It’s possible and can be done even without hiring someone to haul stuff, but it requires planning and patience and preferably the most direct route possible while cutting the encumbrance of what you take along. The key thing is how will you schlep so much stuff when and where you need to do it and how you will control the children while doing so.

And as part of a training exercise for your trip, consider how you would do things in the following extreme situation: diverted to an alternative route involving a connection and getting stranded for two or more nights without a functioning stroller deliverable to you at the connection airport, your checked luggage missing in action and one child sick enough that the child can’t travel further and needs an IV for a couple of nights. This very kind of thing has happened. If you’re ready and able to deal with such an ordeal, then you have a chance to do this better than most.

3 young kids of the mentioned ages and taking them and all of that stuff with you, including two car seats, onto a plane by yourself? It’s not going to reliably happen in any sort of leisurely way unless you manage to draft someone to help, get a volunteer to help during at least some of the processes involved, and pad in sufficient time for all that is invovled.

Unless you have some of the most compliant and clingy two-years-old and four-years-old children on the planet or get help along the way, this sounds like a difficult process from door to door with its own risks along the way.

If you happen to have a body-wearing baby carrier and a collapsible stroller which can carry the baby and one of the other two kids and possibly has an attached standing-board for the third child, then there are ways to do this.

Using CARES harnesses in-flight for the 2- and 4-years olds is what I would suggest as then you don’t have to deal with the car seats beyond check-in — if even then — until you need to use a car at your destination.

An infant in a car seat-stroller with an attached standing board to handle more than just the infant and a body-carrier that can fit the infant and the two-year-old (at your discretion) has worked before if you can get the 4-5 year old to walk easily. This could work even without a wheeled standing board, but then you’re at the mercy of the 4-5 year old’s willingness and ability to walk the involved distances.

The less you need to carry on board the flight or otherwise by yourself, the easier the logistics become to do this kind of trip.

Here is what my semi-durables equipment list for the children would be for such a situation:

1. Body-harness baby/toddler carrier (preferably one able to carry the two year-old too);

2. A collapsible stroller with an infant car seat attachment and an attachable/detachable wheeled standing board for the stroller;

3. Two CARES harnesses for in-flight use;

4. Boxed car seats for the two older children that can be checked-in at the check-in counter.

When having to carry more stuff than you can move by yourself at one time, it’s time to get help and/or be prepared to do the repeated shuffle back and forth to inch your way forward by moving some stuff ahead a bit at a time and repeating it until you get where you need to get to unload what you can. But this could be challenging if in a rush, impatient yourself or dealing with impatient child/children.