Chicago Red Velvet Cupcake Challenge

Before I went to Chicago this summer, I heard from several sources about a few cupcake places I should try (namely, Southport Grocery and Molly’s Cupcakes). I thought it might be fun to do a cupcake comparison, and so I decided to try a red velvet cupcake at each bakery I visited. I tried a new bakery about every two weeks; I would usually walk to a spot after work for a little treat. Here’s a roundup of Chicago’s red velvet cupcake options, starting with Southport Grocery, the undisputed champion of this race.

Southport Grocery:

  • Taste Test: Southport’s red velvet was my favorite – very dense, but not dry; very rich, but not overly so. I loved the frosting; something about it seemed unique compared to the others. This cupcake was unadorned, with a simple presentation – but it’s so good, it doesn’t need to be fancy.
  • Rating: 5 sprinkles (on a 1-5 scale; 5 sprinkles being maximum red velvet deliciousness)
  • The Details: Southport Grocery | 3552 North Southport Avenue, Chicago, IL 60657 | 773.665.0100

Molly’s Cupcakes:

  • Taste Test: Very moist – I love that, particularly because some of the cupcakes on this list are lacking in that department. Also very tasty, but in a more subtle (though no less enjoyable) way than other cupcakes on this list; it’s not overly sweet, which I like. You can get it with cute heart sprinkles on top – a fun extra.
  • Rating: 4.5 sprinkles
  • The Details: Molly’s Cupcakes | 2536 North Clark St., Chicago, IL 60614 | 773.883.7220

Sprinkles Cupcakes:

  • Taste Test: Moist (I hate that word, but there’s no way around it) with crazy sweet frosting. The frosting is perhaps too sweet. I also love the presentation – both of the cupcake and of the store itself. Modern, fun details.
  • Rating: 4.5 sprinkles
  • The Details: Sprinkles Cupcakes | 50 East Walton Street, Chicago, IL 60611 | 312.573.1600

Sweet Mandy B’s:

  • Taste Test: Flavorful but not incredibly special – though it was hard for me to figure out what was missing. Simple presentation, with cupcake and frosting and nothing more. The shop itself is very cute – super floral and girly.
  • Rating: 4 sprinkles
  • The Details: Sweet Mandy B’s | 1208 West Webster Avenue, Chicago, IL 60614 | 773.244.1174

Magnolia Bakery:

  • Taste Test: I love Magnolia’s cream cheese frosting – darn near unbeatable. The red velvet cake itself is less special, which is sad; it felt a bit dry. But, oh man, the frosting.
  • Rating: 3.5 sprinkles
  • The Details: Magnolia Bakery | 108 N State St #128, Chicago, IL 60602 | 312.346.7777

Swirlz Cupcakes:

  • Taste Test: Not related to taste, but I love Swirlz’s slogan – “cupcakes make people happy.” Indeed. The cupcake was also beautifully decorated, with a nice little flower atop it. However, as far as taste goes…not so much. The red velvet cake was a bit bland.
  • Rating: 2.5 sprinkles
  • The Details: Swirlz Cupcakes | 705 West Belden Avenue, Chicago, IL 60614 | 773.404.2253

What’s your favorite spot to snag the perfect cupcake, in Chicago or elsewhere?

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