[Butch Cassidy Slept Here]

Conn. to Madison, Wisc: AMTRAK has one-train service to Chicago from Springfield, Mass. and Penn Station, Manhattan. Drive time (rental car) from Chicago is under 3 hours. Total nights "on the road:" 2 (one on the train, one following arrival in Chicago.) Sleeping cars are available on the train.

With regard to air travel: Nowdays it's unrealistic to think you can travel from point A to point B and be able to make a meeting, wedding, funeral, etc. the morning of the day after your arrival. There has been more than one post on this board about someone leaving on a cruise, but waiting until the day before the sailing to fly to the port. What do you think happened? As you found-out, all too often, the plane gets you there no faster than the train. Airports at any major city in the US are running on "overload" in terms of the number of flights that can be handled. So anything less than perfect weather, effectively, shuts everything down.