Cities take on a certain magical quality during the holidays. The lights and decorations transform the urban landscape into a glittering space that brings joy to even the Scroogiest of hearts. An air of nostalgia tickles the brain in just the right way so that not even the gloomiest days can ruin the experience. Chicago is no stranger to the magic of the holiday season. While the city is known for soaking up every minute of summer, locals also love to embrace every moment that celebrates this festive time of year. 

Being a local to Chicago makes me one of the luckiest people when it comes to a staycation. Instead of airfare, I pay a round-trip price of $16 to get to and from the city and can plan a trip around hotel prices. Plus, the location can’t be beat. Even New Yorkers get out of their city when they take a staycation. I mean, that’s why the Hamptons exist, right? When I’m desperate to get away but don’t have the time or bandwidth to plan an actual trip, I’ll open Hotel Tonight or check a few of my favorite hotels in the city to see where I can find the best price…