Is O Hare airport or Midway airport in Chicago better? Which is the better option to fly out of? Does it even matter?

If you plan on flying Southwest, your only option is Midway. Otherwise, you'll likely be flying into O'hare.
I've always enjoyed O'hare and since I don't fly Southwest, I usually fly into O'hare.
I love airports in general so I've certainly been to Midway several times but O'hare has more of everything

I always fly out of O'Hare.
Midway is too far from us and I don't like driving in the area it is in.
O'Hare is much easier to get into and out of.

ORD by far
Why ?
BC MDW has short runways and is in the middle of a neighborhood. In the event of a rejected take off or a rejected landing your airplane may run out of runway and wind up in a 12 flat
MDW Runways
13 C/31C>6522'
4R/22L>6445'
4L/22R>5507'
13L/31R>5141'
ORD runways
10L/28R>13000'
10C/28C>10801'
14L/22R>10005'
14R/32L9686'
4R/22L>8075'
9R/27L>7967'
4L/22R>7500'
9R/27L>7500'

O'hare has a lot more flights going to many more places.

O'Hare, by far.

Better for what?
If you want to fly halfway around the world, your only option is O'Hare.
If you want a cheap flight on Southwest, they only fly from Midway.
If you are flying somewhere in the US, I would look up flights for both airports and pick the flight that best suits me.