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…

Colder weather calls for cozy get togethers. If there’s one thing Chicago knows how to do well (other than take advantage of summer), it’s survive winter and the colder months. We’re a social city! We like going out for brunch and meeting friends for a cocktail after work. Five months of bitter cold won’t keep us hibernating...well, not the entire time at least. We can appreciate a good occasional hibernation. For those colder months when the tips of your fingers start to turn blue and your nose goes numb, the cozier spot to meet up, the better. Cozy, by definition, means “enjoying or affording warmth and ease.” In my words, that translates to a fireplace, casual and/or comfortable seating arrangements like couches or comfy chairs, and a warm drink with alcohol optional…

Chicago is one of the best cities for self-employed individuals and entrepreneurs. Going off on my own almost four years ago now, I’ve had the chance to get to know the city in a different way. It became my office playground like many other people who are in similar career paths and work environments. I’ve explored different neighborhoods and found a few favorite spots to return to and a few spots that are better for casual coffees with friends. For a productive day “out of the office,” I learned quick that cafes and coffee shops with a strong internet connection are vital. It’s also a perk if they offer real food and not just snacks or pastries as well as plenty of outlets. To meet with colleagues or clients, it’s important to find spots with a lower noise level or at least moderate so you can have a conversation without screaming. Some of the best spots are tucked away in the neighborhoods of Chicago and others are right in the heart of downtown. All it takes is a little exploration to find the right ones!