The holiday season is here and I don’t beat around the bush in claiming that Chicago is the best city in the world to enjoy the holidays. It is just a fact. But if there is anything negative about all of the holiday awesome in our fair city it is that there is so much- how do you possibly know what is happening and when and make plans to do it?!? That’s what I am here for. Below you will find links, dates and details for all sorts of fun Chicago Christmas goodness. Mark your calendars, friends!
Tree Lighting at Daley Plaza: November 25th at 5pm
Thanksgiving Day Parade: November 27 at 8am
Christkindlmart: November 21-December 24 Sunday-Thursday 11am-8pm, Friday-Saturday 11-9pm; this German open-air market is open in the Daley Plaza to satisfy your craving for mulled wine in little boots, ornament shopping and wiener-schnitzel.
Wreathing of the Lions: November 28th at 10am the beloved Lions at the Art Institute get their traditional evergreen wreaths and following the ceremony, families are invited inside the Ryan Center to create their own wreaths, totally free.
BrewLights: December 3rd from 5:30-9pm- $40 will get you a dozen holiday beer samples that you can use to keep warm while checking out the Lights.
Southport Holiday Stroll: December 5th from 5-9pm; free cocktails, shopping, sales, more free cocktails, a sleigh that acts like a bus to transport you up and down Southport (for free!), Victorian carolers and Santa & Mrs. Clause. Such a quaint experience for such a big city.
Ice Skating at The Peninsula: The “Sky Rink” opened last Saturday and sits 4 stories above Christmas-ready Michigan Avenue. Combine that with spice wine and you’ve got my kind of outdoorsy activity. Open Monday through Friday 3-8pm, Saturday 12-9pm and Sunday 12-6pm.
Ice Skating at Millennium Park: Monday-Thursday 12-8pm, Friday 12-10pm and weekends from 10am-10pm
Caroling at Cloudgate: Fridays at 6pm starting on November 28th until December 19th, choirs will lead a community singalong in front of the Bean. Mark this down as the most festive thing you could possibly do. I sang my heart out last year.
30th Annual Music Box Theatre Christmas: December 13-24th, The Music Box Theatre does showings of It’s A Wonderful Life and White Christmas. Sometimes Santa shows up and there’s a group singalong. Gosh, I love a singalong.
Kris Kringle’s Kandy Kane Ball: Festive cocktails for a cause at Joe’s on Weed on December 13th from 9pm-12am. Proceeds benefit Chicago Children’s Charities and don’t forget to bring a toy to donate at the door!
Claymas Christmas: December 21 at 9:30pm- Holiday improv. These guys are hilarious.
CTA Santa Train: November 28- December 23- check the schedule for when this hub of Christmas cheer is on your tracks. It smells like cinnamon, Santa and the reindeer are on a flatbed and the inside is covered in decorative holiday awesome. So, basically, the only time during the year when you actually want to get on the El.
Joffrey Ballet’s “The Nutcracker”: December 5-28; Joffrey is one of the best ballet companies in the world and to see them do The Nutcracker is so special.