Outbound to Chicago DuPage.
I did this trip by myself.
From TOIdentifier Hours Altitudes Conditions of flight
Seattle Twin Falls, IDKTWF 3.4 13,000 IFR
Twin Falls Rawlins, WYKRWL 2.6 11,500 - 17,500 VFRSpent the night here
Rawlins Sioux City, IAKSUX 3.7 9,500 VFR
Sioux City, IA West Chicago/DuPage, ILKDPA 2.8 7,500 mostly IFR
Total: 12.5 hours over two days

The return trip home.
My friend Jan came along on this segment.
From TOIdentifier Hours Altitudes Conditions of flight
Chicago Rochester, MNKRST 2.0 6,500 VFRSpent the night here
Rochester Rapid City, SDKRAP 4.1 10,500 VFR
Rapid City Billings, MTKBIL 2.6 14,500 VFRSpent the night here
Billings Spokane, WAKGEG 3.3 14,500 VFR
Spokane Seattle Boeing Field, WAKBFI 2.0 12,000 IFR
Total: 14.0 hours over three days

Tips for when I do it again...