Thanks for the quick reply. I do realize it will be tight. I did a quick search for Tokyo's Times Square equivalent and found Shibuya Crossing. Routing it on Google Maps, I should have a good 45min there going to HND.
Does that sound feasible? Will I be able to purchase tickets with a CC, and be able to find my way through English signs?
I am more interested with the experience rather than a simple direct ride from NRT to HND.
I am ok considering other options.

Not a good plan for a whistle stop visit. Pick somewhere that’s actually en-route from NRT to HND. For example, Tokyo station area or Ueno station area.

For example
1. Ueno
Take Keisei line to Keisei Ueno. Spend a short time exploring Ameyoko market area. Then get the Yamanote line to Hamamatsu and transfer to the Monorail to HND.
2. Tokyo
Take the NEx to Tokyo station. Have a meal in one of the skyscrapers around marunouchi. Wander as far as the imperial palace and then head back to the station for Yamanote Line to Hamamatsucho (as above)

Would probably stay clear of shibuya/Shinjuku (it's easy to get lost. Good if you have spare time, not good if you're trying to find the right subway/track).

Also depends what you want to do? You can have a 10min meal at a Japanese fastfood place i.e. ramen place/gyudon(sukiya/matsuya/yoshinoya/...) with more time for exploring/buying snacks at Don quijote, or spend 30-60 min on a good restaurant

It's quite common to see people with carryon roaming around (or stick it in a storage locker, but that requires suica or coins/cash. Recent iphones can create virtual suica cards)

Thanks for the feedback. I think I will go to the Tokyo Station and wander around Marunouchi area instead. I can choose a fast food place once there. I don't mind rolling my carry-on with me for the short-time I am there.
For purchasing train tickets, is it an easy thing to do? Will I be able to use a credit card?

For Narita Express and the Skyliner, yes you can pay with a card. For the local trains to Haneda no, you can't pay with a card. But you could probably install the suica app on your phone and use that for the tickets. But be aware that not all non-japan market phones support the right NFC frequencies for suica. Otherwise cash works easy, just buy the cheapest fare, and then go to the fare adjustment machine at the arrival station, and it will tell you how much to top up. This tip will not quite work for transit between yamanote and monorail. But if you take the subway plus keikyu to Haneda, works like a charm.

The ticket machines take plastic so that's not an issue.
For time in town I'd go with the Skyliner from NRT to Ueno. I like the area better with Ueno Park to kill time at being right there, Marunouchi is lots of shops, offices and crowded most of the day. Heading to HND I'd take the Keihin-Tohoku Line to Shinagawa and catch the Keikyu to the airport, The Keihin-Tohuku parallels the Yamanote but there's a lot fewer stops.

There is only one right way to do this transfer:

• Skyliner from Narita to Keisei-Ueno (way faster and cooler-looking than any other option into the city)
• Check out Ueno Park and/or Ameyoko
• Yamanote Line from Ueno to Hamamatsucho
• Walk to Zojoji temple and get a photo with the Tokyo Tower in the background
• Monorail from Hamatsucho to Haneda

For a first-time visitor to Tokyo, taking the subway is a total waste. Stay above ground so you can see things. For the same reason, monorail >>>>[unscalable wall]>>>> Keikyu.

Thanks all for the feedback. I do prefer above ground and sightseeing. I'll use the Skyliner and go to Ueno instead, and like the idea of the Tokyo Tower picture too.
Just a clarification, am I able to pay the train/monorail fares with an international CC? Otherwise, I can withdraw some Yen from an ATM and use that.
For the Skyliner, do you recommend pre-purchasing the ticket online? Can they be used on a later train ride in case there is a flight delay?

From a capacity perspective there is no need to pre-purchase the Skyliner, just show up and buy a ticket for the next. If you arrive with only a few minutes to the next departure, there can be some crowding at the limited express ticket machines, and sales office which you could avoid. But they run every 20 minutes, so it is probably fine to just walk up and buy for the next possible departure.

For the yamanote/monorail tickets you will need cash. Skyliner is fine with a credit card. There may be an option to buy a through ticket from Narita via Ueno and Hamamatsucho, and then you can pay the whole thing with a credit card. But otherwise you will need cash....

If you have a fairly recent iPhone you can download Mobile Suica and charge it with a credit card, then tap in and out of the Yamanote Line and monorail.

Ok. I'll get myself some cash just in case and figure it out once there. Arigato :)

Update regarding HND MCT
 

Just an update for those curious. JAL facilitated the transfer of our family of four and checked luggage both ways with short connections at HND. To SEL our connection time was 30 minutes due to departure delays from ORD; ground staff was waiting for us at the end of the jetway and got us boarding in 15. Returning our departing flight left the gate early, then turned back for deicing, reducing our connection at HND to a mere 25 minutes. We still boarded on time due to phenomenal ground staff at HND and all of our luggage made it to the States. Really incredible.

I have an iPhone 13. I installed the Suica app, but it's all in Japanese. Wasn't able to find how to switch to English. But anyways, to use the app, I suppose data should be enabled, but I am not planning to do so as to not incur roaming charges. It's no big deal, will get some cash.
Thanks though

I think you may have misunderstood. You're adding the Suica Card to your iPhone Wallet not the Suica App. So open your wallet app -> select the "+" in the upper right corner -> Select Transit Card -> Search for Suica -> and then follow the prompt to add the Suica card and add cash to the Suica card using Visa, Mastercard, or Amex (although I read that Visa doesn't work and I experienced that myself so try Mastercard or Amex - I was able to add funds with my Amex).

Oh, I see! I did not know of that feature with iPhone Wallet. Quite handy. I also did a quick search, and I can use it without having internet connection. I hope this will be standardized to other transit places too, as it seems limited to mostly Asia. Thanks