Don't know what the deal with the hate on Logan is. Not the fanciest airport but top 5 worst? Come on. Orlando's definitely gorgeous though.
IAH has the smallest passenger pickup area I have ever seen at any airport. Some times it takes my parents 30 minutes of waiting in a car line to finally get there. Other airports usually have a very very long pickup area which helps disperse the cars a little bit. You also have to walk a mile to get to the baggage area from Terminal E.
1: Only 3 cities in the U.S. are larger than Houston. Believe you me, IAH blows away a boatload of airports serving smaller populations. 2: The local population base doesn't necessarily indicate the number of travelers through an airport.
My mom just retired after 30+ years at British Airways at IAH, and I've grown up with that airport. It always amazes me when I fly out of IAH just how much it has grown, and Houston with it. But yeah, the lack of any public transportation from IAH to the city center makes zero sense to me.
That's why I like Chicago's airports. Sure, your flight occasionally might be delayed, but at least there is mass transit to and from both airports.