- $11 for four signature red velvet cupcakes
In 1905, John Roeser Sr. came to Chicago from Germany intent on opening a wholesale bakery business. Six years later, he became the proprietor of Roeser's Bakery. Since featured on Food Network and Chicago Channels 2, 7, 9, and 32, business has boomed ever since he first opened his doors. In 2011, the business celebrated its 100th anniversary, making it the oldest family-owned bakery in the city. Today, it's run by third-generation baker John Roeser III and his wife, Deb. Though some equipment and baking techniques have changed over the last century, much remains the same: Roeser's still stands out on North Avenue thanks to its bright neon marquee and their custom-made cakes are still made with high-quality ingredients.