I don't know if it breaks any actual grammatical rules, but an English speaker would never say this. Only the first 'although' is needed:
Although the roads were clear, the weather was good, and he set off an hour early, John was still late for work.
If there are two sets of reasons caused by different things, you could break up the second group with 'and though':
Although John's car was clean, well kept, and fast; and though the roads were clear, clean, and wide, John was still late for work.
The first group of conditions are why his car should be able to get him there, and the second set of conditions are why the roads shouldn't have slowed him down.