This one's quite easy. When you get the ability to cruise with all characters and have met them all, simply phone them all up, then when you're in a vehicle together, get a wanted level of 3 stars or more (to make sure you don't lose them easily), then spend over three minutes with the wanted level, but don't die or get busted.
To do it, drive to Ammu-Nation and put on a suit of Super Heavy Armor. Weapons don't really matter, but it's nice to have them to help.
Call Michael and Trevor on your phone under Contacts, then quickly pick each of them up, using the icons on your map to find them. Don't take too long to pick them up, or their icons disappear and they'll refuse to answer your calls for a while. Use your horn to attract their attention when nearby.
Once you have your crew together, head to Los Santos Customs. Upgrade your Vehicle Armor and Engine. Drive to Los Santos airport and drive through the main hangar gate. Drive your car out on to the airfield. This will instantly trigger a three-star Wanted Level. Now simply circle the airfield for three minutes. If the police lose track of you, drive into their cone of vision to maintain the Wanted level.
A walkthrough video kindly provided by NEO182 is below, from his randomchievos channel on YouTube.
NOTE: There's a strange phenomenon happening just lately with the Achievement system on the Xbox One. Achievements aren't popping visibly or audibly, but they do. Your console has to be connected to Live, so if they don't pop, check your Internet connection, and the Xbox Live status page at http://support.xbox.com/en-US/xbox-live-status
They DO pop correctly, as I obtained them on the 360 version.