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Write a review. …Insure on the Spot Apr 2001 - Present 22 years 11 months. 5485 N Elston Ave Chicago IL 60630 Education City Colleges of Chicago-Wilbur Wright College ...5/5. L. Louis B. 01/18/2024 , IL. My experience with Insure On The Spot, thanks to the agent of Whom I spoke with Anna she was awesome. I had no problem understanding her. She was curious, understanding, she was very professional, and she resolved my issue. Thank you Anna. Sincerely, Louis Barney.Contact Information. To reach Insurance On The Spot, you can contact them by phone at (773) 202-5060 or visit their website at insureonthespot.com. They are located at 5485 N Elston Ave, Chicago, IL 60630. Phone number: (773) 202-5060. To get in touch with Insurance On The Spot, simply dial (773) 202-5060.Insure On The Spot. 296 likes. 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