Flying into Canada from US
 

I have never flown out of the US before, and this summer I will be flying from Atlanta through Toronto to Calgary. Will I go through customs here in Atlanta or when I arrive in Toronto? Likewise, on the return trip back to Atlanta, will I go through customs in Calgary or in Toronto? How much time should I allow to go through the customs process?

You will go through customs in Toronto. Its not too difficult, you will have to wait for your luggage at the baggage claim, then go through customs. Once you are through, there is a baggage drop for ongoing flights. Then you follow the signs back to the main terminal

Wirelessly posted (BlackBerry: BlackBerry8530/5.0.0.1030 Profile/MIDP-2.1 Configuration/CLDC-1.1 VendorID/417)

The OP will clear Canadian Customs & Immigration in YYZ on the outbound, and U.S. Customs and Immigration at YYZ on the return.

I hope that the OP already has a U.S. passport. ;)

GUV has it right.
OP will go through Canadian Immigration & Customs in YYZ (Toronto Pearson Airport) on the outbound and then proceed as a domestic flight to Calgary.

On the inbound you will go through US Immigration & Customs at YYZ and then land as a domestic flight in the US. I'd allow for a greater amount of time on the return to allow for processing at YYZ for US CBP. I find the Canadian CBP to be much more "friendly" than the US CBP at airports.

As this is your first international flight just be honest if you have anything to declare and wait quietly. It's not difficult or scary.

Customs? Are you bringing things into Canada or do you mean Passport or Border Control? I Married a Canadian. Got Nexus straight away. Crossing in can be tough even for US passport holders. Have your story straight and be clear that you are not working there or staying indefinitely. Customs wise? Are you bringing anything in? Check the limitations of course but I've never been directed to secondary for baggage but have been twice to immigration secondary due to one way tickets with loose plans for a long weekend. CBP at secondary are tough, will go through your cell, visit your Facebook and ask intimate details. Have your travel plans detailed in advance, if you have arrests or convictions be prepared to answer, If you have a DUI be prepared to be turned away if they get interested and decide to run your record.

Yikes!
 

This question is something I did not anticipate when I booked my 85+ year old mother & her friend BDL-ORD-YKF and return YKF-ORD-BDL.

I assume on the outbound they will do immigration & customs in YKF? But how about the return? Where?

I've requested wheelchair assistance for both of them. Will the assistants stay with them for the entire process in both directions? Especially if ORD involves claiming their luggage & rechecking? May not be an appropriate question for this thread but thought I'd ask.

My heart is sinking....

Oh you'll be clearing at T5 at ORD. It's flown on a regional jet so they'll l be exiting on a ramp walkway from the aircraft then walking outside into the terminal. They'll have wheelchair pushers available and yes, they stay all the way though. Yes, they'll be able to recheck the bags once you're through immigration and customs at the American Airlines recheck counter.

YKF is a very small airport - just a few gates - so they shouldn't have any difficulty getting around there - and it likely will be comparatively quick coming and going.

At ORD, the baggage drop will be just ahead past Customs - only takes a minute to stop and drop it off, and the folks doing the wheelchair assist are quite familiar with it (as well as the baggage claim prior to Customs).

They will be fine. I'd make sure they have phone numbers to contact in case of any issues, charged cell phones, and copies of their itineraries (enlarged to a font size they can easily read if need be).

Thank you ords & 84fiero. You can probably understand how things like this look so much more major to two ladies of a certain age who haven't traveled in a while & when they did they were almost always with tour groups & not on their own. Thanks for helping me put their mind at ease (and to OP for forcing me to anticipate the question).