Can an H-4 visa holder travel to the US via Canada without a visa?

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Accepted answer

The fact that it is the initial trip to the United States does not change anything.

An Indian citizen generally needs an airport transit visa for transit in Germany. However, holding a visa for certain other countries, including the US, exempts the traveler from this requirement. A transit visa is therefore not needed in Frankfurt.

An Indian citizen generally needs a transit visa for transit in Canada. The only exemption from this requirement is for US permanent residents, not for holders of other US visas. Therefore, a transit visa is required. I don't know where you got the idea that eTA would suffice, but that is incorrect. An eTA is not sufficient in this case.

Also during the entry in US, Do the immigration even bother about the reason for the transit via Canada instead of choosing direct flight to Chicago ?

They may ask about the reason, but any answer will do, whether it was a less expensive ticket or a more convenient schedule.

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