Henderson had never expected that CTU wouldn't eventually find him. He knows how it works, knows that other than a few basic steps there's little he can do to evade detection once CTU starts pursuing certain threads. The trick isn't to try not to be found out, it's to get out of whatever trouble you find yourself in when you are. Always have insurance.
The only thing he'd gotten wrong was the timing, but then that wasn't his fault. There wasn't supposed to have been a nuclear bomb detonation, making it impossible for him to get to his insurance; Caiti was supposed to have been his leverage to cover up his involvement. Now he has to prioritize. Better to get the evidence he can use to save his skin and avoid capture by CTU just using his wits; the genie's out of the bottle already anyway, through some means he hadn't expected.
He taps a key on the keyboard, changing the view from the cameras in his and Miriam's house. Not surprising that Jack's shown up in person to search the place for him, though he'd made allowances to his plan just in case. This makes it easier, however. CTU agents scour the house, but he knows they won't find much that's incriminating; he's been too careful to leave many clues, though there are some if they look hard enough.
That's none of his concern now, though. Time to get moving, to put his plan into motion. He has to move if he's going to continue to stay a few steps ahead.
Walking over to Caiti's room, he taps on the door once, before opening it, levelling a gun at her in case she needs the extra encouragement. "I'm going to call your sister soon, and you'll be with her not long from now as long as you and she both do what I say," he says sternly. "Put your hands behind your back, we're going for a little drive."
The private airfield is the perfect location for a meet. The buildings spaced distantly enough to prevent others from hearing anything suspicious, its location near a number of highways, leading to a selection of escape routes. Omicron's ownership of a hangar for the company jet makes it convenient; no worries about creating an alias or lying his way onto the property. Hell, he even has a key for the hangar.
Driving up to the hangar, he pulls Caiti out of the backseat, dragging her inside the hangar and over to a small office. "Sit," he says, pointing to the chair. She obeys without a sound, and he pulls his cellphone out of his pocket, dialling Chris Chappelle's cellphone. For her sister's sake, she'd better have it turned on.