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I personally would go American because their miles are harder to get if you want to use it for personal award travel. If you need United miles, Chase credit cards transferred there.
United still makes sense unless you absolutely can't fly into EWR for some reason
There are hourly United flights from ORD to LGA and vice versa.
Depends on your travel priorities/goals. American usually has better rates for award flights using miles
United has a bigger presence at ORD, including to/from LGA and LAX, so it is probably a better bet to maximize options. Florida depends on where you're going, but it could give AA the lead.
Also think about your personal travel itineraries.