The fall season came and went in the blink of an eye, and we’re at that time of year where we’re getting ready to prepare for another long Chicago winter. But as we approach Thanksgiving this year, it also signals that the holiday season is just around the corner!
We’re The Ben Lalez Team, and while we’re getting ready to put our snow tires on for winter home showings, we’re also finding ways to make sure we enjoy the most of what Chicago has to offer as 2025 wraps up.
We’ve put together this guide covering some of the best parades, markets, light displays, and events happening around the city. We hope you make the most of your November and December in Chicago!
Parades & City Traditions
Wintrust Magnificent Mile Lights Festival (Nov 22, 2025)
This marks the start of the holiday season in Chicago. This free festival happens on Michigan Avenue (parade runs from Oak Street to Wacker Drive, with activities at Pioneer Court).
During the day, there’s a Lights Festival Lane with a host of family activities. The evening parade features Mickey and Minnie Mouse leading the lighting ceremony for over a million lights on 200 trees along the Magnificent Mile. You’ll get an awesome fireworks ending over the Chicago River around 7:15 pm. For more information, visit the official Magnificent Mile Lights Festival page.
There’s also a sweepstakes you can enter for a family vacation to Walt Disney World Resort! The contest ends on November 24th, so you have to hurry to submit your entry. You can find contest details here. Go, go!
Chicago Thanksgiving Parade (Nov 27, 2025)
The Chicago Thanksgiving parade has been running for nearly 90 years. It begins at Ida B. Wells Drive and proceeds down State Street to Randolph Street, starting at 8:00 am.
You’ll see giant character balloons, marching bands, floats, dance teams, horses, and even Santa makes an appearance. As always, it will be broadcast live and is one of the biggest Thanksgiving parades in the country. For more information, visit the official Chicago Thanksgiving Parade page.
There’s also still time to become an Individual Sponsor of the parade and become a VIP for only $80. You can check out VIP details here.
City of Chicago Christmas Tree Lighting (Nov 21, 2025)
The tree lighting ceremony takes place at Millennium Park (near Michigan Avenue and Washington Street) on November 21st at 6:00 pm. This year’s tree is a 66-foot Norway spruce.
The preshow starts at 5:00 pm, with the official light switch happening at 6:25 pm (we recommend you come super early). The tree will stay lit every night until January 11, 2026, so make sure to pop by and get your annual photo with the family! For more information, visit the official City of Chicago Christmas Tree page.
CTA Holiday Train & Bus (Late Nov – Dec 2025)
For over 30 years, the CTA Holiday Train has been running for the holiday season, covered in thousands of lights and decorations and with Santa on an open-air sleigh car.
It runs on all the ‘L’ lines on scheduled days throughout the season. You can ride it with your regular CTA fare. They also run a decorated Holiday Bus on some routes as well.
Make sure to check the CTA website for the 2025 schedule because they update it closer to the dates. For more information, visit the official CTA Holiday Train page.
You can also click here to see a YouTube video of the CTA Holiday Train.
Chicagoland Toys for Tots Motorcycle Parade (Dec 7, 2025)
This might be the world’s largest motorcycle parade, when thousands of bikers ride up Western Avenue carrying toy donations. Now in it’s 48th year, the parade starts on the South Side and heads north, collecting toys along the 20+ mile route. It’s a pretty unique Chicago thing. For more information, visit the official Chicagoland Toys for Tots page.
If you’re interested in donating toys (or money) this year, scan the QR code below.
Holiday Markets
Christkindlmarket 2025 (Late Nov – Late Dec, 2025)
Christkindlmarket is modelled after traditional German holiday markets, where you’ll find vendors selling handmade ornaments, toys, nutcrackers, and other unique gifts. You can get German food like bratwurst and strudel, plus hot drinks in souvenir mugs.
