10 Things to do During Chicago's Holiday Season!

Posted by Ted Guarnero admin on Thursday, November 10th, 2011 at 1:30pm.

10 Best 2011 Holiday Events in Chicago!

I am hoping that my recent blog about the Magnificent Mile Lights Festival generated a smidgen of holiday spirit, as I realize we’re still barely into November and the thought of Christmas, Hanukkah and New Year’s may be a bit overwhelming for many of us right now. But despite where we’re at on the calendar, The Magnificent Mile Lights Fest is still only one week away [roughly] and I thought this was the perfect time to generate a list of fun-filled activities happening on November 19th and throughout this year’s holiday season in downtown Chicago. So without further ado, I present to my readers 10 things to do during this year’s celebration:

1)      November 1st-December 31st: Winter Wonderland  @ the John Hancock Observatory

  • Believe it or not, this year is the 40th anniversary of holiday festivities at the John Hancock Observatory. Santa Claus will stop in at the JHO every weekend from 12-4pm and various dates throughout the holiday season offer different fun-filled activities for kids of all ages. Check out the JHO web site for more details!

2)      November 5th : Macy’s Great Tree Lighting & Holiday Windows

  • Although you may have already missed the kickoff to Macy’s fabulous holiday window displays (oops!), the 45-foot Great Tree with 10,000 LED sparkling lights and 1,200 ornaments and this year’s window display, themed “Yes Virginia, there is a Santa Claus, will be up all season!  

3)      November 17th-January 8th:  Museum of Science & IndustryChristmas Around the World & Holidays of Light”

  • On display will be more than 50 trees, beautifully decorated by members of Chicago’s ethnic communities to represent global cultures during the holiday season. As you stroll through the Museum halls, sporadic “falling snow” allows for the ultimate holiday experience!

4)      November 19th: Live concerts on the BMO Harris Bank Stage 

  • 11am: Justin Roberts and the Not Ready for Naptime Players
  • 12pm: The Never Land Pirate Band
  •   1pm: Radio Disney AM 1300 Road Crew, Radio Disney’s Next Big Thing Artists

5)      November 19th – January 1st: Michigan Avenue Holiday Lights

  • Who doesn’t enjoy walking down Michigan Avenue and enjoying the ultra-urban atmosphere of the Streeterville neighborhood in downtown Chicago? Well, during the holiday season, Chicago’s most recognized thoroughfare displays breathtaking light displays, with some of the city’s best shopping options along the way so you can get some of that dreaded holiday shopping out of the way!

6)      November 24th: Chicago’s Thanksgiving Day Parade

  • Kicking off at 8:30am, the Chicago Thanksgiving Day Parade will boast awesome inflatable, beautiful floats, marching bands from around the Midwest, dancing groups, and more! The parade runs on State Street from Congress Parkway to Randolph Street. Get there early to get a great spot!

7)      November 24th-December24th (Fridays & Saturdays): Christkindlmarket Chicago

  • This year marks the 16th year that the open-air, German-style market will display a wide-variety of handmade ornaments, holiday accessories, clothing and gifts. Over 50 vendors are expected to participate and delicious German-inspired food and drinks that include hot spiced wine, potato pancakes, bratwurst, chocolate desserts and more will also be on hand!

8)      November 25th – December 16th (Friday Evenings): Caroling at Chicago’s Bean

  • Starting at 6:50pm, every Friday evening from November 25th to December 16th, the Chicago Office of Tourism and Culture will showcase various Chicago choral groups and also invites visitors to participate in a holiday sing-along. Now labeled as one of Chicago’s most cherished traditions, participants can also stay warm at the event with complimentary beverages provided by Caribou Coffee! Also, be sure to stop by Millennium Park’s McCormick Tribune Ice Rink while down at the Bean, as this too is also one of the most popular winter destinations in Chicago!

9)      December 16th – January 1st (Open nightly 5-9pm. Free!): Lincoln Park Zoolights

  • Along with putting on an unbelievable lights display, don’t forget to check out all the great things to do at the Lincoln Park Zoo during the holiday season, which includes visits with Santa, animals from around the world, live ice carving, and holiday arts and crafts!

10)   Dates to be released at a later Date: CTA Holiday Train

  • Every year, the Chicago Transit Authority decorates a CTA “L” train with an array of lights and runs it down each line at pre-determined dates. On board will be Santa and his elves, passing out candy canes and holiday cheer to all the passengers on-board. The open-air flat car holds Santa’s seat and reindeer, making this an awesome spectacle for kids as the train pulls up to each station! 


Ted Guarnero, REALTOR® is a full-time real estate agent with over 1000 homes sold and $400 million in sales.  Working with Compass real estate offering professional and effective real estate services to help you succeed in the local real estate market. Visit www.seeChicagorealestate.com for information on downtown Chicago real estate and to get in touch with an expert in the Chicago real estate market. Before you hire your next Realtor call Ted Guarnero 855-See-Chicago, it's on the House !


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