HND / NRT international connecting flights

I am planning to fly ANA connecting through Tokyo.
Both legs are international flights.

Flight from Chicago scheduled to land in Narita at 8:20pm
Flight to Singapore scheduled to depart Haneda 12:15am

Effectively 4 hours to change airports for international flights. Is this advisable?

4 hours to navigate immigration, transport to other airport and within the time needed for international travel out of Japan is too little. I would advise against it.

Not advisable.

Yes, no problem.

Thanks everyone. I suppose a 3hr transit between two international flights (ORD-NRT / NRT-SIN) in NRT is doable? I will probably opt for this option though timing is less ideal.

Do you know how you'll get to Haneda?

Nevermind.

Better to do the ORD-NRT / NRT-SIN connectiing flights unless there is a significant price difference. Otherwise with the NRT-HND connection you have to contend with passing through Japanese immigration/customs, retrieving luggage, transport to Haneda and worrying about making your connection.

No, It takes at least an hour to clear immigration and custom alone, and 1.5 hours from Narita to Haneda airport (and since it's late at night the train frequency will be much lower). Plus the train from Narita to Haneda is not going to be cheap. and if you carry big luggage changing trains is gonna be difficult. I am not sure if there's bus service between those airports, however i bet if there is, it's only gonna be once for every hour.