Best way to book flights if unsure of date of travel?

I have always booked flights then cancelled it within 24 hours due to orbitz having the 24 hour courtesy cancellation policy. The thing about me is im always not 100 percent the exact date when i will be going somewhere and flying. And of course i dont want to pay a lot for airfare.
This is what i usually do. Say im planning to go around march. I would take a look at orbitz, look for the flight that doesn’t cost a lot then book it. However, within 24 hours, i would almost always cancel it and rebook it again on orbitz. Reason being if i do this, theres no fees to pay and if im not 100 percent sure. Thus i would do this over and over again every day until either the price of it goes higher or i know im 100 percent not going on that date. Or if the price of it is lower the next day, i would cancel it and rebook it. Or i would rebook it at another time etc if time/price is better.
I’m curious but does anyone here do this? The thing is if i know 100 percent im flying on a certain date, then its basically just looking at prices then booking it immediately. However, the issue here is if you book it then after 24 hours later, the prices are lower, then you can’t cancel it b/c there would be cancellation fee. Thus i basically look for a price i like that book it as long as its not very high. I also make sure to book 1 week in advance.
First off, im sure many ppl here do this right if they dont know a few weeks from now what day they want to go exactly? Another thing but do you book flights through sites like orbitz or expedia or do you prefer the exact airline such as american airline, jetblue etc?
The thing is i always sticked with orbitz b/c im always an undecided person and they have the 24 hour cancellation policy. Basically my last trip, i booked and cancelled 5 days in a row each within 24 hours and didn’t end up going because i had something else to do. But another time i did went, i always book and cancel few times.
Do other sites have the 24 hour courtesy cancel like orbitz? The reason why i never use expedia, kayak, hotwire, priceline, travelocity etc b/c im not sure about their policy. Do they have that 24 hour courtesy cancel like orbitz? What about directly through airline such as american airline, jetblue etc? I always hear its best if you book through expedia, orbitz that you should book directly with american airline, jetblue etc. Do you agree/disagree on this? Again i never do it b/c orbitz has that 24 hour courtesy cancel.
Also orbitz offers you travel insurance for a small amount but isn’t that useless? Im confused but are there any sites that allow u to cancel for free similar to orbitz? If so, any that allows more than 24 hours?
Thanks.

Why don’t you wait until you are sure to book the flight?

By law, all airfares sold in the US are cancellable within 24 hours of booking, with the exception of flights booked less than 7 days before the flight.

I also don’t understand why the OP is spending maybe 15 minutes a day every day for maybe a week futzing with airline tickets. What advantage does he think he’s getting?

United Airlines offers FareLock, where you pay a few bucks and they hold a ticket for three to seven days. If the fare goes down, you win, if the fare goes up, you’ve locked in your price, and if you decide you don’t want it you can cancel and you’ve only paid that fee.

And here’s a rundown in airline policies: http://thepointsguy.com/2014/03/american-airlines-ticket-hold-rule-change-no-24-hour-hold-for-flights-within-7-days/

This is your new best friend:

https://www.google.com/flights/

You can play around with dates, times, airlines, routes to your hearts content. Some people who shall remain nameless but whose user name starts with Bou and ends with ncer have been known to use this tool for mileage runs (cheap airfares for frequent flyer miles/status).

Regards,
-Bouncer-

That’s really useful.

Thank you, I built it all by hand. :smiley: I kid, I kid. There is one remarkably useful feature on it though. Pick any two cities and underneath the destination/date will be a little icon that looks like a bar chart. That’s the “lowest fares” icon.

Click that, and be amazed.
On Jan 1:
It costs 2000 bucks to fly from IAD (Washington DC/Dulles) to FRA (Frankfurt GER) on United round trip.
On Jan 2:
The same route costs 1500. $500 bucks for a one day difference.

You can find some goofy fares if you play with it and if you don’t care which airline.
The above route is $766 bucks round trip on Aeroflot on Jan 26.

Plus, of course, the map is fun to play with!

Regards,
-Bouncer-