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Having lived for a few months in the GTA (Greater Toronto Area), I can confirm that Mississuaga and Vaughan are commonly considered to be part of the same city unit for the purposes of praying and fasting. That is, you do not say qasr prayers or break fast if you go from one to the other.

Here is an interesting website addressing the question of qasr prayers in the GTA: https://al-m.ca/travel/#gta

The local ulama should also be able to help with any specific questions about travelling questions in the area, since many people have questions about travel prayers!

If he traveled during the fasting of sixty days of Kaffara, he must fast the days of the traveling immediately after the travel and continue fasting the remains days of the sixty. If he traveled  and did not compensate the days of the travel immediately and made a deliberate gap, he will then  need to restart the Kaffara fast again.

Wassalam.

According to the verdict of Ayatullah Sistani, it is not permissible for man during Ihraam to travel in a covered vehicle. If he had no choice but to do that, he has to pay Kaffara which is slaughtering a sheep or a goat and distributing it among poor believers.

Wassalam.

You do not need to perform istikhara prior to vacation. In fact, it is probably better not to do so, unless you have some uncertainty.