CakeSpy Note: This is a guest post chronicling a very sweet visit to Chicago from Cake Gumshoe Ryan, whose sweet adventures can be followed via his great site, Ryan's Baking Blog! All of the text, photos, and opinions reflected below are his--read on, and enjoy!
I'm in Chicago until Friday (then I leave for San Francisco) and was super excited to grab some delicious cupcakes. I've had a few bakeries recommended to me and I tried out a bunch so far. 
Molly's Cupcakes 2536 North Clark Street, Chicago, IL 60614
I only have one picture for this section (photo pictured top), I wasn't sure if they wanted me sitting there photographing the whole store and everything so I just focused on the cupcake. I also didn't ask if I could photograph so I was trying to be sneaky (well, as sneaky as you can be with a big DSLR camera). This is a Chocolate Decadence cupcake. They have a ton of flavors ranging from this to peanut butter nutella, minty mash-up, peach cobbler, and so much more. This cupcake was amazing. Probably the best chocolate cupcake I've had. Honestly though, I think this one was meant to share. It is a chocolate cake with chocolate mousse filling, chocolate ganache on top PLUS chocolate frosting with chocolate shavings. It is a lot of chocolate and every element is so good. The cake was super moist, the mousse was smooth and chocolatey, the frosting and ganache were perfect. The shop itself is great. It is pretty large and cafe style. They have a bar you can sit at that has SWINGS. Yes, like playground swings for you to sit on to enjoy your cupcake. They also have a bunch of tables and seats to sit at, some people were working on things and a few people were having conversations. It was a really comfortable atmosphere and the staff was really nice. If all that wasn't enough to convince you to go, they have a "sprinkle station". It was a counter with shakers filled with different kinds of sprinkles, like little stars and moons or dinosaurs, that you could top your cupcake with. I thought this was a great idea. I really can't recommend this shop enough, if I lived in Chicago I'd be here every day. They are also open super early and super late. Sunday-Thursday they are open til 10pm and on Friday and Saturday til midnight.
Bleeding Heart Bakery 1955 West Belmont Avenue, Chicago, IL 60657 
I came here twice actually, unfortunately the first time I forgot my camera. 
This is a terrible picture and does not do this cupcake any justice. Like I said, I forgot my camera and had to use my blackberry. I had the Veruca Salt cupcake (above), a salted caramel cupcake with caramel filling and FOUR kinds of salt. It was amazing. The cake was dense in all the right ways, the caramel filling was delicious, the frosting was so smooth, and the salt added a ton of great flavor. My friend had a "Take A Hike" Scone, which was pretty much a trail mix scone, and he loved it. They also have a variety of vegan cupcakes in a lot of flavors. The staff was super nice and helpful, my friend had a ton of questions about the different items and the girl working knew everything. 
I came back a second time to try a red velvet and I remembered my camera. I love how it was decorated and it was super delicious, a traditional red velvet. The frosting was super smooth and creamy, I don't have any complaints. The bakery has a very punk rock feel which I thought was great. They were playing punk music, had a ton of local flyers up and do a lot of community building and clearly care about the people that live in Chicago. The tables were cut out like cupcakes, there was a couch and coffee table by the front window, and they had pretty awesome shirts for sale (if I had more money to spend I definitely would have gotten one or five). They definitely make you feel comfortable. That is a big thing that I liked about both this bakery and Molly's Cupcakes. I felt like I should sit down and enjoy my cupcake there, it was a relaxing environment and very welcoming.
Sweet Mandy B's 1208 West Webster Avenue Chicago, IL 60614
Sweet Mandy B's is a bakery in Lincoln Park with a lot of pastel colors. Their frostings were all tinted light pink or light blue or another pastel and the shop had a cozy feel to it. It's has another section for an ice cream shop and that is where the seating is. It was hectic in there so I got my cupcake to go. 
They had the normal flavors as well as orange and lemon and this french toast cupcake. It's cinnamon cake with maple frosting. This cake was made well, super soft and a strong (but not overwhelming) cinnamon taste. The frosting was a perfect consistency and it was just the right amount. It tasted exactly like french toast. They also offer a ton of cookies as well as cakes, puddings, and ice cream. It was easy to see why they had so many customers.
Sprinkles 50 E Walton St, Chicago, IL 60611 
Everyone knows about Sprinkles. The first cupcake-exclusive bakery to hit the world. They opened in 2004 and have enjoyed a ton of success. Many of their cupcakes sport the signature dot that many people have come to recognize as Sprinkles. This was the cupcake shop I was most excited about for the obvious reason: it was the first cupcake shop and EVERYONE talks about Sprinkles. I planned on going twice during my trip to sample various flavors because of how much I've heard but I don't think I'll be going back, not even to try the famous red velvet everyone talks about. 
This is the key lime cupcake, a summer exclusive flavor. The frosting has a STRONG key lime flavor and the cake has a more subtle but noticeable flavor to it. Both were delicious. The cake was extremely soft and fluffy, perfectly moist, and overall delicious. I was satisfied. 
This is the milk chocolate cupcake: chocolate cake with milk chocolate cream cheese frosting. I think the frosting really killed this cupcake for me. Maybe I'm just not a huge fan of cream cheese frosting but it wasn't that chocolatey. I wanted that candy-bar-milk-chocolate taste and I just didn't find it. This cupcake wasn't that pretty compared to the key lime I had. The cake itself was pretty good but it felt kind of doughy in my mouth. It makes me believe the Sprinkles cupcake craze is about decent cupcakes and a lot of branding. They aren't bad cupcakes by any means, but not the best I've had. The store itself has a very modern look to it. I really like modern design, especially in homes, but I like cozy cupcake shops. Mismatched furniture, comfy seats, someplace you can sit down and feel comfortable. Sprinkles only had four or five stools and a lot more customers than that, it didn't seem like they encouraged you to sit and stay.
More Cupcakes 1 East Delaware Place, Chicago, IL 60611 
More cupcakes is a small cupcake shop in downtown Chicago. Literally small. It's a tiny shop without any chairs and a small table to stand and eat at. The cupcakes are displayed in a big glass box thing. It was a little confusing and the labels were tiny, I also couldn't tell what flavors they had that day..maybe they had all of them? I had a black and white cupcake, a vanilla and chocolate cake with chocolate frosting and covered in chocolate shavings. I originally wanted a white velvet but wasn't sure if they had it (I only saw the display one). The cupcakes are taller than normal cupcakes and this one had a lot of frosting. It took three or four bites to get to the actual cake part and it was awkward to eat because of it's height. The cake was a little dry too.
They also had mini cupcake samples, I grabbed the chocolate passionfruit, chocolate cake with passionfruit frosting. I've never had passionfruit before and it turns out I don't actually like it. The man in front of me did sneak an extra sample so they must have been good. Not all the cupcakes had a ton of frosting so maybe some of the others are better. I started feeling a little sick by the end of mine though. As much as I hate to say it, I wouldn't go back there.
(CakeSpy Note: I should say that I too have visited More Cupcakes, and had a much better experience than Ryan; like so many things, it could have just been his visit, or different tastes. Any reader thoughts?)
In Closing
If you are in Chicago, go to Bleeding Heart Bakery and Molly's Cupcakes. If you're in the Lincoln Park area, go to Sweet Mandy B's. Try Sprinkles, maybe you'll like it more than I did, it ended up being more of a "cupcake history" kind of thing for me. And finally, if you're a frosting fiend, go to More. Or get one of their cupcakes without a ton of frosting.
Don't forget to keep up with Ryan's sweet adventures at Ryan's Baking Blog!