Tokyo airports?

Haneda is the closer of the two to the city. It's where I arrived on my trip to Japan two months ago. Easy connections by monorail, airport shuttle, or taxi to the city. I don't have any experience with Narita.

I have flown through both. Transit options are easy and, depending on where you are staying, Narita might be a good bet despite being further out.

As noted, Haneda is an easy hop into town. Monorail into Hammatsucho and connections to the JR line there. On our trip a few weeks ago we did that into the city and taxi to the airport on departure. Taxi fare from a hotel near Tokyo Station ran about US$50. And there are also bus services from there to Haneda which is less expensive.
If you have a Suica card or app, then no need to buy tickets and the cost is very low.

On our first trip, we stayed in Shinjuki and the Narita Express runs there (last stop) so it was very easy and not too long a ride.

Overall, I tend to prefer Haneda as the travel options there work for where we like to stay but you would not have much difficulty getting into Tokyo from either one.

Narita is a little over an hour from the city center and requires catching a local shuttle bus into town upon arrival. The whole operation is pretty efficient but can be time consuming during high traffic times when the buses can be booked solid for an hour or so, requiring a bit of a wait at the terminal.
I always preferred flying into Haneda while visiting Tokyo on business years ago - it's only about 15 minutes from the center which makes grabbing a taxi viable - it's by far the more convenient option.
FWIW, there's also a city airport in Seoul (Gimpo) if your travel plans should include Korea. It too is located close to the city center versus the international airport at Incheon, and there are direct flights there from Haneda.

I fly out of Chicago - I also have the option of Haneda or Narita, non-stops on a couple competing routes.

Just to suggest some other considerations: Post-Covid, I have been traveling to Japan multiple times a year. When I realized that would be the situation, I researched the flight times and decided that ANA landing at Narita would be better for me than United or JAL to Haneda. I also prefer a Japanese carrier to United - better seating in my previous experiences with various Asian routes.

So, I've been landing at Narita which, as indicated above, is farther out than Haneda. There are multiple ways into Tokyo - express trains to different locations of the city. I have been taking an airport limo that drops me directly at the hotel where I stay and picks-up for the return flight. Very smooth connection despite the extra distance.

Narita is fine as an airport - certain preferable to ORD. 2 hour check-in recommended for departure, I have always whisked through. Arrival procedures through immigration are clearly marked as are ground transportation options. Lots of English spoken. I have gotten through immigration in as little as 15 minutes, sometimes a bit longer, but much more efficient than some of the other airports I use.

If I had a choice, which from Seattle we do not, I would choose Haneda. It is not the airport itself I dislike, it is the Narita Express. The ticket purchase process is not easy for first-timers, and if like most people you are heading to Tokyo Station or Shinagawa, you end at a huge and very confusing station (again, for 1st or even second-timers). I am sure for experienced Japan travelers it is much easier, but we are not to that point yet.

On our first trip , in 2019, we flew out of Haneda because free transport to that airport was provided from our Tokyo Hotel, and it was so easy. We landed in San Francisco, not Seattle, but that is OK as we have family there and can always make a short visit.

So for our next trip, our third, I considered heading down to San Francisco to catch the flight to Haneda, or even to LAX to fly into Osaka (which has a direct train from KIX to Kyoto Station). But in the end I decided we could take the Skyliner from Narita to Ueno station for our first night, so I have booked that JAL flight. This is for next November, so I won’t know until a year from now how that works out.

Like ORDtraveler, I much prefer the Japanese airlines for travel to Japan. (And I prefer European airlines for travel to Europe). I had a disappointing experience with United to Japan 30 years ago and will not use them again. We can fly JAL in business class (or First) with miles, so that is our usual choice. But one time when we were out of miles I booked ANA and it was great. I booked Premium Economy because we were paying for it, and they upgraded us to business class at the airport for a small charge. If I were actually paying for tickets again I would choose ANA over JAL.

Piling on to Lola's post above - ANA Premium Economy (at least at Narita) gives you access to the ANA lounge.

I've flown both PE and Business on ANA several times in the past 2 years. Good experiences.

We flew direct on Delta from Atlanta to Tokyo Narita. There is a train from that airport to Tokyo Station, where our hotel was and that worked very well.

A bit more info about ANA Premium Economy - you can get lounge access at both airports - Haneda and Narita. At Haneda, the lounge is right across from the gates ANA uses so it only takes a minute or two to get from the lounge to the gates.

Wonderful staff in the ANA lounge. I had a nose bleed on my recent trip and was sitting in my chair leaning back and holding my nose. Within minutes, one of the ANA staff came over to ask if I was okay and she had a tissue packet and oshiboris (wet napkins) for me. A pleasant surprise.

ANA economy seating is 34" on international flights (which is the equivalent of United's Economy Plus and Delta's Comfort Plus which typically cost extra). However, seat pitch on intra-Japan flights is 31".

Hands down - Haneda.

As others have said, think about where you plan to be in Tokyo. Narita last week was an extremely easy and cheap connection from Ueno Station on the Keisei Line directly into the lower level of the airport. Keisei is a private train company, not part of the JR system.