THIS WEEKEND IN CHICAGO – Welcome to Our Holiday Season!

This weekend is the “official” kick-off to our Holiday Season here in Chicago and as usual there is no shortage of things to do to get into the festive spirit! Let’s get started!!
Are you ready to celebrate and kick off the holiday season with us? Then come join us at the 34th annual Wintrust Magnificent Mile Lights Festival® this Saturday for a fun-filled day of holiday activities on the Magnificent Mile (625 N. Michigan Ave.) on the Near North Side. This beloved tradition kicks off at 11:00 a.m. with Lights Festival Lane at Pioneer Court (401 N. Michigan Ave.). This festive outdoor celebration offers a variety of family-friendly activities which include complimentary Wintrust Photos with Santa, cheesecake decorating with Eli’s Cheesecake, and more. Plus, there’s special holiday appearances of ‘Twas the Night Before… by Cirque du Soleil from The Chicago Theatre at 12:30 p.m., 1:45 p.m., and 2:45p.m. Then beginning at 5:30 p.m. the spectacular Magnificent Mile Parade heads down North Michigan Avenue featuring Mickey Mouse and Minnie Mouse of Walt Disney World® Resort as the Grand Marshals along with fabulous floats with other beloved friends from the Walt Disney World® Resort, giant helium balloons, marching bands from across the country, musical celebrities, one million shimmering lights illuminating the 200+ trees on The Magnificent Mile, and yes, Santa Claus himself. The evening ends with the Wintrust Fireworks Spectacular. Let the Holidays begin!
Another of Chicago’s favorite holiday traditions is back and brighter than ever with the Lincoln Park ZooLights now through January 4, 2026, at Lincoln Park Zoo (2001 N. Clark St.) in the Lincoln Park neighborhood. With over 3 million lights you will step into a world of sparkle and shine that also features hundreds of nostalgic LED displays, and festive experiences such as rides and attractions (tickets required), photos with Santa through December 23, live ice carving on Friday and Saturday nights, strolling carolers on Sundays through December 21, indoor self-guided tours, and more that capture the magic of the season!
This holiday season set sail on the Chicago River with Sleigh Rides with Santa! every Friday, Saturday, and Sunday through December 21 at the DuSable Harbor (200 N. Breakwater Access) in the heart of Downtown Chicago. This budget-friendly outing not only offers family-friendly fun with holiday vibes and Santa Claus, but it also offers a magical way to see Chicago’s winter skyline for an unforgettable experience that is filled with festive cheer and fun. Why not make this holiday season one to remember!
The Holiday Magic of the season is real at the Museum of Ice Cream’s Pinkmas this Saturday (10 a.m.-7 p.m.) through January 19, 2026, located at 435 North Michigan Avenue, Suite G, in the Streeterville neighborhood. The Museum has been transformed into a breathtaking forest of pink as you wander through a larger-than-life snow globe, uncover dazzling surprises, snap festive photos, indulge in all-new festive ice cream creations, and more. You won’t find this original immersive holiday magic anywhere else, so come step into the sweetest holiday celebration of the season!
It’s Turkey Time! Thursday, November 27 brings us Thanksgiving Day, and the following events before we overstuff ourselves with turkey and all the other trimmings.
One of Chicago’s beloved Thanksgiving traditions is the Turkey Trot Chicago taking place at the North Pond in Lincoln Park (2610 N. Cannon Dr.) in the Lincoln Park neighborhood. Runners can choose between a 5K or 8K course and are usually dressed as pilgrims, poultry, superheroes, and the like but it’s not required. There’s even a Kid’s Run so they too can burn off some of their energy. Afterwards, celebrate your finish at the Turkey Trot Tailgate with delicious fall treats, live music, and fun activities for everyone. It’s a perfect way to start your Thanksgiving Day!
Another of Chicago’s beloved Thanksgiving traditions is the Thanksgiving Parade taking place on State Street from Ida B. Wells Drive to Randolph Street in The Loop from 8:00 a.m. to 11:00 a.m. This local tradition for almost 90 years features live entertainment that includes the country’s top marching bands, live music, festive floats, acrobats, equestrians, cultural performances, celebrity hosts, larger-than-life helium balloons, and more. Gobble, Gobble!
Have a Great Weekend and a Happy Thanksgiving!
Sue Moss and Dean’s Team Chicago









