- Holiday Afternoon Tea Service at The Drake Hotel
- The Drake Hotel’s Holiday Afternoon Tea in the Palm Court is a cozy and elegant way to celebrate the holiday season. Enjoy a selection of seasonal teas, sandwiches, and pastries.
- Location: 140 E Walton Pl, Chicago, IL 60611
- Pricing: Adults $79 | Children (3-12 years old) $35
- Hours: November 22nd – January 5th, Open Daily, 11:00AM – 5:00PM
- Wicker Park Winter Farmers Market
- The Wicker Park Farmers Market brings together over 50 local vendors offering everything from fresh produce to artisanal goods and ready-to-eat meals. It's a great spot to support local businesses and enjoy a cozy neighborhood atmosphere
- Location: 2018 W North Ave, Chicago, IL 60647
- Pricing: Free admission
- Hours: Every Sunday, December 1 - March 30th, 9:00AM - 2:00PM
- Visit the Christkindlmarket Market
- The Christkindlmarket in Chicago is a festive tradition inspired by European holiday markets. There are about 150 vendors offering unique handcrafted gifts, ornaments, sweet treats served in souvenir mugs.
- Location: 50 W Washington St, Chicago, IL 60602
- Pricing: Free admission
- Hours: Sunday - Thursday 11:00AM - 8:00PM and Friday - Saturday 11:00AM - 9:00PM
- Ice Skating at Maggie Daley Park
- Skating at Maggie Daley Park offers a unique winter experience with its winding outdoor ice skating path, set against the backdrop of downtown Chicago's skyline.
- Location: 337 E Randolph St, Chicago, IL 60601
- Pricing:
- Monday - Thursday – With Skate Rental: $17 online or $19 walkup, No Skate Rental: Free.
- Friday-Sunday - With Skate Rental: $21 online or $23 walkup. Skate with your own skates – Free 11am session only
- Hours: Open 7 days a week: 11:00AM – 1:00PM, 2:00PM - 4:00PM, 5:00PM - 7:00PM, 8:00PM - 10:00PM
- Visit Jack Frost's Pop-Up
- Jack Frost Winter Pop-Up in Chicago's Fulton Market is a festive outdoor experience for all ages, running from November 29, 2024, to January 5, 2025. Visitors can enjoy ice skating, axe throwing, bumper cars, holiday-themed pop-up shops, and a great light display.
- Location: 170 N. Green Street Chicago, IL 60642
- Pricing: $18-$143 ticket options on the website
- Hours: Monday - Friday - 4:00PM - 10:00PM, Saturday and Sunday 11:00AM - 10:00PM