33 Best Things to do in Chicago in Winter

Chicago in winter gets a bad rap, but it’s a truly magical time to visit the Windy City.

Winter in Chicago may be cold and windy, but it’s also magical. The city comes alive with twinkling lights, festive markets, and cozy hideaways, transforming the harsh weather into part of the charm.

As a Chicago area resident since 2001, thirteen of those years in the Windy City itself, I can verify that the winter season in northern Illinois can be a bit testy.

We’ll go stretches of days, and sometimes weeks, without sight of the sun and locals frequently wonder why they live in a place where it hurts to breathe.

We’ll get a foot of snow in a day, and then when we think winter’s gone, she’ll come back for one last hurrah. That wind can be brutal, stinging your face like an acupuncturist gone haywire.

And yet…

Chicago winters are a magical time of the year. The city unfurls all its finery, with decorated storefronts, streets draped with thousands and millions of lights, ice skating, and festivals.

There’s even a real, live holiday evergreen tree culled from a local’s land that towers over Michigan Avenue.

From an authentic German market to an indoor winter wonderland, to free days at the city’s world class…