Our first stop was Sensational Bites (located at 3751 N. Southport Ave), and yes, it actually was sensational. The cupcakes at SB (yeah, we're on that kind of basis) were my second favorite in all of Chicago. The shop was super cute and perfect for the freezing cold (um, it was 0 degrees) snowy weather. SB had a huge selection of all kinds of baked goods, including tons of cookies and cupcakes. Beth and I sat in the shop for a while, eating cupcakes, sipping on coffee, and warming up. The cupcakes were perfectly sweet and the presentation was beautiful. Amazing start to our crawl.
Sensational Bites on Southport.
Vanilla cupcake with vanilla buttercream frosting $1.65
Chocolate peanut butter cupcake $1.75
And they get extra points for having Patriots cookies
Our next stop was Southport Grocery (located at 3552 N. Southport Ave.), an adorable little gourmet store/cafe/bakery. We spent a while just browsing the store, which is filled with gourmet food, books, and prepared foods. The cafe looked like a great place to lunch, but we only had cupcakes on our mind. So we picked up two and brought them home for later. They only had vanilla and chocolate, so if you are in the market for variety, Southport Grocery probably isn't the cupcake place for you. Also, they're not fancy-looking; just your basic cupcake. They tasted good, but weren't our faves; the cake tasted a bit too much like corn bread and the frosting was super sweet.
Southport Grocery and Cafe
Chocolate and vanilla cupcakes with buttercream frosting $2.00
Saturday was a new day and we had renewed appetites for cupcakes. Our first stop was Swirlz (located at 705 W. Belden). This shop is tiny and has a huge case just filled with all kinds of cupcakes. I love the fact that the cupcakes say "happy" on them. Swirlz also has lots of cupcake merchandise and I snagged an over-sized coffee mug that says, "Cupcakes make people happy." Yes, they do. I'm still mad at myself for not getting a t-shirt, too. Again, the cake part of the cupcake was a little too much like cornbread, but I would definitely go back to Swirlz. They have a huge selection, including a daily "surprise" cupcake. We tried the mint grasshopper and it was delicious.
Image from Planet99
Swirlz Cupcakes
Vanilla with vanilla buttercream frosting $3.00
Chocolate with vanilla buttercream frosting $3.00
Mint grasshopper surprise cupcake $3.00
While en route from one cupcake place to the next, I happened to see a giant blue and orange sign out of the corner of my eye. "Cupcakes...cupcakes...." I started stuttering. "Why isn't that on our list??" Adam swerved the car over, parked (much easier to do in Chicago than in Boston) and thus we found my favorite cupcake place in Chicago. Molly's Cupcakes (located at 2536 North Clark St.) has a fun, youthful atmosphere. It's a pretty big shop and has vintage toys decorating the walls and retro board games for you to play while you eat your cupcakes off of grandma's mismatched china with real silverware. There's a bar area where you can sit on giant wooden swings. And there's even an area where you can add toppings and decoration to your cupcakes. The cupcakes were the PERFECT amount of sweet and the frosting just melted in my mouth. The kind of cupcake that just makes you smile with every bite. They definitely weren't the prettiest of cupcakes, but maybe we could have remedied that if we added more decorations on our own.
Molly's Cupcakes 
Vanilla with vanilla buttercream frosting $2.00
Chocolate with vanilla buttercream frosting $2.00
Carrot Cake $2.00
Image from YelpSwing Seats at Molly's
Your cupcake crawlers loving Molly's 
Cupcakes
Chocolate with pumpkin frosting $3.00
Image from Cookie magazine
Warning: after completing our cupcake crawl, I didn't even want to think about cupcakes for a month straight, so be prepared. It was so worth it, though. And I think I'm finally ready to gear up for the Boston cupcake crawl (as soon as Beth and Adam get here). Boston, get your cupcakes ready for us.
Caroline says
This is awesome... from a Chicago cake lover, I am embarrassed to say I have not tested ALL these places. I am marking my calendar!!!
