I suggest you get a travel agent to work this out for you. It will be worth the $100 or so.
You and your girlfriend will also need to carry a letter signed by by both parents outlining your travel plans and saying that you give permission for your daughter to travel alone with the other parent. Canadian customs can be especially picky about this when returning to Canada, and all customs people pay special attention when small children are travelling with one parent. This is a mechanism to prevent international abduction of children.
EDIT: Further to this – my wife and I have different last names. Our children have both last names (but not hyphenated – my last name is their last name, and my wife’s list name is a middle name), but even so, my wife has had problems travelling with the children because of the name mismatch. If this is your situation (i.e. last names are different), I strongly advise that the parent travelling with the children also carry a copy of your child’s long-form birth certificate that lists the mother’s and father’s names. i.e. you may need some proof that you are the parent. Again, this is particularly the case for young children that cannot convincingly speak for themselves (i.e. it’s different if you are 4 years old, vs 14).
It depends on the airline.
Online booking systems (at least the three first I tested) usually don’t allow separate tickets for children to be booked.
Since most airlines require smaller children (e.g. below the age of four) to always be accompanied by an adult, they may or may not also require that the child and the guardian is booked on the same ticket, in which case you might end up with six one-way tickets (probably very expensive) instead of three return tickets.
Technically there is no issue with you creating 3 separate itineraries for 3 separate people and flying in any way you see fit.
There are restrictions that countries and airlines place when a minor child is flying out of the country of residence/citizenship with only one or no parents with them.
You will need a letter from your girlfriend that says that your daughter is allowed to leave the country with you. This particular subject had been discussed many many times on this forum.
How old does a child need to be to sit separately from parents when flying?
Do both parents need to apply for a US passport for minors?
Travel Consent letter for child traveling with parent to Netherlands
When a mother travels with baby (2 years) without father, what documents she needs to have for baby?
Just to list a few.
Credit:stackoverflow.com‘
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