Planning Tips and Tricks

Seasonal candy corn cupcake from Phoebe's Cupcakes.

Invite Friends
A Cupcake Crawl is always more fun with friends along. A group of five to six people is ideal. A lot of cupcake places are pretty small, so it can be hard to get in the door with larger groups. It’s also easy to fill up on cupcakes, so it’s important to have friends to share cupcakes. That way, you can all try more flavors.

Map it Out
Select one of my routes or create your own. Print out the maps with addresses or pre-program them into your cell phone. Google maps will help you plan routes and transportation options between bakeries. The day always goes more smoothly when you plot the course in advance and make sure bakeries are open. Estimate about 45 minutes per cupcake establishment both to eat your cupcake and to travel to the next spot.

Use the CTA planner to check comings and goings.

Double Check Transportation
Public transportation options are available for the majority of the city’s bakeries. However, it’s best to use the CTA’s planner to verify station openings, bus routes, and wheelchair accessibility.

Pack Essentials
Most bakeries are in neighborhoods with drug stores but you can’t always find what you’re looking for. Bringing simple conveniences like a package of hand wipes and a bottle of water can go a long way toward making your Cupcake Crawl more enjoyable. Also consider packing a street map, an umbrella, sunglasses, your cell phone, and your camera! Check out our Cafe Press store for cool gear!

Greens will help you recover from sugar shock.

End With Salad
At the end of every Cupcake Crawl, you’ll no doubt crave leafy greens to counterbalance the sugar shock. Plan your day so that the last place on your Cupcake Crawl itinerary is near a healthy dining option.

Record Your Results
As you try different cupcakes, be sure to take good notes. Then, record your ratings here when you get home. A running tally of results will be kept on the site, and we’ll see who has the top-rated cupcake. Have great cupcake photos? Share them in the “We Love Chicago Cupcakes” Flickr group.

Buy Now