Some brief notes:
RailsConf was fantastic. I expect next year to be much crazier, but we'll hope it keeps its class. The current community is so bright as a collective whole.
Chicago's "L" system is really good. People who live there often don't realize how easy it is to get around the city.
Chicagoland's Metra trains are also very nice. No complaints there, though I wonder if they could add wi-fi...
I took an Amtrak train from Chicago to Washington, D.C. which arrived 7 hours late. I do love Amtrak, but they don't make it easy. We really need to make rails service more of a priority in this country.
D.C.'s Metro system is surprisingly nice. Very clean and few advertisements. July 4th found it body-to-body after the fireworks, but it could have been much worse.
The airline industry, while much quicker, is completely backwards. I should be able to pick and choose flights (find a cheap one from D.C. to chicago, then find one to Grand Rapids) but instead, am forced to pick one airline for the entire trip, limiting my options. It is ridiculous that a ticket from D.C. through Chicago to Grand Rapids is cheaper than a ticket from Chicago to Grand Rapids (on the same flight) alone.