Rating Chicago’s best sweet sensations—and a surprise winner!

Argue if you must. But here are the highly unofficial results of a poll of one (me) for best Chicago-area sweet-tasting delights.

Shockingly, number one is an out-of-the-box, deep-from-left-field entry, stunning the entire field of contestants. But no peeking at the bottom of this page.

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Better to savor the flavor (described below) of each and every one as we go:

10) The Salerno Butter Cookie. Tons of cookie candidates here (see No. 9 for another one), but oh man, are there any that have stood the test of time like the Salerno Butter Cookie? Not a bursting sweet sensation, but buttery, smooth, and so comfortably sweet. Dip it in milk? Absolutely!

9) The Oreo Cookie. Enjoy it now, because this will be the last of our cookie candidates. How can you leave out the exquisite Oreo, another that has stood strong through the test of time? Whether you dip it in milk, for that unique but unforgettable squish-sweet sensation in your mouth, or you go old school and separate the chocolate cookie parts and scrape off the white frosting, either way, the Oreo Cookie is just flat out delicious. On tradition and longevity alone, it makes this list.

8) Marshall Field’s (now Macy’s) chocolate Frango Mints. Heaven shaped in a small cube. Thick when you bite into them, but ridiculously rich with taste. A perfect blend of the chocolate and the mint. Nuff said.

7) Bakers Square French Silk Pie. Yes, I know, Bakers Square closed many of their locations, and is harder to find now, but that French Silk Pie is what everybody “dies for.” Honestly for me? A little too rich for my taste, but I have been badly out-voted by the adoring throng of pie lovers in the Chicago area, who almost immediately think of the French Silk Pie with just the mere mention of the old Bakers Square Restaurant.

6) Garrett’s Caramel Corn. Would be No. 1 if we were just rating on smell alone. Ever walk by the store? If the wind is blowing just right, and the popcorn smell emanates out of the store onto the street and into the unsuspecting nostrils of a passerby? It’s almost unfair. Impossible not to be drawn in and buy a bag of that precious sweetness. Warning: Definitely not recommended by the American Dental Association (but wow, does that Garrett’s popcorn taste good)!

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5) Portillo’s Chocolate Cake. A Chicago sweet classic for many years. The perfectly puffy cake stands proudly erect as it is served to you in its way-too-small dish, almost making the cake sitting there seem majestic.  But then you bite into it, with its velvety chocolate sweetness? And oh my goodness, so good. Comes in milkshake form, too, which quite frankly should not even be allowed. Just way too tempting.

4) Fannie May Candies. How do you pick just one? We tried but just couldn’t do it. Instead, we are giving the award to the entire candy selection. One bite does the trick—you know immediately you are tasting sweet greatness. Also, as a bonus, Chicago fans know Fannie May is our very own. That makes those candies taste even better!

3) A surprise here… but we are going back to our favorite pie shop, Bakers Square. Their irresistibly good Banana Cream Pie shoots up the charts! Unlike the French Silk, the Banana Cream Pie doesn’t blast you with sweetness, but instead destroys your taste buds (we say this in the nicest way possible) with a creamy, smooth silkiness that just kind of melts in your mouth. The crust? To die for, but the real kicker here is the mouthwatering cold whipped cream that tops this sweet sensation. A dessert of just the crust with the whipped cream—forgetting about the banana cream filling—could probably finish in our top ten. That’s how good it is.

2)  Eli’s Cheesecake. Was there ever a doubt that Eli’s sinfully good cheesecake would be near the top of the list, second only to an outside intruder? But in Chicago proper, there is none more famous, none more delicious. Just the right texture, just the right amount of sweetness, just the right ratio of filling to crust. Which one is our favorite? Forget about trying to choose. Going over all the flavors and possibilities could be a separate essay unto its own. Don’t complicate things; just take a bite and enjoy the best Chi-town has to offer.

1) OK, we had to sidestep just a bit… bend the rules slightly, and go outside Chicago proper for the absolute, unquestioned king of finest dessert tastes. 

Let me take you all the way to West Allis, WI, and the Wisconsin State Fair, and introduce you to the greatest thing you have ever tasted. The Wisconsin State Fair Cream Puff. Baked and made to perfection right in front of your very eyes. You can actually see them being made while you wait in the winding line to pick them up, with the anticipation and the visuals making up part of the thrill.

Order one? Two? Better yet, go with the dozen pack and bring some home for the family, friends, and neighbors. But make sure you eat at least one on site right there. The warm sensation of the freshly baked pastry mixing in perfect harmony with the cold, more than ample cream filling in between is truly amazing.

Tough to be on top, with so many great contenders in that list above and more… but Wisconsin State Fair Cream Puff? Step up, my fine friend, and take your rightful place atop the medal stand—and accept the award as the No. 1 sweet taste sensation.