Hello and welcome to the RTA forums !

On long trips like this it's important to pace yourself for both comfort and safety issues. We generally recommend travelling between 500-600 miles per day maximum for multi day trips. [9-10 hours] That's on Intertsate and major Highways with time for basic stops, but with no major sight seeing, plus weather can hamper your progress and that should be planned for. The main thing is that you should have no real need to book lodgings in advance, so you could just roll with it and see how your days unfold while trying to keep to a rough schedule on when you will be arriving at your friends/family homes. For example, from Seattle to Chicago you should allow for a minimum of 3 overnight stops if your main focus is just in the getting there. You could look for places that interest you to visit and/or to stop for the night and repeat throughout your trip.

With a trip that is likely to cover 9000 plus miles with lots of little detours you can expect it to be 16 'or so' days dedicated to driving. Whereas that leaves you with 10 days to spend however you want, it's not actually enough time to spend a full day at each of the places you wish to visit with family and friends.

Your trip is certainly doable, but there is a lot to cover. As long as you have no plans for 'a few days here' and 'a few days there' you should be fine.