For many, the first Friday in June represents the start of fun-filled summer weekends that boast cool drinks, relaxing nights on the patio, and off-the-shoulder shirts that have been hiding in your closet since you purchased them on sale last October. But for me, a doughnut-fanatic that runs a food blog specifically focused on the fried dough confection, this day is essentially Christmas. Last year in celebration, my sister and I trekked to downtown Chicago from our home in the suburbs for a dozen doughnuts from a place known for their high-quality treats and unique flavor combos. We were not disappointed and decided that this year, we needed to go bigger and better than we had before. The solution seemed simple: a doughnut crawl through Chicago's most well-known doughnut shops. 

A Brief History

National Doughnut Day is observed by the United States every year on the first Friday of June, and while it may seem like a totally millennial holiday, the celebration has been around since 1938 when it began as a fundraiser for Chicago's Salvation Army. Knowing that we were headed to the birthplace of National Doughnut Day for our crawl was simultaneously comforting and worrisome. We would have our pick from tons of great doughnut shops, but the people of Chicago would surely all be out and about trying to get their hands on a delicious doughnut to kick off the weekend. 

The Plan

We decided we would get an early start and head out around 8:00 am, getting pummeled by rush hour traffic but nonetheless on the hunt for doughnuts. I had made a list of my favorite places and several new places that I had yet to try, grouping them into neighborhoods. The Fulton Market District often has greater parking options than other neighborhoods, so the plan was to park there and to take Lyfts around to other neighborhoods. We would go to as many places as we could and would play the whole thing by ear as we traveled around the city.

Do-Rite Donuts

Do-Rite Donuts was where we went last year for National Doughnut Day, so we thought it would only be right to start our crawl here. The establishment was noticeably more busy this year than last, and they were out of their signature red velvet cake doughnut (my favorite doughnut in the entire world). We were super hungry and got two doughnuts: the Pistachio Meyer Lemon and Orange Olive Oil Vegan. Both definitely had significant citrus vibes and were a great way to start our day, but we knew we had a ways to go in terms of the doughnuts we would be consuming. We left half of each uneaten and headed to our next location, hoping for something more chocolatey and decadent. 


We walked a few blocks east and found ourselves at BomboBar, a fast-casual walk-up eatery that offers Italian treats and coffee to go. Probably their most popular item is the bomboloni, which is what we were there for. Bomboloni are Italian hole-less doughnuts, and at BomboBar they serve them with small squeeze bottles to infuse your doughy treat with more deliciousness. I had read that they would have a special gelato/bomboloni sundae for National Doughnut Day, but unfortunately the rumors weren't true. We got one s'mores bomboloni and were blown away by the flavors and the warm dough. We even got a free plain bombolone, which was perfect because two people sharing an infused doughnut (aka very messy) doesn't usually go over well. It was super cold and windy that day in Chicago so this warmed us right up.

Doughnut Vault

We took a Lyft into the River North area and were super excited to try some of the old-fashioned doughnuts from Doughnut Vault. Unfortunately, they were already sold out when we arrived and we joined a group of confused and frankly quite angry Chicago doughnut fans. 

Firecakes Donuts

At this point, we were still hungry for doughnuts, though the initial craving had worn off. We were feeling discouraged after our stop at Doughnut Vault, and the gusty Chicago winds were getting to us and our thin jean jackets. A short line outside of Firecakes didn't deter us from our next round of doughnut bliss. The shop had no space for seating, so we grabbed our doughnuts and hastily ate them in the outside seating area as our windblown hair whipped around. I got key lime pie and my sister got malted milk, both of which were truly delicious. I definitely want to go back here at a less-crowded time to try their unique flavors (especially the matcha donut!).

Uptown Donuts

At this point in the day, eating doughnuts was beginning to feel like a chore. We felt kind of gross, but three doughnut stops definitely did not constitute a crawl. We decided to try out a new donut place that had just opened in Uptown. We were back in our car where there was warmth and water, so we were refueled and ready for more when we finally got to Uptown. While this place might not have the Instagrammable factor that the other places did, it was the only place we went with comfortable indoor seating and no lines. We grabbed two doughnuts, one matcha glazed and one ube glazed. Whether or not they actually tasted like matcha and ube, they were sweet and colorful and solid capstones to our crawl. 

The Aftermath

Once we made it back home, my sister and I both collapsed in our beds and practically slept for the rest of the day. We were definitely crashing hard after the carb and sugar overload. I could barely edit my doughnut photos without feeling uneasy. Never had I craved a vegetable so much in my life. Nonetheless, this was a fun and adventurous way to celebrate National Doughnut Day that I will remember forever. Chicago knows how to do Doughnut Day right, and to get a high quality doughnut on this holiday requires planning. My love and appreciation for these beautiful desserts remains stronger than ever. But would I do a doughnut crawl again? I don't quite know if I'm ready to say yes to that yet.