Toronto - Quito via Cleveland and Houston, do I check in for every flight?

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Accepted answer

As you have one number for your entire reservation, your baggage will be checked in once.

You will also get boarding passes for all your flights when you initially check-in at Pearson.

The only glitch in the process is that US has their own immigration/customs policy which applies to all passengers, even those in transit. You have to go through immigration and passport control. Thankfully, you can do this process directly at Pearson (here are the details); effectively making you a domestic passenger once you land in the US.

Now all that's left is the waiting :)

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