Cyber Monday

I'm a bit skeptical that "cyber monday" is a thing at all, for the purposes of booking flights.

I suspect you would do just as well or better if you do what most folks here recommend: start early (at least 6+ months ahead), get a sense for the price range within which fares tend to fluctuate, simply monitor prices on a regular basis, and when you see a fare you can live with, jump on it. I don't believe there's any magic shortcuts.

For bookings to Hawaii in February, I think it's already quite late in the game.
For Italy in May, I'd be watching fares every day right now.

February is definitely high season in Hawaii. I completely agree with David’s assessments that you are unlikely to find any Cyber Monday deals on that flight, and that it is already pretty late to book.

hey hey shusak
are you asking for airfare for both of your trips? where are you flying from and what island are you going to? what is your budget?
i agree with Lola about hawaii and high season. i'm from the big island, lots of people getting out of the cold weather to enjoy the islands.
like david says about "cyber monday" have no clue what kind of deals will be out there and if any. selections may vary with many restrictions. i use kayak to look then go to either hawaiian or alaska and what's offered. I don't worry about places to stay, my family is there, but hotels/condos/apts may have slim pickens and high season rates, rental cars same thing. i've been there when there was no cars available in kona, people finding a way to hilo with few rentals there. good luck in your researching.
aloha

Southwest recently started flying to Hawaii. You should check them out now! I would not wait for Cyber Monday.

We go to Hawaii every year. I usually buy my tickets 9-10 months in advance.

I got an e-mail from Hawaiian Airlines today about a fare sale they are now having. Check it out. aloha charlie

It seems Hawaii flights were particularly affected by the grounding of the 737 Max jets. So, there may be less competition to Hawaii than before. Yet another factor arguing against waiting for a "sale" on this flight.

I have never seen a correlation between cyber Monday and airfares especially to destinations at peak & shoulder seasons.

Thank you all for the information.

As soon as we decide if we are doing the Big Island or Kauai as our second stop after Oahu, I will get flights booked.

I just bought round trip tickets to Milan from Miami for $575 for late May returning first week in June. On American. It is a direct flight. My kids saved a few bucks flying through London. I found there was a big difference in price between Friday and Saturday night with Saturday being more expensive.

I don’t think tickets much cheaper than this so I would definitely look seriously for tickets to Italy now for May.

Not sure where you’re located but there were good deals yesterday to Hawaii out of several American cities.

I pay for a subscription to a service called Scott’s Cheap Flights. I get alerts whenever there are deals out of the cities I have selected to get notices for. It’s saved us a lot of money. I highly recommend it if you travel very often.

Wouldn't it be great if it were that easy to predict airfares reliably? I can say that for the last three years we caught some good fare sales on Delta to Europe that popped up just before Thanksgiving, and were gone in a few days. I think the strategy is to know what the fares for your travel dates in May are right now, and keep a daily watch. If you see a significant dip, jump on it.

For flights to Europe, I absolutely belong to the School of Stan (above)

You can check on Hawaii deals at any time. I used to live on island and go back and forth quite often. If you can snag a RT under $400 take it now. As for Cyber Monday for Black Friday airfare deals, those do exist and vary by airline. Some airlines do a 12 days of Holidays special in December.

I saw some really great one last year that would've worked if i were taking tours for Spring/Summer, and really wish I had booked my Japan flight for cherry blossom season when those deals came out for Black Friday/Cyber Monday. You can set alerts now on various sites that can track increase or decrease in fares. For example, Google flights emailed me today that my RT flight for the RS Andalucia trip I am taking in June the cost went from $1300+ down to $783 RT. flying economy. I have since reset my alert to premium economy to see what comes up in the future. Happy Fare Hunting!