The fact is that by adding Memphis to your itinerary, all of your previous plans and all the advice you've gotten so far are out the window. That's fine - it is the essence of RoadTripping to be able to design your route to suit your own objectives and to change your route at will, up to and beyond even the last minute. But realize that by heading first to Memphis, you'll probably be skipping the upper Mississippi and certainly foregoing the Ozarks. Instead, you'll be going through Lincoln country in Illinois, the mid-Mississippi, and Arkansas.
I-43/I-39 still offers the best option for getting around Chicago, then at Bloomington-Normal switch over to I-74/I-57 to continue southward through Illinois to I-55 in Missouri. Memphis to Dallas is then just a straight shot on I-40 to Little Rock and I-30 the rest of the way.
At well over 650 miles, there is simply no way that you can make it to Memphis in a single day. No matter what some software tells you. Remember that software makes no allowances for traffic, construction, gas or meal breaks, or even time to go to the bathroom. Software stupidly assumes that you can drive at or above the speed limit every second of every minute of every hour you're on the road. Sound realistic? In the real world, professional drivers are limited to no more than 600 miles a day because they with the inevitable fatigue that comes with driving that many hours/miles they become a danger to themselves and every one else on the road. And 'multiple drivers' don't really help since the more people in the car the more breaks you need and the longer they take, and no one gets meaningful rest while sitting in a cramped moving car.
Assuming you're still looking for some scenic 'detours', and are willing to take the time necessary for them, then you should be looking at routes such as US-45 through southern Illinois and Kentucky, and then US-51 through Tennessee to Memphis. In Arkansas US-79/US-370 would take you to Hot Springs before taking I-30 into Dallas. But you can't do both: Have a relaxing, scenic (and safe) drive, and get to Memphis in a day.
AZBuck