Top 10 Chicago Winter Activities with kids


Yes, winter in Chicago is often very cold.  However, it is still a very fun place to visit with kids.  We live in a North Shore suburb of Chicago and will be taking the train into the city all winter with our 4-year-old son, Harry to enjoy fun activities.

Here is my list of the Top 10 #nottobemissed Chicago Winter activities with kids:

  1. The Magnificent Mile Lights Festival Parade – On November 22nd, watch Mickey Mouse and friends light up the holiday lights on Michigan Avenue with this energetic kickoff to the holiday season.  Click here for the official site
  2. Take a horse & carriage ride through the city and enjoy all of the spectacular holiday decor!  Click here for tickets.
  3. Sip hot cocoa and enjoy ice skating on the rooftop at the Peninsula Hotel Chicago.  We did this last year for my birthday on our stay in January and we all had a blast.  Click here to see my review.
  4. McDonald’s Thanksgiving Day Parade Watch celebrities, marching bands, and huge floats march down State Street.  Click here for the official site
  5. ZooLights at Lincoln Park Zoo is an absolute must see for our family each year!  I like to watch the weather report for a night with warmer temperatures and we go then.  Click Here for official site
  6. Ice Skating in Millennium Park– So beautiful to head to Millennium for a skate and visit the famous “Bean” Click here for info
  7. Christkindlmarket – a longtime Chicago favorite traditional German Christmas Festival.  A great spot for a unique gift and some delicious winter treats.  Click here for official site
  8. Winter WonderFest  at Navy Pier – full of rides, music and holiday treats a fun way to spend a cold day with the kids in the city.  Click here for more info
  9. Wonderland Express at the Chicago Botanic Gardens- Harry LOVES trains and we visit this exhibit several times each year.  It’s so fun for kids and really puts you into the holiday spirit!  Click here for my review of the Chicago Botanic Gardens.  Click here for a link to the official website
  10. Holiday Magic at Brookfield Zoo: It’s worth the drive with the kids out to Brookfield Zoo for this fun holiday event!  Click here for details.


Sarah Hirsch
Sarah Hirsch

Sarah is a Chicago-based luxury travel influencer, Virtuoso luxury travel advisor, luxury family travel writer, an Oprah Daily Ambassador, and the founder of Sarah’s best travel companion is her sweet 12-year-old son, Harry. Her favorite getaways include a luxe hotel stay, quality family playtime, champagne & chocolate-covered strawberries.

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