Get ready to plan your perfect 2024 Chicago holiday! We’ve curated a selection of resources to help you discover the best holiday markets, delightful afternoon teas, and festive activities. Whether you’re seeking a cozy escape or exciting experiences, we have everything you need to make your holiday season in Chicago truly memorable. Let’s dive in and explore the magic of the Windy City!

Outdoor Holiday Attractions

❄️ Christkindlmarket – Christkindlmarket downtown is the quintessential Chicago holiday experience. With two locations, Daley Plaza and Aurora, enjoy shopping, drinking, and eating through this festive German village. The annual holiday mugs are super cute this year! If you’re a cheese-lover, don’t miss the Raclette sandwich! Free to attend. Both locations open on November 22, 2024.

❄️ Winterland at Gallagher Way – My family and I love visiting Gallagher Way during the holidays! This year features bumper cars, Santa’s Chalet, live music, and concessions. More info on ride tickets is coming soon! Free to attend. December 6-22, 2024.

❄️ ZooLights at Lincoln Park Zoo – This event is one of our favorites of the year! Lincoln Park Zoo transforms into a magical wonderland filled with sights and fun. With over 3 million lights, you can enjoy live ice carving, ride the Ferris wheel, roast s’mores, and much more. Most Mondays are free, while other days range from $7 to $10. November 15, 2024–January 5, 2025.

For our complete guide to Outdoor Holiday Attractions, see Bright Lights in the Big City: Chicago Outdoor Holiday Attractions

Ice Skating & Curling

❄️ McCormick Tribune Ice Rink in Millennium Park – The rink is right below the Bean and has incredible skyline views. Reservations open two weeks ahead of the session date. Admission is free, and ice skates can be rented for a fee. Skate rentals start at $16. November 15, 2024 – February 2, 2025.

❄️ The Ice Skating Ribbon at Maggie Daley Park -This beautiful outdoor rink gives you great city views. Online reservations are released two weeks before the session date. Skate rentals start at $17. November 15, 2024 – March 9, 2025.

❄️ Gwen’s Winter Curl & Chill – The Gwen Hotel offers curling on its rooftop terrace and a cozy menu with boozy winter cocktails. The ticket price includes one hour on the curling court, access to a firepit table, and a seasonal treat. Tickets start at $25. November 23, 2024 – March 9, 2025.

For our complete guide to ice skating and curling in Chicago, see Winter Magic: Best Ice Skating and Curling Spots in Chicago.

Fun and Free Holiday Things to Do in Chicago

❄️ Light Up the Lake – Light Up the Lake at Navy Pier features tons of outdoor lights that you can stroll through for free with an incredible city skyline behind you. They’re advertising a new ice slide, axe throwing, and firepits on top of their usual carnival rides like the Centennial Wheel and teacup ride. Free to attend. November 29 – January 5, 2025.

❄️ Hyde Park Holly-Day – The University of Chicago presents a day of free, fun activities for the whole family, like ice skating (yes, even free skate rentals!), ice carving demonstrations, holiday crafts, photos with Santa, live reindeer, Buddy the Elf, and more! December 7, 2024.

❄️ Southport Holiday Stroll & Cocktail Crawl – is free to attend and includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises! The Cocktail Crawl starts at $25 per ticket but they sell fast! December 6, 2024.

Click here for our complete guide to Fun & Free Holiday Things To Do in Chicago! 

Chicago Holiday Ticketed Events

❄️ MSI Christmas Around the World: MSI’s annual Christmas Around the World and Holidays of Light exhibitions are always awe-inspiring! Included in General Admission, tickets start at $26. Open now through January 6, 2025.

❄️ Jack Frost Winterfest Pop-Up: The ultimate holiday pop-up, Jack Frost has 1 million lights, ice skating, holiday pop-up shops, axe throwing, cocktails, and bumper cars. What more could you want in a winter fest? They have tons of price options depending on what activities you want to do, but the bumper cars are included in all packages! Tickets start at $24. November 22, 2024 – January 5, 2025.

❄️ The Hip Hop Nutcracker at CIBC Theatre: We heard great things last year about this fun and family-friendly show! Tickets start at $35. December 10-15, 2025.

For the full list of tickets we recommend snatching up ASAP, get a Head Start on Your Chicago 2024 Holiday Plans.

Afternoon Holiday Teas in Chicago

❄️ The Gwen Hotel—Tipsy Tea at the Gwen is a favorite of mine for ladies’ brunch! This year’s theme is Martha May Whovier’s Christmas Grinch Tipsy Tea. Adult tickets start at $70. This would make a great holiday outing with friends!

❄️ LondonHouse Chicago – LH’s tea service is offered daily in the Bridges Lobby Bar, on the second floor of the hotel with stunning views of the Chicago River and famous bridges. The Holiday Tea menu begins November 20 and is $95 per person, which includes your choice of Rare Tea Cellars tea, a pastry basket, and an adorable tea tower.

❄️ The Langham Chicago – We love tea at the Langham! Executive Chef Damion Henry presents a delectable sweet and savory holiday journey designed for the naughty and nice. Tickets are $70 for children and start at $145 for adults.

See more at Winter Magic: Best Holiday Afternoons in Chicago

Best Festive Bars and Restaurants in Chicago

❄️Santa Baby – Wrigleyville. Bamboo Club transforms into an over-the-top Christmas decoration extravaganza. It’s great during the day for the family! You can make a reservation online if you want to eat, but walk-ins for photo ops and bar service are welcome. Beginning in December, all reservations and walk-ins may be subject to a $5 cover charge. Santa Baby is 21+ only after 8 pm. November 21, 2024 – January 5, 2025

❄️The Christmas Inn on Hubbard Street – River North. Love Hubbard Inn for girls’ brunch! Make your reservations now! November 26, 2024 – January 1, 2025

❄️Butch McGuire’s – Gold Coast. Last but not least is our annual tradition of visiting Butch McGuire’s! This tavern has the best old-school classic decorations! MY FAV! Kids are allowed before 8 pm. No reservations, go as early as possible! November 4, 2024 – late January

Click here to get the full list of the best-decorated Christmas bars and restaurants in Chicago!

Holiday Markets in Chicago

❄️ Chicago Artisan Holiday Market at Artifact Events – November 30-Dec 1. Featuring over 200 artisans, this market has two buildings, two floors, and three bars! General Admission is $8 in advance.

❄️ Winter Wonderland Craft & Vendor Market at Gallagher Way – December 6-8. Winterland is always a good idea!

❄️ Hyde Park Holiday Market at The Promontory – Presented by the Hyde Park Farmers Market, this event is on December 14 from 9 am – 2 pm.

Our full list of Holiday Markets is here!

Gift Guides and the CGL Store

I opened my first e-commerce shop last month! See my curated gifts for the Chicago Lover here!

And finally, you can see all my Holiday 2024 Gift Guides here!

OK, Chicago, there’s still more we need to update, but here is last year’s guide to holiday hotels in Chicago and my list of the best indoor hotel pools!

Happy Holidays, CGL Fam!

Christine