I landed from Tampa at around 9:45AM, so first decided to head to the American Flagship Lounge. American operates out of Terminal 3 at O'Hare, while Cathay Pacific operates out of Terminal 5.
The lounges in Terminal 5 aren't exactly exciting, so I decided to first spend about an hour in the Flagship Lounge.
Then at around 11AM I took the train over to Terminal 5. This requires leaving security, so at around 11:15AM I was at Cathay Pacific's check-in counter.
I was quickly checked in and greeted by the station manager. My boarding pass was issued within a minute, at which point I was escorted through security.
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