect for celebrating something big and wanting everyone to know about it.
The Everyday Champions
Small Cheval does boozy milkshakes for adults, and Chocolate Cake Concrete for everyone else. The concrete comes thick with actual cake pieces and fudge sauce. It’s dense enough that you need a spoon, and rich enough that sharing makes sense. The boozy shakes use good spirits that complement the flavors instead of just adding alcohol for the sake of it.
Firecakes Donuts takes a warm glazed donut, splits it, and packs it with ice cream. It’s a simple concept that’s executed right. It’s the perfect combination of warm and cold, sweet and slightly salty, and soft and creamy. Their raised donuts are light enough that they don’t compete with the ice cream.
Legend Tasty House makes rolled ice cream while you watch. They pour the liquid base onto a frozen plate, add mix-ins, and scrape it into rolls. Then they put it in a bubble waffle that comes warm and crispy with those bubbles that hold pockets of ice cream. Half the fun is watching them make it, but the result tastes as good as it looks.
Eiffel Waffle specializes in bubble waffle cones loaded with cereals, cookies, and sauces. Their “Cookie Monster” has blue soft serve with actual cookies and cookie crumbs. The bubble waffles get made fresh and shaped into cones while warm, so you get a crispy shell that holds whatever combination you put together.
Worth The Extra Trip
Ghirardelli at the Wrigley Building on Michigan Avenue serves their Earthquake sundae. It’s multiple scoops of ice cream, hot fudge, whipped cream, nuts, and enough cherries to stock a bar. It’s a tourist spot for sure, but the portions are real and the location works if you’re already downtown.
The Peninsula Chicago sometimes runs a seasonal Chocolate Bar with all-you-can-sample chocolate and action stations where they make liquid nitrogen ice cream and hot chocolate bombs in front of you. It’s not permanent, so call ahead. But when it’s running, the spectacle is worth seeing.
The Final Scoop
One thing we know is that Chicago doesn’t do subtle. Our pizza is thick, our hot dogs have rules, and our desserts take up half the table. We like things that make a statement, and that’s just part of being proud.
We hope this gives you some new places to try. Just don’t attempt them all in one weekend. We learned that lesson the hard way.
And if you’re looking for more articles on all things Chicago, check back here weekly. We’re proud of being one of the top real estate teams in Chicago, but we’re just as passionate about sharing everything we love about living here!
