Who knows how to get the cheapest flights? When to buy?

Question 1: Should I go round trip or buy two one way flights?

Which is cheaper?

@Chim_Richalds said:

Who knows how to get the cheapest flights? When to buy?

Question 1: Should I go round trip or buy two one way flights?

Which is cheaper?

Here's a lengthy "teach a man to fish paragraph" but if you'd like to give me dates and cities involved ill check it out for you.
Points:
I'm using points for NYE it'll cost 40,000 miles but I get to travel first class from San Diego TO New YORK on the way back it's cattle car. Whether a hotel or a plane ticket you want the points to get you as much as possible obviously, 40,000 pts for a $1700 flight is decent, like 2.5¢ on the dollar, it varies but those are American Express points transferred over. Point is if the flight is $300 don't waste your points.

Ok, so check your sites Travelocity, Priceline, Kayak. Punch in your origin and destination, as well as dates and times; if podsible be flexible; TUESDAY is the cheapest day to fly as a rule. Airlines with the flights meeting your itinersry will pop up on each of the travel sites, note the prices and then go directky to the airline website and double check before making a bid or purchase because sometimes they'll have a better deal.

Round trip is usually cheaper unless you get a "deal" places like travel zoo have specials they run weekly, if you punch in travel zoo several similar sights will come up. They are worth looking into as wel but more difficult when you have specific destinations and time frames.

Generally the closer you get to your departure the cheaper potentially you could get it on Priceline. That is a double edged sword though, because if you wait the plane could book, or it could start filling up forcing you to buy a ticket at cost and within 2 weeks of departure prices are sky high. (Example: I used to fly from pit to Philly 6 times a year, a secretary that made the reservations retired and no one picked up the slack, I still had to go. The normally $350 ticket RT cost $1600 RT; be careful.

Bidding on Priceline works, you can save some money. Be careful with baggage fees, taxes, and service fees they can add up, without baggage I believe domestically fees are around $50-$70. Be prepared to buy the ticket/a if you use Priceline. Insurance is worth it in some cases like NYE but be sure of what the traveler insurance covers. 20% less than the posted price is a solid bid on Priceline, and only when the plane is packed would you not score the discount.

If its for NYE I'd book immediately. If its for vacation or business that is not pressing then I'd recommend checking out all the websites I mentioned to include the airlines. Try the flight a few different ways, from different departures. Try to leave on Tuesday.

I did this for a living for 10+ years, been travelling all my life. If you need help, feel free to PM

466$ on southwest rt out of Abq. No bag fees. Gonna see the whole run. Yeah super pumped.
I heard that 2am on Wednesdays is a good time to buy a flight. Prob just rumor but worth a shot.
Used airbnb to score a 3bdrm loft in bklyn for 200$ a night. Dope place in nice area. Again super pumped!

People spend a lot of money to see Phish. They'd better f***ing appreciate it and blow our doors off this year....

Yeah man, it's all about shopping and watching the prices. I just bought a ticket to Rwanda for VERY cheap because people were watching the "market".

It also depends on the day of the week. Each day usually comes with a different price tag.