At INSEAD, classes are packed and it would be very difficult to execute your plan to travel every month to North America. It is possible, but it would be tiring and you would have to miss activities and group work, and even classes. The program is divided into 5 periods, with duration of eight weeks per period. During the first two periods, you won't be able to arrange your schedule, the default is spread through five days. For P3 to P5, it can be done, but it would be very challenging especially as you would also want to consider when your target electives are available, and not just choose the ones that give you a longer weekend.
Given the long flight and the time you would want to spend when you visit, traveling during the very short breaks between periods (usually 1-2 days) would be more practical, in my view.
Hope this helps!