Chicago is a city that thrives in transition. As November melts into December, neighborhoods buzz with events that straddle the last whispers of fall and the sparkle of the holiday season. It’s a time for hearty meals, twinkling lights, and vibrant community spirit. Whether you’re embracing the festive cheer or savoring the lingering autumn vibes, both November and December are pristine in Chicago.
As we reflect on the many months gone by, year after year we collectively wonder: What is it about this time of year that draws us closer to each other? Whatever the reason, winter begs for time to slow down and asks us to savor and seek out the extraordinary moments hidden in the city’s corners. Join me as we explore the events that make this season in Chicago unforgettable, and perhaps inspire us to see the world—and each other—a little differently…
Chicago Thanksgiving Parade
Location: State Street, From Ida B. Wells Drive to Randolph, Downtown Chicago
Date: Thursday, November 28, 2024
Kick off the holiday season with the iconic McDonald’s Thanksgiving Parade, a time-honored tradition that’s been bringing holiday cheer to Chicago for over 90 years. This annual parade is one of the largest in the country, featuring giant balloons, colorful floats, marching bands, and performances from local artists. This year, expect even more extravagant displays and a festive atmosphere to get you in the holiday spirit. It’s a fun event for all ages, and if you’re in the mood for an early breakfast, grab a cup of coffee and a warm pastry from one of the nearby cafés to enjoy as you watch.
Thanksgiving Dinner Cruises on Lake Michigan
Location: Navy Pier
Date: Thursday, November 28, 2024
For a unique Thanksgiving experience, consider booking a Thanksgiving Day Dinner Cruise on Lake Michigan. Set sail with a picturesque view of Chicago’s skyline while indulging in a delicious three-course holiday meal. The cruise typically includes a buffet featuring turkey, stuffing, mashed potatoes, and all the festive fixings, paired with stunning views of the lake and the city. It’s a memorable way to spend the holiday with family or friends, especially if you’re looking for a different way to celebrate Thanksgiving.
Christkindlmarket
Location: Daley Plaza
Date: November 22 - December 24, 2024
Although technically more of a holiday tradition than a Thanksgiving event, the Christkindlmarket is a must-visit as soon as the holiday season hits. This German-style outdoor market brings festive magic to Daley Plaza with twinkling lights, charming wooden stalls, and delicious food and drink. Sip on mulled wine, sample gingerbread cookies, and shop for handcrafted gifts and ornaments. It’s a great way to start your holiday shopping while soaking in the festive atmosphere. The Christkindlmarket is perfect for families, couples, or anyone who loves the charm of a European holiday market.
Ice Skating at Maggie Daley Park
Location: Maggie Daley Park, 337 E. Randolph St.
Date: November 2024 - February 2025
When the weather turns colder, Maggie Daley Park becomes the city's go-to destination for ice skating. The rink, set against the breathtaking backdrop of the Chicago skyline, is a fun and festive spot to enjoy the winter chill. Whether you’re a seasoned skater or a first-timer, the rink offers rentals and skating lessons, plus a cozy spot to warm up with a hot chocolate.
A Christmas Carol at the Goodman Theatre
Location: Goodman Theatre, 170 N. Dearborn St.
Date: November 16 - December 30, 2024
For those looking to experience the spirit of the season through theater, A Christmas Carol at the Goodman Theatre is a Chicago tradition. This holiday production has been enchanting audiences for decades, with its charming story of Ebenezer Scrooge’s transformation into a kinder, more compassionate man. The talented cast, beautiful set design, and live music create an atmosphere of warmth and holiday cheer that’s perfect for families and theater lovers alike.
Michigan Avenue’s Magnificent Mile Lights Festival
Location: Michigan Avenue
Date: November 23, 2024
If you’re looking to shop for the holidays while soaking in the festive atmosphere, the Magnificent Mile Lights Festival is a must-see. The holiday shopping season kicks off with a grand parade along Michigan Avenue, where the famous trees lining the street are lit up in a dazzling display of lights. The parade includes performances from popular artists, marching bands, and, of course, a visit from Santa himself.
State Street’s Holiday Window Displays
Location: State Street, Downtown Chicago
Date: November - December 2024
Another iconic holiday tradition in Chicago is the stunning holiday window displays along State Street. The windows of department stores like Macy’s (formerly the treasured Marshall Field’s) are transformed into magical winter scenes, filled with festive decorations and whimsical displays. Window-shopping here is a beloved Chicago pastime, and it’s an ideal activity for families or those looking to snap a few photos. Afterward, explore the nearby shops for unique holiday gifts that you won’t find anywhere else.
Chicago’s Best Holiday Pop-Up Shops
Location: Various locations throughout the city
Date: November - December 2024
The holiday season in Chicago is also home to a variety of pop-up shops that offer unique gifts, handmade items, and one-of-a-kind experiences. From local artisan markets to curated holiday pop-ups featuring everything from vintage clothing to
custom jewelry, there’s something for every taste. Check out Shop The World for handmade goods, or head to the Chicago Artisan Market for a curated collection of local creators. These pop-up events are an excellent way to support local businesses while finding that special gift for someone on your list.
Start the holiday season with a smattering of local cheer. Your heart and mind will thank you for it.
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Catch us back here as we bring you curated and Chicago-based real estate content (with a life coach’s twist). Next up: Confused by the news? Clarity found here: Another Year Over: What 2024 Tells Us About the Year That Was (And What’s Coming Next)
