When traveling North from DFW, Texas, I like to use I 35 North, I 30 NE, I 40 North, I 55 North, to US 51 North, to Bloomington, then I 39/90 on up into WI. Very pleasant drive and no large cities.
If you think Chicago's tolls are expensive. Stay away from Texas and the NTTA. A three axle trailer will cost you four (4) time your TV only toll using the "TollTag", and 7.3 times the "ZipCash" (no toll tag) rate. The NTTA requires the TT "TollTag" to be in the TV glove compartment , not displayed on the TT upper front window, even though, it is a mini-transponder. On another note, it was cheeper to join the Denver ExpressPass and give them a $40 deposit than not doing so. In two trips I saved the deposit and some more. But, they just keep the deposit with no refund option. Not as bad as Texas. I have complained to NTTA, but have not received an answer. Unfortunately, All these toll authorities are not connected electronically. It would sure make travel around the country easier if they were.
Maybe someday they will all join together in the the electronic world.