Helpful Americans Please:)

[LarsMac]

From what I am reading, the second leg of this trip will occur some time in the September-November time frame.

This would make the southern route much more favorable.
And late september, early October is a GREAT time to be going through southern Colorado, Northern New Mexico.
After Durango, I recommend running south into Joser's home state, and checking out Taos and Santa Fe, and hooking up with Route 66 from there.

Weather is "usually" decent that time of year, but, anything can happen.

[LarsMac]

Originally Posted by Centech

Drive to the airport in Salt Lake City.. Fly to O'hare.. Drive to downtown Chicago.
...
.

Nah, take the train.

[Hurrikane]

Thanks so much to everyone for the help; we've kinda settled on a route from Salt Lake City that takes in the Grand Canyon (Flagstaff kinda direction), passing through Amarillo, TX then striking it towards Chicago, hopefully bumping into Route 66 as we go.

Another Query, this time to New Yorkers;

We will end our trip in NY for the New Year's celebrations in Times Square. We will be driving from Boston; New York is HUGE to us... where best to head for to base ourselves for a couple of weeks, sell the car, and get into the City easy enough for New Year's eve? Talking cheap motels/hotels/rooms but ok neighborhood.

Thanks again,

Hurrikane

[LarsMac]

I am not a New Yorker, but for a couple of years was working in and around the city.
"cheap hotels" in New York are NOT usually in nice neighborhoods, but if you explore the railway maps a bit , you can find towns along the railway that have mid-level hotel/motels close enough to the rail lines to get in and out of NYC easily. Also north of the city in NEW York is a good place to look.

I would suggest you move fairly quickly on securing lodging.
You may already have to look pretty far afield to find rooms for that time-frame.