Re: US trip (next July)
If you drive where possible and fly where you can't drive...
-NY, Boston, Philly is manageable in 4 days, but time your travel times to avoid I95 and city rush hours.
-Maryland to Florida in 5 days is also pretty easy by car... but Texas will require a flight... as will the return to Chicago... and the Chicago to NV hop (unless you want to spend your entire vacation in a car).
-Vegas to LA to San Diego is a nice drive (6 hours maybe), but SD to Frisco is a long haul (8 hours in perfect traffic... probably closer to 10 or 11 hours in real life) so probably a flight there would save a lot of time.
-I've never been on the run from Frisco to Seattle or Vancouver so I can't help you there... other that to say it's also quite a ways.
You COULD fly from Chicago to Salt Lake and drive from there to Vegas/LA/SD - it's a full days drive though... add Denver in and you're looking at an easy (and very cool) 8 hour mountain drive from Denver to SLC on one day and a full (11-12 hour) second day of driving to get to SD.
There's hiking all over the place... but you'll probably not want to hike in the south or west at low altitudes in July, HOT!
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