Planning a trip

Personally I always book early. You might want to research the price fluctuations for a week and then the next week find it when it nears what you saw as the cheapest. That time of year, though, is certainly the low tourist times, so hotel wise you might be able to get a deal. Airlines wise book early, as it is a hub and business people and vacationers to other destinations are always going through O'Hare and it is one of the busiest airports. It used to be easy to get a flight, but I have noticed lately they have cut a lot of the flights they used to have and they have less delays, but barely enough flights to go with the passenger load. Also, Midway may be cheaper to fly to. Used to be an undesirable airport, but they really made it nicer, except the walk from the L to the terminal is forever!!! and at O'Hare it is like right there.