Dean, Sam, and Charlie headed to the desk, cutting ahead of everyone trying to buy tickets or check in. They split up to find the person behind the desk who sold Castiel his ticket by showing his picture to make sure they were crashing the right flight.
Dean found the woman who sold Castiel his ticket to D.C.
"Yeah, I recognize him. His passport said 'Dean Winchester'" she said, looking him up on the passenger list.
"Perfect, thank you, uh, Amy…" Dean flashed his gorgeous smile. He wished he could stay and flirt but he had a spy to catch.
Well, there was no doubt Castiel was on this flight and took enough time to mess with Dean and clearly figured Dean would follow him. The flight was leaving in a half hour and had started boarding.
He must have underestimated how long it would take us to find him, he's probably just sitting on the plane with nowhere to go, Dean thought.
He grabbed Sam and Charlie and the chase was on. Pushing through all of the startled people, they stormed in the direction of the terminal Castiel would be at.
They flashed their CIA badges to pass security despite the yells from all of the travelers. It was a large airport and they passed a lot of people as they headed across the airport. Ten minutes later, they were there, catching their breath, at the desk of the terminal.
"We need to get on that plane," Dean demanded.
The flight attendant pursed his lips. "Really? What for?" he said snidely.
They all flashed their badges. "That's why, chuckles. Now, move," Dean said roughly.
They pushed past him and other confused flight attendants and they boarded the plane. It was set to take off in about twenty minutes now.
Scanning every face, Novak wasn't here. Dean got to the end of the plane and walked back down the aisle, re-checking everyone.
He shook his head when he got back to Sam and Charlie at the front of the plane and they got off. Back in the waiting area of the gate, a phone was ringing with an unfamiliar ringtone.
The three agents looked at each other. It didn't belong to any of them, but there was no one else around.
Dean reached in his leather jacket's pocket and pulled out a disposable phone he had never seen before. He looked up, shrugged, and flipped the phone open.
"Hello?"
"Dean, good to hear your voice," Castiel said. Dean could hear the smirk.
"Novak," Dean growled. Sam and Charlie raised their eyebrows.
"I'm guessing right now that you're standing in an empty terminal with your partners, wondering what flight I'm on if I'm not on the one to D.C and how you have this phone."
He nailed it but Dean wouldn't admit that so he said nothing.
"Well, I bought a ticket in your name to throw you off but I had another ticket. I am on that plane now so I'll have to hang up soon. Oh, and you walked past me in the airport about, oh…" Dean could tell he was sarcastically checking a watch, "seven minutes ago. Like I knew you would. So I planted a phone on you."
"Listen to me, you son of a bitch. I will still catch you, no matter what city you are flying to. I promise I am right behind you."
"And I will tell you again, handsome, you can try. I've always loved the chase," Castiel said and then hung up.
After relaying the conversation to his partners, they quickly headed to where security had their cameras.
They knew when he entered the airport and used the time to track him through the airport to find out that Castiel had gotten on a plane for Chicago. Checking the time at the gate as he boarded, they learned they flight should have just taken off.
"Can you check to see if the flight left?" Dean asked the security officer who had helped them.
He made a quick call and told them it was too late.
"All right, we need to get on the next flight out there. Let's go," Dean commanded and they headed back to the ticket counter.
"Dean, think about this for a second," Sam said as they walked.
"Think about it? We're running out of time. We need to get him," Dean snapped, not breaking his stride.
Charlie looked between the brothers, not sure what to say.
Sam could tell Dean wasn't going to give up and sighed.
"Lead the way."
Back at the ticket counter, Dean shoved past everyone again and bought three tickets to Chicago from Amy, who he would be sad to leave in San Francisco.
Landing in Chicago, the three of them headed to the security area of O'Hare International to try and find where Castiel was off to. Again, they found him getting into a cab and Charlie made a simple call to find where it took him.
"Thanks," Charlie said, hanging up. "He's headed to a hotel downtown, let's go! This is so exciting!"
Sam and Dean didn't quite share her sentiment but followed her outside to pile into a cab and follow Novak into downtown Chicago.
If Dean knew Castiel at all by now, he figured he would be in a ridiculously fancy hotel. Dean wasn't sure how he had the money but he figured it was through something illegal.
Once they finally arrived at the hotel, which was indeed fancy, they stormed to the front desk.
The trio confidently displayed their badges to the man behind the desk and the same picture of Castiel they showed at both airports.
Before answering, the man eyed Dean up and down, making him flustered to the bemusement of Sam and Charlie.
"Yes, I remember him. Such stunning eyes, this deep, deep, blue…" the man trailed off in thought.
"Great, but we need a room number. And a key," Sam said.
The concierge handed the key to Dean, saying "Room 334" with a wink.
In the elevator, Sam looked sideways at Dean with a small smile.
"Sam, we really don't have time for that, okay?"
"Time for what, to talk about that guy totally checking you out?" Charlie asked.
"Yes, that. We're in the same building as Castiel, who I've been after for three years," Dean rebutted.
"Yeah, because you have no game," Sam said with a full grin.
Dean shoved past them both as the elevator reached the third floor. He pulled his gun and reached Room 334, Sam and Charlie in tow with guns drawn as well.
They nodded and Dean readied the key, slid it in and out, and pushed the door open.
The room was dark as Dean stepped in but before Sam and Charlie could follow, the door slammed shut, the key still in Dean's hand.
"Hello, Dean."