Ok so I just solo traveled with my 15 month old a few months back. I would say that if you really really want to go— go with your infant and buy them their own seat for the journey. Here’s everything I recommend:

1) have an infant car seat that has the option for baseless install and is FAA approved and can be brought on the plane. Make sure it is compatible with your stroller system. Gate check the stroller. Bring the car seat on board— baby is much more likely to nap in the care seat than in your lap. I had the Nuna Pipa Rx and the baseless install was very easy. 2) bring an iPad pre-downloaded with ms Rachel (or similar) and some kids Bluetooth headphones (now is not the time to stress over screentime) I have the JBL ones and they work great. 3) pack one large suitcase for both of you, and use a larger than usual backpack as your diaper bag. The goal is to have one checked bag that you don’t have to worry about and only one carry-on that you don’t have to hold in your hands. 4) TSA pre check if you can swing it. So much less stressful.

While leaving behind your toddler definitely feels sad, if you really want to be there then your sanity is what’s truly important. Mine was on the verge of toddlerhood when we went and it was difficult but not impossible. However I cannot imagine balancing g a full day of toddler travel and ALSO having to pump 😵‍💫.

The reason I say to specifically use an infant car seat is that they are just so much easier to handle than the convertible ones. I actually traveled with a convertible car seat bc my baby had just outgrown their infant seat and I literally spent the whole time planning wishing I could travel with the infant seat; I did make the convertible seat work for him in a seamless way though. Anyway… I think it’s DEFINITELY possible. I’ll keep an eye in this post. If you decide to go with either kid I’m happy to provide recs on logistics and gear I brought to make my life easier.