Grand Theft Auto IV

Instead of trying in free-roam, do it during Mori's 2nd mission. It starts you way higher then the max you can go in a helicopter, so even if you pull it lets say 4 seconds before you hit the ground, you will easily get it.

The mission is called "This Ain't Checkers" for anyone wondering.

Make sure u put the parachute on your back before flying up in the helicopter.
Get a helicopter and fly up as high as you can, free fall out until you are 1-2secs above the ground deploy parachute and land without dyeing. Achievement will unlock. You unlock the parachute after finishing Yusuf's 2nd mission.

For this achievement you have to fly as high as possible and then freefall the longest possible time to open your parachute in the last moment and land safe.

This achievement will become obtainable when you have access to the parachute, after the mission "High Dive".

Make sure you have your parachute on and enter any helicopter, you will find various within Liberty City.

This is a handy map for locations in Liberty City:
http://grandtheftauto.ign.com/maps/1/Liberty-City-Map

Then fly as high as possible and watch your altimeter on the radar, also be sure to fly over water, just to be on the safe side.

I used Yusuf's Buzzard, this one will be unlocked after you finished the storyline. There is also a parachute nearby.

The most difficult thing is the correct timing.
Since I just got this achievement, I used a stopwatch to get the exact time.

The moment you press "Y" to jump out of the helicopter, start your stopwatch. Then only look at that stopwatch and press "A" after 14,9 seconds. Then you should get the achievement when landing in the water.

I did it nearby where the buzzard spawns but it should work at any place if you fly over water.

I hope I could help you with this achievement :D.
Feel free to give your comment if it works or not.

You won't be able to attempt this achievement until you have completed the storyline mission "High Dive". Once you have done this you will gain access to the parachute by calling up Armando and purchasing it from the back of his car (along with numerous other weapons). Once you have one head on over to Fishmarket South and head to The Higgins Helitours helipad. Now "Borrow" one of the helicopters and fly as high as you can. When you get to the higest point achievable - you will be able to tell by the height guage on the map - jump out and freefall. Now you need to fall until you are just a few seconds away from the ground. Once you feel you have fallen far enough you need to release your chute (pressing A) and if you have timed it right you will land safely and also unlock the achievement. I would advise you to do this over water in case your timing is slightly out.

If you've unlocked Yusef's Buzzard you can use it to work on this achievement. A parachute spawns right by it so if you pick it up you'll always have the parachute equipped when you start up the helicopter (you can tell it's equipped because Luis will be wearing it as you lift off the ground. If it isn't equipped before you jump you'll fall to your death).

Take the Buzzard as high as you can go and slightly out over the water. You'll know you're as high up as you can get when the altimeter is all the way at the top and the camera view of the helicopter starts to change and pan overhead. Jump out, freefall as long as you can, and pull the parachute at the last second. It should inflate and slow your fall but you shouldn't have time to glide.

If you jump over the water you're far less likely to die if you don't get the timing quite right, and if you don't go very far from where you got the helicopter then it's a short swim back. The parachute and Buzzard will have respawned and you can try it again.

This achievement is fairly easy to earn, and all you need to earn it is a helicopter and parachute. Here is a video guide I made for this achievement:

I keep seeing solutions saying that you need to wait until Yusuf's 2nd mission. This is not quite correct.

You are able to use cheat codes by entering the following numbers on your phone ( to access the keypad):

Parachute: 3595557272.
Helicopter: 3595552899.

I recommend flying over Middle Park in order to avoid the skyscrapers.

Equip the parachute by scrolling through your weapons & press to equip. Then, get in the Heli and fly as possible. Next, jump out and when you have a couple of seconds left, press to open the parachute.
If you get your timings wrong, use the cheats again by scrolling through the phone menu to Cheats as all cheats are saved to the phone.

Codes found on Cheat Code Central
Video courtesy of YouTube user GTA Series Videos