Three Must-Try Chicago Desserts

Introduction

The older we get, the more we realize that life never really flows as planned. Seven years in NYC, and one would think that we have traversed most of the U.S. and/or the Americas and then some. Sadly, that’s not the case. Two and a half year disappeared due to Covid, and the rest…we have no idea. Altough Chicago was only about 2 hours by plane from NYC, we never managed to visit this city either. *Sob* On a recent trip from the other side of the world, Chicago sadly reminded us more so of why we still miss NYC’s incomparable buzz and hustle so so much, even almost two years since leaving it. To blunt that pain, we traipsed through the city to find its three most touristy, iconic, must-eat desserts. Are they worth the long-standing fame? Have you tried them?


Garrett Popcorn

  • ☑ Dessert destination: Garrett Popcorn, 4 E Madison, and other locations. 
  • ☑ Budget: $.
  • ☑ Short and sweet story: What’s the best thing about going to the movies? We would say, not necessarily the movie itself, which can be hit or miss, but rather, that large paper bag of freshly toasted, ultra buttery popcorn that was always the perfect reliable accompaniment to any movie outing. We never thought we would feature popcorn on this dessert blog, but there’s a first for everything, eh? 😛  Before we went to Chicago, we were told to not miss Garrett Popcorn, and we admit that we were quite dismissive of the idea that it would be worth the visit. Nonetheless, we tried it while in Chicago, and we are glad we did. In typical over-the-top-American fashion, Garrett Popcorn curiously throws cheese popcorn and caramel popcorn and butter popcorn into a single bag, shake it up, and the result is a very addictive mix of sweet, salty and savoury. Should have got an XL bag, instead of mini.  😛

Rainbow Ice Cream Cone

  • ☑ Dessert destination: Rainbow Cone, 600 East Grand Avenue, and other locations. 
  • ☑ Budget: $.
  • ☑ Short and sweet story: In NYC, the most touristy ice cream has to be from the Brooklyn Ice Cream Factory. In Chicago, the equivalent is the Rainbow Cone. In operation since the 1920s, Chicago’s Rainbow Cone comprises five ice cream flavours slapped — rather than scooped — on top of each other. Chocolate, strawberry, pistachio, orange sherbet, and “Palmer House” cherry,  it’s a more carnival-esque confection, rather than proper ice cream. The end product is soo incredibly sweet, and becomes such a drippy mess so quickly, that we managed to lick it for less than five minutes before the rest had to be tossed. Fleeting moments of fun, indeed. If you are an ice cream connoisseur, this is not for you, but if you don’t mind a significant dose of old-school Americana, you can certainly consider it. 

Stan’s Doughnuts

  • ☑ Dessert destination: Stan’s Doughnuts, 181 Michigan Avenue, and other locations.
  • ☑ Budget: $.
  • ☑ Short and sweet storyArguably, the most “American” of desserts is the doughnut. We have eaten all of the best doughnuts in NYC, tracked the many variations of the mochi doughnut trend, hunted down the most indulgent in Austin and cherry blossom ones in DC. In Chicago, one doughnut purveyor that is repeatedly featured in all “must eat” food lists was Stan’s Doughnuts. Housed in stores that exude a very quintessential American diner feel, complete with watery black coffee (read, not coffee in the eyes of this Melbournian) and an unabashed fast-food-chain-restaurant vibe, Stan’s Doughnuts offers a surprisingly extensive range of doughnut flavours and textures. We don’t necessarily think they are on par with Dough, Doughnut Plant or Supermoon Bakehouse in NYC, but one cannot leave the U.S. without eating a doughnut from every city, Chicago included. 😛  

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