One of my friend gave me the following suggestion:
I guess ICl will break in the form I+/Cl- so considering this if I+ gets attached to the lower side of the chain then the carbocation formed on the 2nd element of the chain will not be a non-classical carbocation (because I+ won't give a lone pair to the carbocation as it is electron deficient itself). A simple carbocation will be formed, and the rearrangement will be possible.
After rearranging it will get its most stable position on the carbon joining the ring and the chain so there the Cl- attacks and the requires molecule is formed.
I suspect this is wrong, What is the solution to this problem?