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Do you have to go to Chicago? It's awesome, don't get me wrong, but it puts you in a bad spot. That area of the country is the least interesting in my opinion (I would know because I grew up there), and it's a 10-15 hour drive to the more interesting parts of the country.
Especially since it sounds like you're interested in National Parks, I would fly into: Denver, San Francisco, or Seattle and start from there.
Quoted from genex:If you are looking to stay at AirBnB's while you are traveling many people have pins (my listing includes my Shadow) so you can stay in places with pinball too if you like (and probably meet neat pinheads). I always get a kick checking the last score played on the machine after a visitor stays at my place - and checking to see if they put their initials up
My AirBnb space has 5 arcade games (Turbo, Frogger, Joust, Battlezone, Ms Pac-man) and 3 pins (Breakshot, Twilight Zone, High Speed) at the moment.
It would be cool if we could compile a master list somewhere - so road-tripping pinheads would know where to stay.
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Boulder, CO