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  • Writer's pictureCatherine Joy

8 Ways to Celebrate the Holidays in The Windy City

Those who live in (or know anything about) Chicago, know that winter-time can be absolutely brutal in the Windy City. It’s cold, gray, snowy, and can be just downright miserable during the colder months of the year. Luckily, it isn’t all doom and gloom during the month of December though! The great thing about a big city like Chicago is that there are tons of fun, festive things going on when temps start to get cold again. For the past 5 or 6 years, I always try to come down to the city during the holiday season to partake in some of my favorite Chicago Christmas events! Read on to see some of my favorite ways to celebrate the holiday season in The Windy City!

8 Ways to Celebrate the Holidays in Chicago

  1. Christkindlmarket - located at the Daley Plaza! Participate in the German Christmas celebration by grabbing a warm mug of mulled wine in a souvenir mug, munching on some delicious traditional German food, or purchasing beautifully hand-crafted Christmas ornaments in the pop-up shops!

  2. Lincoln Park Zoo Lights - Be mesmerized by their gorgeous holiday lights display, and maybe even spot a few animals while you’re at it!

  3. Ice skating at The Peninsula or Millenium Park - Is it even winter in the Midwest without ice skating rinks? Visit the incredible Peninsula Hotel’s “Sky Rink” or rent a pair of skates in Millenium Park (Also, check out the giant, beautiful Christmas tree in Millenium Park!)

  4. Winter WonderFest at Navy Pier - Navy Pier is the perfect place to go during the holiday season to experience games, rides, holiday decor and attractions all in one place! Tickets can be purchased ahead of time here.

  5. Shopping! - There is no better place than the city for Christmas shopping! Walk down Michigan Avenue to find something for everyone on your list! And while you’re at it...

  6. Stroll down Michigan Avenue at night - The streets of Chicago are all aglow with Christmas lights during the holiday season, and it’s a delight to see!

  7. Santa Baby Bar - Deuces Bar in Wrigleyville completely transforms itself into a Christmas Splendor for the whole month of December! Check that out to be mesmerized by Christmas decor, songs, and to enjoy a pint of your favorite adult beverage out of a Santa boot!

  8. Eve of the Eve - The perfect end to the holiday season! John and I did this last year, and we are most likely doing it again this year! Avoid the New Years Eve crowds and high cover priced on December 30th (the night before New Years Eve) by attending Eve of the Eve, an early New Years celebration full of dancing, live music, hors d'oeuvres, and an open bar that benefits a local scholarship program for students from low-income families!

Have you ever been to Chicago in the winter time? Let me know in the comments!

As always, thanks for reading!

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