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Please critique my plan for flying w/2 kids!

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Alrighty, this is a long one, please bear with me!

I'll be flying to PEI, Canada at the end of June alone with my 18mth old and about to turn 4 year old.

We will be flying AUS to ORD to YUL to YYG! (Yes, I know this is insane.) The first flight is at 6am. The connections are both about 90 mins.

The flights are Air Canada (some are code share with United, I think). AC has a very restrictive stroller policy. The stroller must collapse like an umbrella stroller (not just fold over) and have a collapsed diameter of 10 inches or less and a length not exceeding 36'' in order to be gate checked. So no piling my crap on a huge double and wheeling it through the airport. :(

I will be staying at my mothers house when we get there (no hotel). My husband will be with us on the return flights so I'm don't need help with those :)

Here is my super duper plan to survive this:
- I'm going to buy this stroller http://www.amazon.com/gp/aw/d/B009H5B1HK/ref=ox_sc_act_image_4?ie=UTF8&m=A1D793VGWZIR4D
It meets everything except the length requirement, and I haven't found any stories of AC actually measuring the strollers, so I think I will be okay (if you've heard otherwise please tell me) I really need a double
- I'm packing everything we need for the flight in a back back. Everything else will go in a small duffel bag (like 18" long max) that I can hang on the stroller or sling over my shoulder.
- I'm not checking any bags. My mother can purchase toiletries and such on her end before I get there. In theory I could mail some things but I don't think I'll need to. Hopefully this will save time in customs in YUL as well as make life easier if we miss a connection and have to change flights.
- I'm renting a Cares harness for my youngest because there's no way I can carry a car seat through the airports
(Yes, she has her own seat booked)

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