The best places to explore this holiday season in Chicago

It’s that time of year: Break out the ornaments, put the menorah in the window, throw some flannel sheets on the bed. But don’t miss out on what Chicago has to offer, there’s plenty of charm outside your cozy home. The winter season brings out the magic in each neighborhood.

In this choose-your-own-adventure guide, we’ll point you to the best places to liven up these dark winter days. Shop local holiday markets for handmade gifts, discover the best Christmas lights in the city, and explore a new ice skating rink.

Visit the essential places in Chicago

Our seasonal city guide highlights the best architecture, historic sites, and other places you don’t want to miss in Chicago. We’ve also got a guide to the city for people traveling with kids. These guides will come in handy, especially if you’ve got relatives visiting for the holiday season. Need somewhere to go Christmas Eve? The Garfield Park Conservatory is open through the holidays, and they’ve got a vibrant flower show with pink poinsettias and evergreen trees. Families can head to Gallagher Way near Wrigley Field for professional ice skating demos, wreath-making workshops, and a mini holiday market.

Shop local

There are a ton of pop-up holiday markets and local shops are stocking the shelves with the best of the best. Whether you’re looking for design-forward kid-friendly kitchenware, throw blankets pretty enough to hang as art, or the perfect tool kit for a year-round cyclist—we’ve got you covered with the Chicago gift guide. Our curated list of essential furniture stores might help you find the perfect new couch and these vintage stores will help get your holiday glassware in line. But, if you’re seeking a one-of-a-kind shopping experience check out our list of holiday markets for items like vintage ornaments, hand-dyed textiles, or art prints.

See holiday lights

ZooLights in Lincoln Park is undoubtedly the city’s most popular holiday light display. It features over a million LEDs, inflatable snow globes, ice sculptors, and lighted tunnels. But have you seen the Logan Square Christmas House? There’s something to be said for homeowners who put on fantastical holiday decor displays—it’s truly awe-inspiring. Here’s where to find the city’s best lights.

Ride the holiday train

Whether you’re a kid or not, there’s some magic in seeing Santa roll up on the CTA’s holiday train. It’s become so popular that there’s now a holiday bus dressed up like a reindeer and a six-car Elves’ Workshop train that follows Santa. A complete schedule can be found on the CTA website, along with what stops will have time for photo sessions. Do you know what sparked this tradition? A simple holiday message on the front of a train in 1992.

Glide around the best skating rinks

What better way to embrace the cold than to take a trip to the city’s best skating rinks? Aside from the Maggie Daley Skating Ribbon, we love the Park District’s rinks in Warren Park, McKinley Park, and the Midway Plaisance. A bit more luxurious is the SkyRink atop the Peninsula Hotel features a faux ski chalet and skyscraper views. Too chilly outside? Head to Navy Pier’s Winter Wonderfest, which boasts much more than an indoor rink. There are ice peak climbing walls, giant inflatable slides, spinning teacup rides, train rides, and a faux snow tubing hill.