Itinerary Osaka-Kanazawa-Tokyo

We are having a two weeks trip to Japan to attend the JCI world congress in Kazanawa.
But we decided to go visit Osaka especially Kyoto, then go to Kanazawa then visit Tokyo.
I am wondering if it's a good idea to come through one of the two airports of Osaka (which one is better?) and leave through it as well or leave directly from Tokyo ( which airport would be the best?).
I was also wondering if we can use the JR pass to get through these cities.
Any additional tips?
Thank you for the help!
Cosette

If you coming from overseas, arriving at Kansai International Airport is best for arriving in Osaka (the domestic airport will require another flight).

Kyoto is not in Osaka; it is a separate city about 30 mins away by train. Very accessible from Osaka though!

If you leave from Tokyo, either Haneda or Narita International airports is possible. See what options you have based on airlines flying out of your home country; some may service only one of these airports. Also check to see if it is cheaper to fly in and out of Kansai or to fly into Kansai and then out of a Tokyo airport.

You can use the JR Pass to travel between all these cities, as well as on the JR loop lines within Osaka and Tokyo. However, be aware that a 7-day JR Pass normally pays off with a round trip between Tokyo and the Kansai area; it may not pay off if you do not return to Osaka after visiting Tokyo. Use Hyperdia (hyperdia.com/en) to calculate your train fares once you know your itinerary to decide if a JR Pass is cost effective. It will also depend on how long the congress runs for (no point having a JR Pass that isn't used for several days).

The way I see it, it is best to enter through Tokyo. You can take the shinkansen to Kanazawa.

As the above mentioned you would either have to
Kansai Airport - Osaka - Kanazawa - Tokyo - Kansai Airport
Or
Tokyo Airports - Tokyo - Kanazawa - Osaka - Tokyo Airports

for it to be worth the Japan Rail Pass 7 days. Not only that, the 7 days starts when leaving the city (Osaka or Tokyo) and returning to said city (Osaka or Tokyo).

If all you do is a one direction ride from Kansai Airport to Tokyo Airpots, then a 7 Day JR Pass would not be worth your money. If however, your summit is not very long + you plan to visit Hiroshima, then a Osaka/Kyoto train trip to Hiroshima (1 night), Kanazawa (? nights), onto Tokyo within 7 days will be worth your money.

Thank you for your help!
We were thinking to get a 14 days JR pass
Our trip is
29,30,31,1,2 OCT/NOV :Osaka region
3,4,5,6,7,8 NOV :Kanazawa
9,10,11,12 NOV :Tokyo

We want to use the JR from Osaka to near cities like Kyoto.
-Do you mean the JR would be activated on the 3rd when we leave from Osaka to Kanazawa?
-Do you think there's a better transportation solution other than the JR?

You need to calculate the train fares to make sure a JR Pass will pay off. 14-day Passes are expensive and may not be cost effective for your itinerary.

You can buy individual shinkansen/train tickets if a JR Pass does not turn out to be cost effective.