Cubs auction off a few recently used on-deck circles, most went for under $500.
Yours is a bit older and autograph so more than those. If you can tie it to a historic game or event, etc, then a lot more. The Phillies one from the 2022 NLDS went for $2500 The Tristar authentication probably came when it was signed at one of their shows, so probably signed in the past 20 years.
https://cubs.auctions.mlb.com/astros...1/aucd/5010664
https://cubs.auctions.mlb.com/blue-j...1/aucd/5010671
https://phillies.auctions.mlb.com/20...1/aucd/4537468
Google: game used on-deck circles auction, you will get a bunch of results to give you an idea.
If I had to guess, due to its age and autos probably in the $1500-2000 range. Would be worth more if it was the Cubs version.