Gamble for Airfare....Cyber Monday? Travel Tuesday? Or grab the fare today???

Those sales you mentioned black Friday cyber Monday travel Tuesday are all hype as every route is not discounted. For example I got a roundtrip for travel in December 2019 from here to Paris and back from Madrid non-stop 2 months ago for $600. When I looked at the same flight black Friday it was $1700.
A flight for $560 roundtrip would have been one to buy.
My niece went to Cornell University and never drove to the airport to get away from there so maybe you can do it that way

There's no way to predict what air fares you will find on any given day. Find something you can live with - it doesn't have to be the absolute lowest price ever, just something you feel OK with - buy it, move on, and don't look back. There's nothing good that can come from beating yourself up over this. Get your ticket so you can start planning the actual details of your trip - worth considering: the longer you wait to nail down your flight, the more you will probably spend on the other trip costs (as good hotel options dwindle with the passage of time), so by waiting and hoping to save money on the flight (no guarantee of that) you can easily end up spending more money.

Personally, I'd happily spend more money to avoid flying through JFK, or other miserable connections, but that's just me - I think far too many people obsess over getting the absolute cheapest flight fare, and that contributes to all sorts of travel misery for all of us.

Airlines don’t publish their sales strategy, so no one on this forum will have heard rumblings. What’s happened in previous years may not occur this year.

Only you can decide if you are prepared to use JFK. If you see a fare that you are happy with, then book it now, then don’t look at prices again!

Re flying out of Ithaca -- flights are just cancelled too frequently...don't want to chance it on a major trip. We've made a habit of driving somewhere and flying direct, rather than starting in Ithaca (where currently the prices are crazy high). Toronto is our favorite airport, but we've also done Philadelphia and would do Newark. About 4 hours to any of them. I wouldn't want a layover of less than 2 hours, so the actual time difference is minimal.

I Fly Delta overseas and I don’t remember them ever sending special discounted deals for travel abroad on Black Friday or Cyber Monday. I don’t think they have a rhyme or reason for releasing special offers at least by email to me. 😂

Yesterday I booked JFK-FCO and CDG-JFK for a departure of late April and a return of late May for $554 total in economy (not basic economy) on American. I was pleased with the price so I bought it. I watch the fares and this was a few hundred dollars below what i’ve been seeing the past few weeks.

Update: Bit the bullet today! Purchased tickets nonstop both ways out of Toronto for $617 (regular economy). These same seats were $749 two days ago. Maybe they'll go lower....but I decided to jump now because we prefer to fly out of Toronto, and parking is a lot easier and less expensive at JFK.

FYI, for anyone following this thread, Air Canada is holding a (supposedly) 1 day Cyber Monday sale. Even though it says prices are good for travel through the end of June only, we found prices for September lower than they've been in the past week.

Update: Bit the bullet today!

Good for you. Now, stop looking at air fares, because you're done with that. Start planning the details, don't look back.

Enjoy your trip!