~Angela~ says
I used to live down two blocks away from "Cupcakes", and they disappointed me the two times I tried them out. Something weird with the frosting, I think. I still ate them, but I wanted them to be so much more than they were...
legallyheidi.com says
they all look so fabulous! If you're ever in dc...be sure to try out Cakelove on U street, NW for their cupcakes. They are to die for! 🙂
Sara says
i'm so excited you posted this!!! yummmmmmm. we need to do a boston cupcake crawl one of these days!
Jenn says
I'm making this a goal.
Ben says
All those cupcakes look so fantastic. I will keep this guide in mind next time I go to Chicago.
Cheers!
pbandrazz says
um yes, we have the best cupcakes.
and sweet mandy b's is my favorite. you must go next time you are in town.
nicoleantoinette says
I'm pretty upset that we're not real life friends. This rules.
Peter says
Never read this blog on an empty stomach. Never read this blog on an empty stomach.
Joy @ Big Time Fancy says
I almost rented an apartment above "Cupcakes" but chose not to as I figured I would be entirely SICK of cupcakes after a few months of living there. And that would be a damn tragedy.
Sensational Bites is my very favorite, though.
d says
after all that sugar i'm glad you made it out on the town!
let me know next time you're here and i'll partake in the sugary part!
Michelle & the City says
chocolate with pumpkin frosting?! sounds like heaven 🙂
design for mankind. says
OMG you girls are ADORABLE! And gracious, I miss Chicago. 🙁
Husmusen says
Oh I love the cupcakes and your blog!
bethannept04 says
Sues - We're counting down the days to Cupcake Crawl Part II, Boston Edition 🙂
cdp says
CHOCOLATE WITH PUMPKIN FROSTING??
Sweet Baby Jesus.
Lippy says
I just wonder how much people would laugh at me if my first trip to Chicago were inspired by a craving for some of those CUPCAKES!
LOL, man, I need me some cupcakes now, and it's very late!
Gjelly says
This was so helpful! I'm going to Chicago in a month and my friend and I are going to throw a baby shower for another friend at Molly's Cupcakes. I can't wait! 🙂
Babycakes says
Oh my god, those cupcakes looks beautiful. I will remember that - Chicago for cupcakes, if I ever get there. I love how Americans are so good at brownies, cookies and cupcakes.
Anonymous says
As a cupcake lovin' Chicagoan I can say I've visited all of these places and Molly's is the best of all. Great cupcakes and nice people.
Debbie Wolf says
If you get a chance to go back to Mollys (my personal favorite) try the Ron Bennington's "Ive got my own cupcake". If you like chocolate and peanut butter, its to die for.
Stephanie says
We're leaving for Chicago in 10 days (!) and are super excited to re-create your cupcake crawl!
So happy to have found this blog too, because in between a stop at the theatre on New Year's Eve and the NHL Winter Classic on New Year's Day, we're going to be trolling the city for the best cupcakes. Thanks to you, we got a head start on the "must" places to visit 🙂
Anonymous says
Good guide. Thank you. Phoebe's Cupcakes (www.phoebescupcakes.com) just opened in Lakeview - went on opening day and they are amazingly good (tied with Sweet Mandy for best cupcake in Chicago in my book),
Monica says
I would have to agree that Molly's cupcakes takes the cake! Their cupcakes are to die for, and the employees were very friendly. Like you mentioned, it's made that much more fun by the fact that you can play Jenga or sit on swings while you eat your cupcakes!
Cassidy says
We're going to Chicago next month and I am now more excited than I already was. I just told my husband that since he's dragging me to a Cubs game, I'm dragging him to eat cupcakes. Really though, which sounds better...baseball or sweet cakey goodness topped with yummy, sweet frosting? I think the choice is obvious. 😉
Peggy says
Cupcakes on the Southside of Chicago...Stop by and see us!
Kelly says
I was so sad I moved out of chicago by the time u guys posted this! I am going back on Monday for a wedding though and I am planning a cupcrawl thanks to your awesome idea. Can't wait!
Tyler says
Is there an organized group outing or is it on a individual basis?
Sues says
@Tyler- Unfortunately, my sister and I created this cupcake crawl on our own when I was visiting Chicago years ago. But I'm pretty sure there are organized cupcake crawls in Chicago these days. And even more fabulous cupcakes!