10.5K AA miles x 5 pax (Status: EXP)
AA CLE-ORD 8:13PM-8:55PM RJ145
AA ORD-MCI 10:10PM-11:42PM A320
Pros: Shorter travel time.
Cons: Riskier weather in the winter in ORD, RJ145 flight with no WiFi or E+, AA reliability.
10K UA miles x 5 pax (Status: GS)
UA CLE-IAH 6:35pm-8:50pm 737-700
UA IAH-MCI 9:35pm-11:35pm RJ175
Pros: GS protections, better planes
Cons: Long flight time, short connection