The Chicago Cupcake Taste Test (First Impressions)

The first question I know you’re wondering is how this little adventure came to be. It all started about a week ago, when yours truly and her friend Ashley wanted to go to the Air and Water Show. After some mishaps with Uber, police officers on ponies, a weed truck, and a whole lot of traffic, we ended up at Sprinkles Cupcakes. After innocently (or not-so-innocently) commenting that More was right around the corner, Ashley and I ended up going on a mini cupcake crawl that day.

I even pushed back a date that I had that day, but now that I know how that date turned out I wish that we had just gotten cupcakes that day…

We decided that we would postpone our *real* cupcake crawl to another day, after adding a whole bunch of places and mapping things out. So, here are the fourteen places that we chose for our cupcake crawl.

This post is going to be about the bakeries/cupcakeries themselves, a general first impression and little description about each one. Mostly because it’s late now, and Ashley and I trekked around Chicago hunting for cupcakes. We have decided to taste test them tomorrow, and they are all sitting comfortably in her fridge.

Anyways, here are the places we went to:

1. Chicago Cupcake, 1415 N Milwaukee Ave, Chicago, IL 60622

Cheesecake based cupcakes–the whole place had a very chill, down to earth, and hipster-y kind of vibe. Located in Wicker Park, it is tiny and easily passed by the average pedestrian. The girl working the counter was by far our favorite, because she was actually intrigued about my blog and this little experiment.

2. Sweet Mandy B’s, 1208 W Webster Ave, Chicago, IL 60614

Literally the cutest. It looked like something out of a little kid’s bedtime story, and I couldn’t help but “aw” at a father and his little girl having cupcakes in the pastel-covered room, next to some light pastel floral prints hanging on the mint-green wall. It’s definitely a traditional kind of place, but in that fairytale bakery kind of way.

3. Swirlz Cupcakes, 705 W Belden Ave, Chicago, IL 60614

The people working at this place boasted that they only thing they do not make in-house is the fruit used in their cupcakes. Icings, brittles, toppings, it’s all made fresh in-house. These cupcakes by far, were visually my favorite.

4. The Twisted Baker, 2475 N Lincoln Ave, Chicago, IL 60614

A typical college cafe, located near Depaul. It’s very cozy and comfortable, the perfect place to write a term paper or write some song lyrics.

5. Small Cakes: A Cupcakery and Creamery, 3054 N Greenview Ave, Chicago, IL 60657

It looked like a little factory, but this place reminded me of what Max and Caroline would come up if the show were real. The place was decorated and accented in the signature hot-pink that adorns the cupcake boxes, it definitely has a very fun and girly vibe.

6. Sweet Sensations Pastry, 1918 W Montrose Ave, Chicago, IL 60640

This place seemed very old-school cool, kicking it back to the 1950’s or 1960’s. It was the furthest place we went.

7. The Cupcake Counter, 229 W Madison St, Chicago, IL 60606

This place is TINY, and tucked away among the busy shops in downtown Chicago. By far, the most antiquated, and old-school bakery we visited.

8. Flirty Cupcakes, 1030 W Taylor St, Chicago, IL 60607

It had the same kind of cafe-vibe, but definitely with a twist. This place seemed like the the re-vamped version of a college town cafe, the decor was very home-y, but also a little bit rustic chic. The garage theme was also very cute.

9. The Skinny Piggy, 1214 W Taylor St, Chicago, IL 60607

By far my favorite menu- this place is like a bakery with a bad-ass twist. The massive chalkboard mural was completely awesome, as was the topping bar for the cupcakes. Definitely a unique place.

10. Sugar Bliss Cake Boutique, Heritage At Millennium Park, 115 N Wabash Ave, Chicago, IL 60602

Quite honestly, it just seemed like your average cupcake shop. There was nothing that really made it stand out.

11. Magnolia Bakery, 108 N State St #128, Chicago, IL 60602

A classic. The feminine, country-chic decor of this place is just classic. The light pastel blue accenting mixed with the dusty rose gave this place a shabby-chic kind of vibe, with definitely more emphasis on the chic.

12. Sprinkles Cupcakes, 50 E Walton St, Chicago, IL 60611

Is it necessary for me to describe Sprinkles? I mean, c’mon, there’s practically five hundred in the US alone…

13. More, 1 E Delaware Pl, Chicago, IL 60611

A smaller space, but there was definite emphasis on the fact that this was supposed to be a cupcake boutique, and an elevated experience compared to the typical bakery. I will admit that the lighting was a little dark for this place.

14. Molly’s Cupcakes, 419 E Illinois St, Chicago, IL 60611

Although this is the newer location, I have a strong dislike for the Molly’s in Lincoln Park, which I will not let affect my opinions. This Molly’s is decorated like a classroom, which I think is a really cute, and innovative idea. Each cupcake was given a superlative to match the theme, which I really think is such a phenomenal idea.

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