The Holidays in Chicago are the most wonderful time of the year!

Updated October 2024

Condé Nast Traveler named Chicago the best American big city to visit. Not only did they rave about Chicago, but they also hailed it as one of the ultimate holiday season destinations – and we’re wholeheartedly on board with that! So, without further ado, here’s our guide to Christmas in Chicago!

Bursting with boundless energy, a Chicago holiday season is unlike any other. Here are some of our cherished Chicago holiday events and traditions! With its vast array of top-notch restaurants and bars, spectacular museums, shopping havens, and exhilarating events, your Christmas in Chicago will surely help you make great memories. Thanksgiving in Chicago is fabulous too! 

Christkindlmarkt are always a magical experience you don’t want to miss!

The European Christmas Market in Chicago

Chicago has a European-style Christmas market! We think the Christmas market is a must visit for any Chicago visitor. Officially called Christkindlmarkt, the original is on Daly Plaza, although two other locations have been added as well. Modeled after the European Christmas markets, it has vendors from Germany. Looking for Krampus items? You will find them here! 

And not only can you buy great holiday gifts and ornaments, but it’s also a fun place for a drink or a snack. You will find candies, cookies, pretzels, potato pancakes, sausages, and more.  You must try the gluhwein, a mulled wine you can get in an adorable souvenir mug.

Once you Have enjoyed the Market, it’s only a couple of blocks to Macy’s where you can check out the famous holiday tradition, the Macy’s holiday window displays.  

Moose

Chicago Christmas Shows

Of course, you can see A Christmas Carol and the Nutcracker, but there is also Christmas with C.S. Lewis and plenty of other holiday shows.

And if you have been wanting to see Hamilton, it is back through January 28.

If the symphony is more your speed, make sure to check out the perennial favorite at the Chicago Symphony Orchestra.

Christmas Parades

Chicago has terrific parades. We love the Magnificent Mile Lights Festival on November 23th, because they light the magical lights on Michigan Avenue as the parade proceeds south; but the Thanksgiving Day parade is awesome too.  

Always on the first Sunday in December, make sure you don’t miss the Chicagoland Toys for Tots Motorcycle Parade, which helps do fundraising for the Toys for Tots charity which helps bring joy into the lives of underprivileged children across the country. Motorcyclists are encouraged to join, with the entry fee just being an unwrapped toy donation. 

Less a parade, but no less spectacular, check out the Morton Arboretum’s Illumination display. 

New Year’s Eve

Finally, New Year’s Eve always brings great fireworks off Navy Pier. These fireworks can be enjoyed by anyone with a clear view of the pier, but you can get up close and personal on the pier itself. 

If you’re the party type, a lot of Chicago hotels hold New Year’s parties, but perhaps the biggest, most famous of them is the one held at The Drake Hotel, just off Michigan Avenue.

Chicago’s many bars and restaurants also will be hosting their own parties. There are so many choices, you’ll have a hard time just choosing one! 

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