Must-Attend Chicagoland Events for Fall and Winter 2024

As the seasons change and the days grow shorter in Northern Illinois, it's a wonderful time for area families and homeowners to explore their surroundings. Our region provides a wealth of events and activities that can help you settle into your community, meet new people in the place you call home, and fully embrace the season. Whether you're looking for family-friendly activities, seasonal festivals, or unique local experiences, Northern Illinois has something to offer. This guide will take you through some of the most exciting Chicagoland events happening this fall and winter, with a specific focus on the best events for new homeowners and those thinking about moving to or within the region.

Fall Chicagoland Events for Families and Homeowners

Wicked Wilmette

Location: Wilmette, IL

Dates: October 19th, 2-4 pm 

Get in the spooky spirit with this family friendly event that features inflatables, face painting, magic shows, games and more. Visit the Spooky Stations scattered throughout the park to collect various giveaways and treats, or explore the pumpkin patch and choose a pumpkin to decorate.

Woody’s Farm Fall Festival

Location: Plano, IL

Dates: September 11th-October 27th

Head out to Woody’s Farm in Plano to enjoy their play yard, corn maze, pumpkin and sunflower patches. Invite all the neighbors and enjoy the festive atmosphere together.

Evanston’s Bug a Boo

Location: Evanston, IL 

Dates: Month of October

Take a trip to the Ladd Arboretum in Evanston to learn more about the creatures that call the North Shore Channel home. You’ll meet these characters (represented by costumed volunteers) on the grounds of the arboretum. Then, they’ll send you home with a fun craft to continue your family’s learning about local ecosystems.

Naperville Farmers Market

Location: Naperville, IL 

Dates:  Every Saturday (June-October), 7 am-noon

Naperville’s farmers market is a charming event that runs through the fall, featuring an array of vendors selling gourmet foods, handmade crafts, and unique gifts. This market provides a great opportunity to do some early holiday shopping and enjoy some seasonal treats. It’s also a chance to experience Naperville’s lively community and meet local artisans and business owners.

Winter Chicagoland Events for Families and Homeowners

Light up the Lake at Navy Pier

Location: Chicago, IL 

Dates: December 6, 2024 - January 12, 2025  

This holiday event transforms Navy Pier into a holiday extravaganza filled with lights, decorations, and ice skating. This event is perfect for Northern Illinois residents who want to embrace the winter season with festive cheer that makes the most of their proximity to a world class city. The festival includes a variety of attractions such as a wide variety of ice sculptures, a giant indoor alpine ice skating rink, holiday themed train rides for kids, and an authentic winter beer garden. It’s a magical experience that can help you get into the holiday spirit and explore one of Chicago’s easily accessible, iconic landmarks.

Lights of Lisle

Location: Lisle, IL 

Dates: December 7th, 2024, 4:00-7:30 pm

Head to Lights of Lisle to meet Mr. and Mrs. Claus, take in the Santa parade, participate in holiday craft projects, sip hot chocolate, and shop small at local businesses. New homeowners and area families might just find that this becomes an annual tradition.

Outdoor Ice Skating

Location: Various locations throughout Northern Illinois

Dates: Beginning in December, continuing through the first thaw

Northern Illinois is home to a variety of outdoor ice rinks that offer opportunities for area families to get active outside, even when the temperatures drop. Most rinks listed at the link above are open through the winter season. Whether you’re an experienced skater or just looking to try it out for the first time, this is a great way to engage with the local community and enjoy some winter exercise.

Hinsdale’s Winter Wonderland

Location: Hinsdale, IL

Date: December 3rd, 2024, 9 am - 1 pm

Take the family to KLM Park in Hinsdale for tons of seasonal fun, including photos with Santa and Mrs. Claus, a meet and greet with characters from Disney’s Frozen (including Sven in real life), a hot chocolate bar and treats station, live reindeer, and train rides. Donations will be collected for Toys for Tots at the event. Pre-registration is required.

Tips for Making the Most of Chicagoland Events this Fall and Winter

Contrary to popular stereotypes about Chicagoland, you don’t have to stay stuck inside as soon as the weather begins to turn colder! Instead, take this advice to make sure you’re out and about enjoying everything our region has to offer this fall and winter:

• Stay Connected: Sign up for local newsletters and follow community social media pages to stay informed about upcoming events and activities. Many communities have local groups or forums where events are posted regularly.
• Volunteer: Volunteering at local events is a great way to meet new people and get involved in your community. It’s also a rewarding way to give back and make a positive impact.
• Explore Local Attractions: In addition to seasonal events, take the time to explore local attractions such as parks, museums, and historic sites, both in the suburbs and in the world-class city that can be easily accessed from whichever town you call home.
• Network with Neighbors: Don’t hesitate to introduce yourself to your neighbors and ask about local events and traditions. They can be a valuable resource for discovering hidden gems and getting acclimated to your new community.
• Plan Ahead: Many events, especially popular ones, require advance registration or tickets. Make sure to plan ahead to secure your spot and avoid missing out on any exciting opportunities.

As a homeowner in Northern Illinois, embracing the fall and winter seasons offers a fantastic chance to immerse yourself in the local culture and connect with your new community. From fall festivals and cozy winter markets to vibrant holiday displays and outdoor activities, Northern Illinois has something for everyone. By participating in these great Chicagoland events, you’ll not only enjoy the seasons, but also create lasting memories and build meaningful connections near home. So, grab your calendar, mark these dates, and get ready to explore all the wonderful experiences and events Chicagoland has to offer this fall and winter.