Wednesday, June 25, 2025

Chicago’s Winter Wonderland: A Local’s Guide To Holiday Season Events

Plan Your Holiday Season in Chicago

It’s cold out, the wind is picking up, and here’s another four months of gray and freezing weather before spring. I need a full calendar of fun to keep me going in the winter, and thankfully Chicago provides! I’ve put together a diverse list of local events that I’ll be attending to elevate my holiday season and keep me joyful in the cold and wind. 

Here are a few of our holiday recommendations if you are in the Chicagoland area this holiday season. 

Chicago Botanic Garden – Lightscape

Dates: 11.11.24-1.08.25 

I go every year and never regret it. If you want to experience “Walking in a Winter Wonderland” even if there’s no snow on the ground, this is it. It’s a magical experience of artists making crazy lightscapes throughout the Botanic Gardens. Kids go crazy over the changing lights and cool art -it looks like AI but it’s real life. It’s a bit of a drive, but well worth it. Buy tickets here.

Chicago's Winter Wonderland Guide
Photo Credit: Caitlin Bower/The Travel Addict

Winter Flower Show – Garfield Park Conservatory

Dates: 11.27.24-1.08.24

The entrance fee is a suggested donation (for a great cause!!), but make your reservations in advance so you can walk right in when you get there! The Garfield Park Conservatory is without a doubt my favorite spot to hang out in the  winter. I can feel like I’m in a steamy Jurassic Era jungle or an arid desert, even when the wind chill’s making it -10 outside. Reserve your spot for Garfield Park Conservatory

Photo Credit: Caitlin Bower/The Travel Addict

Art Institute 

Open Daily

This is one of their free days for residents, and seeing beautiful art always lifts my spirits. They also always do it up with the garlands around the iconic front lions and interior holiday decor, which I love to see. Make Free Ticket Reservations Here

Chicago's Winter Wonderland Guide
Photo Credit: Pexels

Andrew Bird – Gezelligheid

Dates: December 9-13, 2024

As an older millennial who loves whistling, I’ve always been a huge Andrew Bird fan – I’ve seen him at Ravinia and many other venues, but I’ve heard this is a truly special experience. This has been an ongoing holiday tradition since 2009 of warm, comforting music on cold evenings at Chicago’s Fourth Presbyterian Church. “Gezelligheid” is the Dutch word for cozy, which is what the concert aims to be. This will also be live streamed if you can’t make it out. Link to Andrew Bird Tickets

Eat Raclette – Christkindlmarket 

Dates: 11.22.24-12.24.24 

I don’t think this needs much explanation. Go for the mulled wine and the cute ornaments, stay for the Raclette sandwiches and hot chocolate. It’s so cute and the melted cheesy raclette is to die for!! Just a reminder, if you already have one of the annual mugs, you probably don’t need 5 more. 

Chicago's Winter Wonderland Guide
Photo Credit: Caitlin Bower/The Travel Addict

Cobra Lounge – A Volpe Family Christmas

Date:  12.14.24 

This is my unhinged pick – I went last year and it was wild! If you are at all a fan of the St. Louis alt-rock band Ludo, this is an absolute must. Party family party, part role-playing game, part caroling, and part intimate concert, this is one of the weirdest and most delightful Christmas events I’ve ever experienced. The party is  located in the back room of the Cobra Lounge, so definitely a bar, but the bar is not inside the room. With the caroling, children running around and holiday vibes, it’s easy to avoid alcohol. Tickets for A Volpe Family Christmas

Chicago's Winter Wonderland Guide
Photo Credit: Caitlin Bower/The Travel Addict

Annual Winter Solstice Concert Series – Links Hall 

Date: 12.21.24-12.23.24 

I attended this last year and loved it. Hamid Drake and Michael Durang, two incredible musicians (primarily drummers) begin at the first touch of dawn (get there in time to enter at 6am and bring a pillow or blanket, though there are chairs available as well.) They play through until morning has fully dawned, and the ritual is so beautiful and a perfect way to greet the new year and shorter nights. Link to Solstice Tickets

No Wasted Time: Largest Alcohol Free New Years Eve Party

Date: 12.31.24

Begin as you mean to go on! I’ve been sober-curious for a few years, and alcohol free since late July of this year, but I love a good New Year’s Eve Party. I’ve never been to a sober NYE party, but I’m excited to drink fancy mocktails and dance into the new years! NYE Party Tix

No matter what your interests, Chicago has got something for everyone the holiday season so grab a coat and get out there and enjoy the festivities.

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