Biased CO flyer here...

As a CO silver, you have a good chance for an upgrade on this route. If higher, I'd say your chances are excellent. No fare class restriction on upgrades.

I don't know if CLE is a connection option. If it is, I'd go for that - you're competing with fewer elites for the upgrade on the second segment.

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"I will not be pushed, filed, stamped, indexed, briefed, debriefed or numbered. My life is my own."