I would always bring a stroller if:
-you are travelling without a significant other or help. If you are alone bring a stroller.
-have more than one plane to catch, especially if there is a long lay over.
I may not bring a stroller if:
-your traveling with help and it's only one flight (bring a carrier for a little baby and something to occupy a toddler.
My first time flying alone with my son, I decided not to bring a stroller, just a carrier but it was much to stressful. Now that he's almost two and a half I'll still bring the stroller anytime I am flying alone with him and most of the time I'm with my husband. A stroller does so much more than just hold the baby, it can also hold all your stuff (and you tend to have most stuff with kids) when your little ones are running around.
Tips for flying with a stroller:
-don't bring a complex, giant stroller: a small umbrella stroller or other light weight stroller is ideal (I'm a fan of the Combi strollers myself)
-check the car seat: unless you plan on using the car seat in the plane or you have a snap and go stroller, I'd leave (check it or rent one) the car seat, it's one less thing you have to worry about before and after you board the plane
-with 2 kids (not twins) bring a carrier for one child and a stroller for another. This way you don't have to deal with a giant double stroller but the kids can take turns depending on need (big kid wants to stroll, use carrier for baby, big kid wants to walk then either use the stroller for stuff or the baby)
Second time time Tavish and I flew, I was smarter this time flying with a stroller. Our Valco strollers a little big and complex to fold for in an airport, I got smarter over time.
Flying with my Combi Stroller (perfect airport stroller) - on the tram to the airport.
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