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Help planning a trip taking in route 66

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I was wondering if anyone had any advice on a trip I'm planning for myself and my friend this September. I'm hoping to get my head around the timeframes for driving along route 66 to see if we can fit it in with some birthday celebrations.

We have three weeks where we hopefully will;
-fly out to San Francisco from London
-Take in Route 66 while staying in Las Vegas long enough to celebrate her 30th for a few days.
-Fly home from Chicago

We'll be hiring a car so I guess I need to know how long does it take to drive the Route including stop overs and is it at all feasible with our timeframe?

Any help or a push in the right direction will be much appreciated!

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