Did you know December is only a few weeks away? We may be waiting for Halloween and Thanksgiving, but we’ve already got the holidays on the brain. And we’re not alone. Just touring through our favorite shops in Old Town and we’ve spotted signs of the merry season ahead.

Old Town is a historic borough in the heart of the Windy City, featuring beautiful architecture that becomes a winter wonderland during the cold months. Whether you want to immerse yourself in the award-winning culinary scene, enjoy the cities charming holiday attractions, or just cozy up with coffee and take in the whimsical views, Old Town has precisely what you're looking for. It’s impossible to experience everything in one weekend, but our get-away agenda highlights the must see's for a first-time visit.

City of Chicago Christmas Tree Lighting Ceremony



Make your way over to Millennium Park to experience the annual Chicago Christmas Tree Lighting Ceremony on November 16th. You can expect the best in holiday music, an appearance from the mayor and all your favorite holiday treats.

The Robey



This neighborhood café serves up Chef Kevin McAllister’s Modern American fare along with eccentric cocktails. Enjoy the warmth that comes over you while you sip on Grandma Charlotte's Secret Recipe. A favorite holiday cocktail made with graham cracker-infused bourbon, garnished with pumpkin syrup, and topped with a gooey toasted marshmallow.

La Colombe Coffee



Who doesn't love to cozy up with a hazelnut latte during the holiday season? With exposed brick walls (great for impromptu selfies) and beautiful street views, La Colombe Coffee is the perfect place to escape the cold and enjoy an elevated coffee experience.




A Chicago Christmas isn't complete without stopping by this giant outdoor market located only 10-minutes from Old Town. You'll find every whimsical Christmas gift you could think of from nutcrackers, snow globes, and tree ornaments. Inspired by similar seasonal tradition in Nuremberg, Germany. You won't want to pass up trying a traditional German sausage paired with some hot spiced wine.

Steppenwolf Theatre



The Steppenwolf Theatre is a wondrous hub of dramatic productions. With over 16 plays and nearly 700 performances, readings and other events every year on their three stages, there is something for everyone. Tickets start at $60 and upward, You can also opt for one of their memberships, which gives you discounted prices and perks.

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