Originally Posted by
evergrn
If your flight lands at 8pm and leaves at 10am, I wouldn't bother. But if it lands at 3pm and leaves at 5pm, or lands in the morning leaves anytime next day, or something like that, it'd be worth it to me. If NRT-NRT, then Ueno is the most convenient. If HND-HND, then maybe Shinagawa. Actually, if you have >24hrs, then you could even stay in the most popular part of town (eg, Shibuya, Shinjuku) rather than prioritize utmost convenience.
Honestly, it doesn't matter that much. NRT is only 45min to Ueno.
45 long minutes later doesn't matter too much if you have a long connection, but arriving at 8pm... to leave the next morning at 10am... with kids I wouldn't do it from NRT.
OP, by the way... I assume your toddler isn't in school. Just FYI, they're free on transportation under 6 usually.