There will be three locations happening this year, so make sure to check the individual dates and times for each location:
Chicago
Daley Plaza, 50 W Washington Street
November 21 – December 24
Sunday through Thursday: 11:00 am – 8:00 pm
Friday through Saturday: 11:00 am – 9:00 pm
Special Opening Hours:
Preview Event (November 20): 5:00 pm – 9:00 pm
Thanksgiving (November 27): 11:00 am – 4:00 pm
Christmas Eve (December 24): 11:00 am – 4:00 pm
Aurora
RiverEdge Park, 360 N. Broadway, Aurora
Thursday: 11:00 am – 7:00 pm
Friday through Saturday: 11:00 am – 9:00 pm
Sunday: 11:00 am – 6:00 pm
Special Opening Hours:
Thanksgiving (November 27): 11:00 am – 4:00 pm
December 22 through December 23: 11:00 am – 7:00 pm
Christmas Eve (December 24): 11:00 am – 4:00 pm
Wrigleyville
Gallagher Way, 3635 N Clark St
November 23 – December 31
Monday through Thursday: 3:00 pm – 9:00 pm
Friday through Saturday: 11:00 am – 10:00 pm
Sunday: 11:00 am – 7:00 pm
Special Opening Hours:
Thanksgiving (November 27): 11:00 am – 4:00 pm
December 22 through December 23: 11:00 am – 9:00 pm
Christmas Eve (December 24): 11:00 am – 4:00 pm
Christmas Day (December 25): CLOSED
December 29 through December 30: 11:00 am – 9:00 pm
New Year’s Eve (December 31): 11:00 am – 4:00 pm
Admission is free, and for more information, visit the official Christkindlmarket Chicago page.
Winterland at Gallagher Way (Nov 23 – Dec 31, 2025)
Winterland is an event held around Wrigley Field at Gallagher Way, featuring the Christkindlmarket, the Gallagher Ice Rink (which remains open through February 15), a holiday train ride that loops around Wrigley Field’s concourse, and Santa’s Workshop for photos.
Entry to the grounds and market is free, but there is a cost for skating and rides. They’re doing a tree lighting on December 5 and some outdoor holiday movie nights in December. For more information, visit the official Winterland at Gallagher Way page.
Navy Pier’s Winter WonderFest (Dec 5, 2025 – Jan 4, 2026)
Winter WonderFest is back after taking some time off. It’s an indoor carnival happening at Navy Pier’s Festival Hall, featuring an ice skating rink, carnival rides, giant slides, a 42-foot holiday tree, and live entertainment.
It’s open daily at 10:00 am, except on December 25. You will need to buy tickets to enjoy the event, but they include unlimited rides and even a ride on the Centennial Ferris Wheel. For more information, visit the official Navy Pier Winter WonderFest page.
Click here to buy tickets ahead of time.
One of a Kind Holiday Show & Sale (Dec 4-7, 2025)
Over 600 artists and makers set up stalls at the Merchandise Mart for only 4 days, selling handmade gifts, art, jewelry, home decor, furniture, fashion, food, and much more.
They often have meet-the-maker talks and craft demos, so if you’re looking for unique gifts, this is a good place to check out. For more information, visit the official One of a Kind Show page.
Holiday Light Displays
ZooLights (Nov 21, 2025 – Jan 4, 2026)
Every holiday season, the zoo gets decorated with more than a million LED lights, and you can walk through tunnel lights and see musical light shows. There will be rides, photos with Santa, live ice carving, wandering carolers, and much more.
Most nights are free entry, though they might require free reservations on busy evenings. Some special nights will require tickets, so make sure to check online before you head out. For more information, visit the official Lincoln Park Zoo ZooLights page.
Lightscape (Nov 14, 2025 – Jan 4, 2026)
Lightscape is a one-mile outdoor trail through the Botanic Garden that has immersive light art installations and synchronized music. We’re talking tunnels of lights, glowing displays, and fire features.
This one usually sells out, so get tickets ahead of time if you’re planning to go. For more information, visit the official Chicago Botanic Garden Lightscape page.
There is also an option to book a private event at Lightscape this year, or book a package if you’re interested in proposing to your loved one under the lights. Make sure to check their page for these packages!
Illumination (Nov 15, 2025 – Jan 3, 2026)
This event is about a 30-minute drive from the city in Morton Arboretum, Lisle. 50 acres of trees will be lit up with color-changing displays and music. There are interactive segments where you can sing to make the trees “dance,” plus bonfire areas to warm up.
This year, they added expanded light tunnels and a Holiday Illumination maze. Make sure to dress warm because you’ll be outside walking for a while. For more information, visit the official Morton Arboretum Illumination page.
