Yeah, the only way Dulles makes sense is if they expect to code share with United.

Midway is a somewhat more convenient airport to fly into and out of, but O’Hare isn’t awful. It’s also a United hub.
 
FWIW an Uber from LGA to Williamsburg cost me US$45 on my last trip.
Ah - only a 10 to 15 minute ride if there's no traffic. With a single expressway one way to another. I'll have to try LaGuardia one day - though I'd much sooner not fly Air Canada.

Ouch - CAN$63 for a 15-minute uber ride. Makes Toronto look cheap!
 
With limited transit, I prefer Newark. Easy to get to Midtown from there. How good is the bus from LGA?
The Q70 to Jackson Heights Station is generally pretty good, combined with the E or F into Manhattan it can be faster than NJ Transit from Newark (and much cheaper, and you don't have to potentially wait an hour for a train). If you aren't intimidated by using buses in New York it's the easiest of the 3 airports to get to on transit.
 

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