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Looks like this may answer your question.
Seems to me like there shouldn't be any issues crossing back over into Canada with a reptile.
It is true that ‘pet’ reptiles won’t need an inspection and permit at the Canadian border as you cross. However it is a bit more complicated than that when you want to bring back a CITES (Convention on International Trade in Endangered Species) declared animal and most chameleon species fall under that umbrella. You will need an official CITES export permit from the seller and an inspection by the USFW before you leave American soil. If the Detroit/Windsor crossing is not a designated port there won’t be a USFW inspector working and you have to arrange in advance for one to be there to check the animals listed on your export document and stamp it. I know at one point reptiles were banned in Windsor but I think they have recently moved to the No Hots, No Crocs, 1 meter and 2 meter reptile bylaws prevalent in other communities. If not, then there may be problems when you enter Canada.
Here is a good thread about smuggling chameleons into Canada: https://www.chameleonforums.com/question-legality-106870/
Here is my blog about Importing into Canada: https://www.chameleonforums.com/blogs/trace/783-import-export-cites-animals-canada.html
Probably not. Besides there is a great reptile and exotics pet store down your way. I thought I would mention it anyways just so you and other people who read this thread now and in the future are aware of international and provincial laws and city by-laws. I don't always agree with the laws but flaunting rules and getting caught only serve to put even more restrictions our hobby by people who don't understand or are scared of these animals.
There is no selling reptiles in Windsor but I'm actually technically Tecumseh so it shouldn't be a issue
I definitely won't try to bring one home if it's against the rules because I would never want someone to take it away and destroy it, and it would just make them crack down on the laws even more. If I was going to bring one home I would get all required documents and have the inspection at the border. It seems like a lot of work so I will only be bringing back feeders (hopefully I get some bluebottle or house flies as I can't find any here)Trioceros sternfeldi may not be on the CWS species of concern as they are not endemic to Canada. However almost all chameleons are listed as CITES Appendix II (some are Appendix 1 and their trade is closely monitored, if permitted at all) and thus permits are needed.
Here is a another good site that explains what you will need: http://travel.gc.ca/travelling/documents/cites-permits
CITES Appendices: (Reptiles are about half way down) http://www.cites.org/eng/app/appendices.php
Crossing without the proper CITES documents would be a violation of international law. If caught, the animal would be confiscated and possibly destroyed, and you could be subject to hefty fines and jail time if convicted. If you want to try it your way, then go for it. I'm just letting you know what the rules are.