Top Holiday Winter Experiences in Chicago

‘Tis the festive season, and Chicagoland is brimming with enchanting events that you won’t want to miss. Whether you’re a city dweller, contemplating a move to the suburbs, or simply eager to explore, the holidays offer a perfect opportunity to immerse yourself in the spirit of diverse communities.

Here are some recommendations for holiday happenings across Chicagoland that promise to delight both locals and visitors. After enjoying these events, take a moment to savor the local flavor by grabbing a bite, exploring nearby shops, or taking a leisurely drive through the neighborhoods.

Cheers to the Holidays!

Top Holiday Experiences in Chicago

  1. Christkindlmarket (Daley Plaza)

Running from November 17 through Christmas Eve, Christkindlmarket Chicago brings the charm of traditional European holiday markets to the heart of the city. Explore unique vendors, sample seasonal treats, and discover one-of-a-kind gifts amidst a festive atmosphere. Named the #3 holiday market globally and #1 outside Europe last year, this market’s enchantment extends to Aurora and Wrigleyville for a broader celebration.

  1. Lincoln Park ZooLights (Lincoln Park)

From November 17 to January 7, 2024, be captivated by Lincoln Park ZooLights. With new displays, festive photo opportunities, and a host of interactive programming, this event promises a dazzling experience. Enjoy traditional favorites like the Light Maze, Ferris wheel, and live ice carvers. Don’t miss the garden-themed light show, the North Pole at the Pepper Family Wildlife Center, and indulge in festive treats and cocktails at Snowy’s Spirits & S’mores.

  1. Light Up the Lake (Navy Pier)

Running from November 24 to New Year’s Eve, Light Up the Lake at Navy Pier is Chicagoland’s largest indoor/outdoor holiday extravaganza. Immerse yourself in a stunning lakefront light display, outdoor ice skating, holiday workshops, and more. From s’mores making to unique activities like axe-throwing, this event offers a diverse range of attractions. Live music, rides on the heated Centennial Ferris Wheel, and Saturday night fireworks add to the festivities.

  1. Warm Bevy Walk & Open House & Window Decorating (Evanston)

Holiday shopping just got a whole lot better. On December 14 from 4:00pm-7:00pm, head to downtown Evanston and explore dozens of shops, restaurants, and other businesses offering warm beverages and shopping or dining deals. Tickets are $10 per person, and a portion of ticket sales will be donated to a local nonprofit.

Also happening in downtown Evanston? The 9th Annual Holiday Window Decorating Contest. Kicking off Small Business Saturday (November 25), Evanston businesses will decorate their windows with a “Glitter & Glow” theme. Check out all the windows, then vote for your favorite on the Evanston Holiday Window Contest Facebook page. Winners will be announced December 23.

  1. Polar Express (Union Station)

Embark on a magical journey aboard the Polar Express departing from Union Station. Running throughout the season, this hour-long trip to the North Pole offers hot cocoa, shortbread, and entertainment by dancing chefs. Join in caroling, receive a special gift from Santa, and experience the enchantment reminiscent of The Polar Express movie. A sensory-friendly train on December 31 at 2:00 pm caters to guests with autism or sensory processing disorders, ensuring a welcoming experience for all.

Don’t miss out on these extraordinary Chicagoland holiday experiences, each offering a unique perspective on the festive season!