When will ski resorts in the Chicago open for the ski season? The 2022/23 Ski season in the Chicago starts from 2022/11/24. See this list of projected opening dates for Chicago mountains. Important Note: Not all dates listed here are official and final, as resort opening dates are projected and subject to change. Check back for updates on when the lifts are set to start spinning at Chicago, and don't miss opening day at your favorite resort!