Elisa’s Windy City Cupcake Adventure!

Traveling to new cities in the U.S. is something I always enjoy. Who wouldn’t? New food, shops, people, transportation, museums, art, culture, cupcakes… the experiences I have in each new city are truly the souvenirs I bring home with me. Recently my Aunt Jodi and I decided to hop on flights from our respective cities, Baltimore for me and Cleveland for her, and meet in Chicago for a weekend visit with her other niece Jamie (and Jamie’s boyfriend too!). And what trip would be complete without cupcakes?

Not only had the Crusaders done research and created a list of different cupcakes places in the Chicago areas I would be visiting, Jamie knew of a cupcake baker who delivered and had a dozen cupcakes waiting for me to try upon my arrival! Also, while out exploring the city, Jodi, Jamie, and I also visited a place in Wicker Park called “bake” to sample their cupcakes. Below are a little about the cupcakeries, and of course reviews!

Flirty Cupcakes – Delivered to Logan Square! (Storefront in West Town Area)

Flirty Cupcakes is a shop (called the Dessert Garage), cupcake truck, and delivery service that began with a spark of nostalgia and a love of cupcakes. After seeing an old ice-cream truck, the owner was inspired to create that same feeling of excitement she felt as a kid when the ice cream truck drove by, but for adults and with cupcakes. While I did not get to visit the Dessert Garage, the photos on their website are really cool and it was reviewed by one of my other favorite blogs, Design Sponge. The next time I am in Chicago visiting, the Dessert Garage will definitely be on my list of things to do. But back to the cupcakes…

The “Flirty” Dozen! (A VERY special thank you to Jamie for getting these!)

While almost every cupcake in the box made me go Mmmmmmmm, (and yes, I did try all 12), my three favorites are the following: (Cupcake photos from Flirty Cupcakes’ website, no harm or infringement intended – they are much better than my photos turned out!)


Peanut butter and chocolate is a favorite combination of all the Crusaders, so this cupcake with its peanut butter cup topper immediately stuck out to me! It was clear what kind of cupcake this was, however, I would not have guessed that it had a peanut butter ganache filling – I’d never even heard of peanut butter ganache! Smooth, creamy, sweet, savory, this filling complemented the richer and thicker chocolate ganache on top and the moist chocolate cake. I like cupcakes that balance sweet and savory, where each flavor can be tasted on its own, but together create a whole new flavor sensation; and this peanut butter and chocolate cupcake achieved that perfect balance.

The McDreamy

Dr. Derek Shepherd may not be a cupcake, but if his good looks were edible, they would be this cupcake! The moist chocolate cake with cream cheese and chocolate morsel filling was very much like a “black bottom.” With smooth and “dreamy” cream cheese icing on top, the decadence of this cupcake becomes clear, and makes you want another.

Devil in Disguise

Finding a good red velvet cupcake anywhere can be difficult, as you have seen in our many many posts, but at Flirty Cupcakes they have this flavor nailed. The almost impossibly moist cake is not just topped with their delightfully dreamy cream cheese icing, but also filled with it! Great red velvet AND filled? I think I met my cupcake soul mate!

Check out all the flavors they have to offer, listed on their website, and if you are in town, stop by the Dessert Garage, find the truck, or have some delivered to your hotel! It’ll be worth it!

BAKE – Wicker Park Area

BAKE attracted me right away when I read on their website about the husband and wife baking duo, who both loved sweets since childhood and have 30 years of combined baking experience. After we shopped and ate lunch in Wicker Park, we walked over to see what sweet confections they had to offer. We almost missed the shop, as the sign was small and hard to see on the window, thank goodness for smart phones with maps!

It was later in the day on Saturday, so our cupcake flavor options were limited, but we settled on a Nutella Malt Cupcake – that was HUGE! Definitely enough for the three of us to share, we cut it up and tasted while soaking in the shop decor. Cute “bake” signs clumped together on one wall, with fun patterned fabric canvases on the opposite wall, huge windows, fun vintage plates, and friendly staff all complement this little shop.

Now for the cupcake review:

Nutella Malt

This cupcake was good, but not phenomenal. The cake was moist and buttery, as was the icing, and neither were overly sweet (which is a plus for me) but I yearned for more of that hazelnut and cocoa flavor that is so specifically Nutella. And I love malt anything, but missed it completely in this cupcake, minus the malt ball on top.

I would definitely go back to BAKE and give their cupcakes another try; and had they not been so large, perhaps I would have tried the Vanilla Vanilla and Chocolate Vanilla flavors they were offering that same day. Next time I would like to try some of their other baked goods, because they had a S’mores Brownie that looked divine!

Both Flirty Cupcakes and BAKE were great, and definitely cupcakes I wouldn’t mind eating the next time I am in the Windy City! Seeing the sites, shopping in the vintage stores, visiting the Art Institute, eating some fantastic tacos, and of course eating great cupcakes are all souvenir memories I brought back with me. But most of all I loved spending time with my wonderful Aunt Jodi and her amazing niece Jamie. I can’t wait to plan my next “new-to-me” city adventure and find some cupcakes to taste!

Have you been to the Windy City, or live there? If so, what’s your favorite Chicago cupcakery?

– Posted by Cupcake Crusasder, Elisa (Baltimore, MD)

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