Holiday Magic (Select nights Nov 21 – Dec 31, 2025)
This event at Brookfield Zoo has been running for over 40 years, and this time they’ve got over 3.5 million lights ready. There will be illuminated animal exhibits, a 600-foot Tunnel of Lights, a giant light maze, holiday laser shows, and of course, a chance to meet Santa.
Some people sing carols to the animals, which we always find amusing. For more information, visit the official Brookfield Zoo Holiday Magic page.
Quick note: Holiday Magic and North Gate parking are FREE for Members. There is a fee and advanced tickets are required for South Gate entry.
Performances & Cultural Events
Joffrey Ballet’s The Nutcracker (Dec 5-28, 2025)
The Joffrey’s version of The Nutcracker is set at the 1893 World’s Fair in Chicago, and is showing at the Lyric Opera House. There are multiple shows each week through the end of December.
The Chicago Philharmonic performs Tchaikovsky’s music live, and it’s a big production, with toy soldiers, a growing Christmas tree, and so much more. For more information, visit the official Joffrey Ballet Nutcracker page.
Goodman Theatre’s A Christmas Carol (Nov 15 – Dec 31, 2025)
The Goodman has been doing A Christmas Carol for nearly 50 years. Shows run every day, with both evening and matinee shows through New Year’s Eve. If you’ve never seen it, it’s worth going at least once. For more information, visit the official Goodman Theatre Christmas Carol page.
Christmas Around the World at Museum of Science and Industry (Now until Jan 5, 2026)
For something really cool, head out to the MSI to check out over 50 decorated trees representing different cultures and their holiday traditions. There’s a 45-foot Grand Tree surrounded by displays from Polish, Filipino, Mexican, and other ethnic communities showing how they celebrate Christmas, Hanukkah, Kwanzaa, Diwali, and more.
Live cultural performances and choir concerts take place on weekends. It’s all included with museum admission. For more information, visit the official MSI page.
St. Lucia Festival of Lights (Dec 13, 2025)
The St. Lucia Day Festival starts its candlelit procession at the Swedish American Museum at 4:45 pm and will stop at the Christmas tree at Catalpa Avenue around 5:00 pm for a program.
Afterwards, there’s a celebration at Ebenezer Lutheran Church at 7:00 pm. It’s free and family-friendly. You can find the event details here.
Kwanzaa Celebration (Dec 26, 2025)
The Bronzeville Children’s Museum marks the first day of Kwanzaa with a family celebration. There will be Kwanzaa storytelling, dancers or drummers, candle-lighting of the kinara, and crafts for kids.
It’s a good way to learn about the seven principles of Kwanzaa and celebrate African American heritage. For more information, click on this link.
New Year’s Eve on Navy Pier (Dec 31, 2025)
Once again, the annual New Year’s Eve fireworks display will be happening from Navy Pier. Dress very warm because it’ll be cold and windy by the water. Navy Pier might have ticketed events inside, so check their website for details.
For more information, visit the official Navy Pier page.
Dick Clark’s New Year’s Rockin’ Eve’ (Dec 31, 2025)
For the first time in its 55-year history, Dick Clark’s New Year’s Rockin’ Eve will broadcast live from Chicago with its own Central Time zone midnight countdown. The show airs on ABC starting at 7:00 pm on December 31st. Chicago will join Times Square and Puerto Rico as one of the countdown locations.
The broadcast will feature a new Chicago host (not yet announced), live musical performances, and on-the-ground reporting throughout the evening.
This is Chicago’s first time being part of the national broadcast, and we’re pretty excited! For more information, visit ABC7 Chicago or check Dick Clark’s New Year’s Rockin’ Eve updates.
Wrapping Things Up
As we head to the tail end of 2025 and into the winter months, we know that summer feels so far away. But there are plenty of things to do that can make the winter enjoyable. Between the markets, light festivals, and performances, you’ve got lots of options for getting out of the house (even when it’s freezing).
If you’re thinking about making a move over the next few months and want to talk about which neighborhoods might be best for you, we’d be happy to talk! We know the city better than anybody, and can help you see parts of Chicago you might not have even discovered yet. Give us a shout, and we’ll be talking to you soon!
