Similar comments to what has already been expressed. It is about 1000 miles from Chicago to Denver. Making some assumptions about your starting point and route. To get to Oregon you would probably go further north and cross the mountains in Wyoming or Montana. But figure roughly 1000 to 1200 miles to the Rockies. Assuming you ride 70 miles per day you will get to the Rockies in 2.5 weeks. Roughly. Depending on when you start in April, you will get to the Rockies between mid April and mid May.
I rode Pedal the Peaks in mid June 2003. We crossed Rocky Mt. National Park and Rabbit Ears Pass during the week. It was cold and windy at the top of the passes. Snow on the ground but none falling from the sky. With gloves, a balaclava, wind vest, short sleeve jersey and winter jersey, tights, and wool socks, I was comfortable. I'd suggest this as the very minimum of clothes for mountain riding any time of year.
I also toured in the Rockies of Colorado in early September 1997. Red Mountain Pass, Lake City, Gunnison, Durango, Ouray area. It was cold and rainy at the top of some of the passes at that time of year.
You can cross the mountains in one day of riding. Or two depending on whether there are back to back ridges. The weather is only bad at the top. In the valleys on either side it will not be a blizzard and below freezing. So at worst you will only be exposed to the bad weather for the few hours near the top. And always remember if you are riding up and it starts to get bad, just turn around and coast back down to the warmer valley in 30 minutes. The weather is warmer and nicer at the bottom of the climb. Then find a different route or wait until the weather is good for crossing the mountains.
This message was edited by RussellSeaton on 2-17-05 @ 7:32 PM