Chicago-Portland drive in 3.5 days

I`m looking at a road trip from Chicago to Portland in 3.5 days, leaving Chicago after lunch on day one.
The "obvious" short route is to get to Minneapolis at the end of Day 0ne.
Day Two is Minneapolis to Billings, Montana.
Day Three is from Billings to Spokane, Washington.
Day Four is the home stretch into Portland, Oregon.
A longer, scenic route would go through Nebraska, then through Denver, CO and Salt Lake City. The last day would be a marathon from Salt Lake City to Portland. Is that even doable in 3.5 days with the same departure time? And can we make it to Lincoln or Omaha, Nebraska by 10 or 11 PM?
Thanks in advance for any advice, gld

Can anyone suggest how I can divvy up this drive? Leaving midday from Chicago, can I make it to Omaha comfortably by 10 or 11? Maybe stay in Salt Lake City on night #2, and Boise, Idaho on night #3 before taking the last leg into Portland on day #4? gld

Rock Springs Wy area. Omaha to Ogden (you dont actually touch SLC) is 900 miles or so

You may miss the divide if you`re looking the other way at the sign saying "Cont` Divide." The stretch from Ogden (SLC) to Pendleton is the best way to go north and west at the same time.
The mileage from Spokane to Portland is almost exactly the same as that from Boise to Portland ...
I drove from Colorado Springs to Spokane in without stopping at a steady 65 miles per hour with lots of coffee ... helps to have a sports car with a live steering wheel -- stops one from falling asleep.

You could get beyond Minneapolis on the first day. The northern route may be the fastest but I bet they are pretty close in distance and time.

least amount of time. Fine. Take the plane.
Drive through and experience a tiny part of this country? Go for it! Stop when you want - no Jack In the Box --strictly mom/pops beaneries. Talk to the lady at the hotel desk in O`Neill Nebraska who can prove she is an admiral in the Nebraska Navy, and takes delight in showing you the X-Rays of her hip.
What do you hear on AM radio in Chicago Sunday ams? Polkas. Week mornings = sow belly futures.
Promise yourself you`ll spend as little time on a goddam boring freeway as possible.
Go for it! At the worst you`ll still be reachable by AAA. Maybe 2 hours MAX away from the nearest Safeway/drug store/decent-adequate hotel. All freeways are essentially identical and miserable roputes. Go for the other roads. Jeeze! Go for it and stop worrying!
Do you simply want to get there or have a lifetime-memorable trip?

interstates being finished (it did take some long days tho). Unless you are making reservations in advance, do not plan on where you will stop each night. Allows you to stop at interesting places without worrying about where you have to be. Drive until you have had enough and stop. Chicago to Portland in 3.5 days is a very easy do without beating yourself to death.

How about the best stopping points from Portland to Chicago in 3 days?