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If we're limited to freeway driving, I-26 north out of Asheville takes the cake for me in the east.  Of course out west there are many options.

One of the most boring is I-75 south of Macon.  At least it's six lanes.

I-75 at the TN/KY state line (in TN actually) is interesting.  It's one of the last segments finished and goes up, runs along a ridge at about 2,000 feet, then comes down (with a bit of a dip in the middle as it crosses to a second ridge).  The WV Turnpike is nice in spots, as is the PA pike.

My stepson drove us back from Orlando to ATL last year.  He has a heavy foot.  We averaged 97 mph (aside from one stop).  He's a good driver fortunately.  But we didn't get passed except once.

When speed limits were 55 mph on Interstates, I had a CB, which mostly worked.

I agree on Illinois the long way being a boring drive. 

29 in North Dakota (and 94 between Rothsay, MN and western Jamestown), between Fargo and the Canadian border post at Pembina, feels like you can get out and walk faster even if going 80+.

65 between the Chicago burbs and Indianapolis is not only flat and boring but only 2 lanes and in terrible shape. Clearly none of the money from the toll road sale went there. 

For non freeway driving, the winner has to be the provincial roads of rural Saskatchewan between Regina and the coal country of Estevan/ North Portal. 

I agree on Illinois the long way being a boring drive.

29 in North Dakota (and 94 between Rothsay, MN and western Jamestown), between Fargo and the Canadian border post at Pembina, feels like you can get out and walk faster even if going 80+.

65 between the Chicago burbs and Indianapolis is not only flat and boring but only 2 lanes and in terrible shape. Clearly none of the money from the toll road sale went there.

For non freeway driving, the winner has to be the provincial roads of rural Saskatchewan between Regina and the coal country of Estevan/ North Portal.

For us we would take 75 North, then 24, then 55 to 355. Terribly boring drive except for small stretches in GA, TN and KY. Feels like a week of driving.

When we went up last year for a month, we flew and rented a car. 

It was about the same cost as driving (gas was up) and using hotels along the way. We do three days.

Car was $250/week and flights were free.

My company has a deal with Enterprise. It's pretty damn good.