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Package #3: A Forecast You Won't Forget: Dinner for 8 With Tom Skilling at The Dearborn

Legendary WGN-TV weatherman Tom Skilling’s 45-year career made him one of the most trusted and beloved figures in Chicago broadcasting. Now you and 7 lucky guests have the opportunity to share a private table with Tom at The Dearborn in downtown Chicago.

Known for his heartfelt delivery, passion for meteorology, and uncanny forecasting accuracy, Tom will regale you with behind-the-scenes stories, fascinating weather insights, and unforgettable memories from his decades on the air. From epic blizzards to live TV moments that only Tom could make feel personal, you'll get a front-row seat to the career of a true broadcasting legend .. and maybe even an exclusive forecast or two out of retirement!

Adding to the evening’s charm, WGN’s Weekend Morning News co-anchor Sean Lewis—another fan favorite—will join the dinner, making this an even more exclusive gathering of Chicago media greats.

This is truly an unattainable opportunity to spend quality time with a couple of “Chicago’s very own” in a relaxed, intimate setting—complete with great food, great stories and great company.

Package includes:

  • Private five-course dinner prepared by Chef Cushieri for 8 at in the Rialto Room at The Dearborn in downtown Chicago
  • Each course will be expertly paired with wines courtesy of Southern Glazer’s Wine and Spirits with a Master Sommelier. 
  • Special guests: Tom Skilling and Sean Lewis
  • All taxes and gratuities included (additional gratuities optional)

Restrictions: All purchases are non-refundable. Earliest start time must be 5pm and latest start time is 8pm; meal will last approximately 3 hours. Date must be mutually agreed upon and take place prior to 12/31/25.

Donated By: The Dearborn, Tom Skilling