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You will have to deal with a couple of 'detours' along the route as there are sections of 66 that no longer exist and you'll have to take interstate highways for some of the distance. Parking an RV in Chicago proper will be a hassle. Can't help you there - sorry. But along the rest of the route, if you can't find an RV park or state/national park when you need to stop, local WalMart stores do allow RVs to use their parking lots for overnight. Plus, you get to stock up on supplies you may need.
You may also pass through some Native American reservation land. Most do not allow alcoholic beverages on the reservation. If you are taking some with you, be aware to seriously hide it in the vehicle until you have exited the reservation. We brought beer to a friend who lived on reservation land in New Mexico. We hid it in case we were stopped for anything by local law enforcement.
I recommend watching Billy Connolly's Route 66. He did the route from Chicago to Santa Monica on a motortrike. Not quite the same but his humor is wonderful and he went off the beaten path for certain sights. It's 4 parts and gives a good idea of the route. My husband's cousin and 3 others have done the round trip 3 times in a vintage corvette convertible.
Sorry I can't be of more help. I've only been on the route while traveling around Illinois and New Mexico. Good luck and enjoy the trip!
For bars in Chicago, there are a lot of choices. If you looking for regular bar with lots of different beer choices cheap, try Quenchers Saloon--they stock over 300 beers from around the world everyday. Beers run from $1 to $5 with most around $3.
If you want the real upscale spot, try The Underground. (Check it out on Foursquare for over 200 photos). This is the kind of place where you get Katy Perry appearing on a weekend while you and your date are drinking champagne and dancing (Katy headlined there back in 2010).
In Amarillo, I don't know where to go drink--but you just have to try "The Big Texan" (right on I-40, which is the originally US Route 66) to eat.
Nothing like it anywhere. This is the home of the gigantic steak with all the fixings.
[ 17-Jan-2013, at 15:43 by Calcruzer ]
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