Nowhere has a donut game as strong as Chicago's. It's not a question of where to get good donuts—it's a question of how many good donuts you can fit in your stomach before it explodes. Obviously, the stakes are pretty high. This is the master key of Chicago donut crawls, extensively researched so that you too can visit five donut shops in one day and still snap some ramen for dinner.
Stop 1: The Doughnut Vault
The Doughnut Vault is literally the size of a closet. But the River North bakery compensates for this by selling some of the largest and most delicious donuts in Chicago. Come here first because the store sells out early.
My recommendations:
Donut Holes (eat 1) OR Apple Fritter (eat 1/5)
Stop 2: Firecakes
If you like sweet and showy, this is the place for you. Have an Instagram? Even better. Focused primarily on taste? Maybe not. Fricassees is definitely good, but this is the place to cut portions if you are going on the whole crawl in one day.
My recommendations:
Coconut Cream (eat 1/8-1/4) OR Seasonals/Specials (eat 1/8-1/4)
Stop 3: Glazed and Infused
This is where the sugar is really gonna start to weigh you down. Deep breaths. Stay strong. Glazed and Infused is probably the most famous donut shop in Chicago, and this distinction is well-deserved. If you are especially ambitious, you can order a donut large enough for 16 people.
My recommendations:
Maple Bacon Long John (eat 1/4) OR Seasonal Donut (eat 1/5)
Stop 4: Do-Rite Donuts
This is it. The. Best. Donuts. Period. Keep it simple here: go for the Glazed Old-Fashioned. This should go without saying, but the vegan donuts are not the right choice here.
My recommendation:
Glazed Old-Fashioned (eat 1/2)
Stop 5: Stan's Donuts
At Stan's, don't be afraid to get creative. At any given time, Stan's has dozens of different types of donuts on display. They all look good. Yes, they still look good even after eating four donuts directly before.
My recommendations:
Lemon Curd Bismarck (eat 1/4) OR Double Chocolate Cake (eat 1/4)
Best of luck and happy eating!