fly into ?

CDG for most international flights. We used Orly for flights within Europe.

I haven’t seen any flights from the PNW going into anywhere but CDG.

If you’re at all concerned about something interrupting your trip or canceling before you’ve even gotten onto the plane, get travel insurance. If bought as soon as you’ve booked, the cost for “any reason” will be lower and more affordable. A refund, flexible ticket will be a lot more and you’ll still have to worry about accommodations and the like.

If you prefer a direct flight from the Seattle and the USA than CDG is the best airport.
Looking at fares today from Seattle May 2020 the lowest price I see is $609 but that requires a connection. The best prices for direct flights are about

$ 1100. Whatever you do try not to go in June July or August if you want to avoid overbookings. I know this because I worked at an airline during those months and we use to do this on purpose but had plans and briefings on how we would reroute passengers.

You have to pay a lot more than the prices I am seeing if you want a refundable ticket or one that allows changes. All airlines have this option.

It never fails to amaze me that you can fly from the west coast to Europe cheeper then I can fly from Detroit...

actually, it never fails to surprise ME that people only consider direct flights....;-)
I am a little confused about the comment 'cancel for any reason is cheaper'. Maybe compared to walk up flight tickets, but not for general insurance....and it isn't as available.
Regardless of the insurance bought, a challenge is that there is only so much that an airline can do these days to get a person home 'now' particularly at high peak season. They overbook all flights, so the next 'available' flight might be several days after the ideal time. Alternatively you may be willing to pay for business class to get a seat, but you will never be able to get all of it reimbursed.
When you price out tickets, all the options of changes, refunds, etc are well documented before flying. Perhaps just a general look at your airline of choice's ticket options will educate you on that.....but it still may not get you home if there are no seats available...and you may still need to pay the balance of the ticket cost.

As for when to book your flights, a couple of years ago I kept a spreadsheet tracking the price of flights from Vancouver, Canada to Paris CDG using prices from Google flights. I tracked about 8 different itineraries over the course of about 6 months for a trip we were taking the following September. For 7 of the 8 flights, the cheapest airfares occurred during the week between Christmas and New Years. I have no idea if this would have been true had we been flying in May.

The other option you may want to consider is flying from Vancouver, BC. Air France has a direct flight from Vancouver to Paris as does Air Canada and with the current exchange rate between the USD and CAD it may be cheaper to fly from here. Air France flights to Paris CDG leave Vancouver around 5 pm so you could drive or fly up the same day.

You may also want to consider tracking flight costs using the mobile app Hopper. You enter the flights you are interested in and it lets you know whether the historical data suggests that the cost of the flight is likely to decline or if the current price is a good one.

If the dates of your trip are flexible, the best advice I ever got was to create a rough itinerary and decide how much you are willing to pay for a flight. Then find flights that fit your timeframe and budget rather than searching out the cheapest flights as you may end up staying more nights and the cost of the hotels, meals etc. will always cost more than what you saved on airfare. If, however, you have fixed dates for when you travel you may have to look at a lot of different options to find a reasonably priced flight. The other piece of advice I have found useful, is once you've booked your flight don't check to see if prices decrease. Just move on and start planning for a wonderful holiday.

As said above, if you want a nonstop flight from anywhere near you, CDG is the only option.

Orly (code ORY) gets connecting flights from many European airports. It gets flights from JFK (on Air France), Newark (on La Compagnie), and part of the year from Montreal (on Level).

If you have a choice with a European connection, Orly is closer to Paris and is a cheaper taxi ride than CDG. By mass transit, it's not so much different. I certainly wouldn't choose a route from Seattle to JFK to Orly, over a nonstop from Seattle or Vancouver to CDG, just to fly into Orly instead of CDG! But, if you're connecting in Europe anyway and the price is the same, you can choose Orly.

Paris's "third" airport is Beauvais (code BVA), which is far from Paris and only gets budget flights, mainly Ryanair.

To learn who flies from an airport, look at that airport's Wikipedia page.

I agree that if you want "flexibility" for family emergencies and the like, use travel insurance. Just make sure the policy covers what you need. If you want "flexibility" for the ability to change your mind (not for emergencies, medical situations, etc), then you can buy "cancel for any reason" insurance, although note that you only get 75% of your costs back if you cancel for reasons that would not be covered by other policies. Or, you can buy flight tickets that are more flexible (for instance, they may allow changes after ticketing for a fee, rather than being completely non-refundable and non-changeable). Tickets that are fully refundable (not just changeable for a fee) cost a fortune.

Note that things can be covered by insurance you didn't expect. A coworker wanted to be covered if she canceled her flight because her grandson was hospitalized. She assumed she'd have to get a cancel for any reason policy, but reading the fine print, grandchildren were included as "family members" in that company's regular "illness of a family member" policy, so extra cost coverage wasn't needed for that purpose.

My experience has been that non-refundable prepaid reservations can still be changed, for any reason, for a fee in the $100+ range. You won't get a refund if you just cancel the trip, but you should be able to reschedule the flights (to and from the same airports) for a fee that doesn't break the bank. And/or there's trip insurance as described above.

I'd start looking now at airfares for next May, though it's unnecessarily early to buy now. Get an idea of what fares are, check back and look for trends. Kayak.com is a good search engine and I believe you can set up price alerts (maybe getting more info than is really useful). But try to book the flights directly with the airline so you don't have to work through a third party if there's a problem later. I have yet to find a third-party fare lower than what the airline itself offers.

Icelandair might be a good choice if you don't mind a brief (or longer) stopover in Reykjavik. They have been serving PDX, I think they still do. Generally lower fares than nonstops, and the food isn't free, but they get you where you're going.

Try insuremytrip.com to shop for travel insurance, if you decide you want it.

I've been able to fly into Orly by using Iceland Air. Since they are also a Schengen country, you get your passport checked quickly while changing planes then some flights fly into Orly. The good thing (even if it's into CDG) is there is no passport line on arrival. If you carry on, there's no wait for luggage either. Orly is better than CDG because it's smaller and closer. It regularly takes me an hour to get on a train out of CDG (already having passport stamped and no checked bag) but takes less than half that to get out of Orly. The ride from CDG to Paris is roughly 50 minutes (depends on where you get off) while the ride from Orly is about 30 (depends on how tight the connection between the Orly Val and RER).

CDG or Orly