I recently went on a quick, weekend trip to Chicago and despite the default Chicago food goal of eating deep dish (which we accomplished) my sister convinced us to go on a doughnut tour. I can now confirm that I've eaten a LOT of doughnuts in Chicago. Overall, the doughnuts in Chicago did not disappoint! Here were our two favorite places to eat those pillowy, doughy treats.
This little hole in the wall was very cozy and cute. They also have a small outdoor seating area which would be perfect to enjoy your treats on a nice day. We tried the triple chocolate doughnut (see above) and it was moist, crumbly and full of chocolate flavor - everything you could want in a cake doughnut. We definitely would've gone back for more but were limited by the shortness of our trip.
These were more your typical doughnuts and we nabbed the red velvet doughnut, which had a fantastic cream cheese icing. This store is hidden inside of another restaurant and can be slightly confusing to find. Make sure to follow the signs! The inside had seating space and an amazing display of doughnuts.