Wikipedia, cupcakes date back to at least 1796. So in one shape or another, I imagine that gourmet cupcake emporiums have been around for ages. But I have only been aware of trendy little cupcake cafés popping up around Chicago for about the last 2-3 years.
For the preservation of my arteries, the relative recency of the cupcake craze is probably a good thing. Because in the category of "Sweet treats that I shouldn't eat but sometimes still do," cupcakes have surpassed Eli's cheesecake, Portillo's chocolate cake, Krispy Kreme donuts (are they still around anymore?), pecan pie from Baker's Square and pretty much everything else as my gluttonous fix of choice.
Unlike the aforementioned sweets, for which I have a very specific favored purveyor (not that I refuse chocolate cake, pecan pie, donuts or cheesecake from most elsewhere), having a cupcake--and where from--is a choice predominantly based on convenience. For although there seem to be several more cupcake joints around town than there were five years ago, most bakeries have just one location and if I am in the neighborhood of any at a time that I can justify--er, rationalize--the cost and calories, I typically find the experience truly scrumptious, whether it's one place or another.
That said, there are three cupcake shops that so far rank as my favorites in the Chicagoland area. This shouldn't be taken as a comprehensive survey, as I haven't been to all that many places and at least one that I liked has already come and gone. But rather than embark on a comprehensive cupcake gorging expedition, let's consider these the best of what I've found so far--of shops visited at least twice, so as to sample a variety of flavors--and I'll be sure to update you if I discover anywhere else that truly "takes the cake."
Before my three medalists, let me give a shout out to three other cupcake bakers. Mrs. A's Cupcakes & Cookies at Old Orchard Mall in Skokie doesn't really create the same type of beautifully-decorated gourmet cupcakes as the top three, but does an excellent job with the basics, including chocolate fudge and red velvet varieties. Foiled Cupcakes is a delivery only cupcake bakery in Naperville, so you can't just stop in, but their creations were provided at a Meetup I attended and the two cupcakes I had were phenomenal. Their delivery reach is pretty extensive and the proprietor does a great job of promotion via Twitter, so keep them in mind for your next event. Although Sweety Pies Bakery is in my hometown of Skokie, I have yet to visit, but they have gotten some good reviews on Yelp and if their home page photo (above) is to be believed, they make the most beautiful decorated cupcakes I've ever seen.
But now that I've whet your appetite, and mine, here are my choices for "The Best Cupcake Places in Chicago," in reverse order (to be clear, I'm ranking establishments, not specific flavors of cupcakes):
Molly's Cupcakes - 2536 N. Clark, Chicago
This popular Lincoln Park café certainly fills the bill in making delicious cupcakes in a variety of flavors. But with nearby parking often hard to find, popping in for a cupcake isn't always all that practical except for those who live in the neighborhood. And compared to my top two choices, Molly's cupcakes are somewhat small and pricey, not particularly original and on at least one visit, not exceptionally moist.
So although it's pretty hard to make a truly bad cupcake and Molly's certainly doesn't, I've had cupcakes just as good at the now-gone Chicago Cupcakes (on Briar Place, near Broadway) and would expect to find similar quality or better at other cupcake bakeries, including Phoebe's (3327 N. Broadway), which I think may be run by the same proprietors as Chicago Cupcakes. What I do really like about Molly's is that it's a comfortable place to sit for awhile and they have sprinkle-shakers with which to adorn your cupcake. And I most recently had a cookie dough cupcake that was pretty awesome.
More Cupcakes - 1 E. Delaware Place, Chicago
Chicago Magazine gave this Gold Coast emporium a couple of citations, including noting their launch of a cupcakemobile, a good idea if I've ever heard one. Helped by a "15 minute loading zone" in front of the shop, which has scant or no seating (I can't recall), I've stopped in a few times now. I would have to say that More takes the cake in terms of originality, combining sleekly designed cupcakes like the red velvet at left, with unique flavors such as "salted caramel" and over-the-top extravaganzas like their version of cookies & cream, one of many varieties that feature a creamy filling.
More is clearly the most gourmet of the cupcake places I've visited, with the industrial design of their single-serve cupcake boxes rivaling the ingenuity of Apple (I've been tempted to tell the clerk, "just throw it in a bag; it'll be gone in about 37 seconds"). But despite the prevailing wisdom that it's impossible to be too rich or too pretty, I've occasionally found both to be somewhat true at More. While beautiful, the red velvet cupcake in particular wasn't quite as heavenly or unique as I was expecting (although it was certainly more than adequate). So while this bakery is excellent and well worth several More visits, at least in my humble opinion, their cupcakes can be topped.
#1. Sensational Bites - 3751 N. Southport, Chicago
Located up the block from the Music Box Theatre, this accurately-named "dessert cafe"--two of my friends rave about their chocolate caramel brownie--has benefited from my relatively newfound affinity for world cinema and I've enjoyed sampling a new cupcake (or sometimes two) on each visit.
While neither their flavors or designs are as unique or elegant as More's, they have a good assortment of cupcakes both basic and fancy, including a few with fillings. I've had their red velvet, cookies & cream, marble (at left), orange dreamsicle and a couple of others and have never been disappointed. Especially as their cupcake prices range from $2.50-$2.75, about dollar less than anything at More and most choices at Molly's. I've occasionally found their counter help to be a bit gruff, but nothing to keep me from coming back and enjoying Sensational Bites again and again (in moderation, of course).
If there are any places I haven't yet tried (or just didn't include) and should particularly know about, by all means don't keep your favorite cupcakes under wraps. As time and my blood sugar levels will allow, I'll be happy this investigation open. Preferably with a glass of milk.