This is the way I have gone when I don't want to mess with all the Chicago traffic and all the tolls. I have taken this way with my TT and my semi many, many times...
I 90 to IL then pick up I 39 south to I 80 into I 94 east to highway 2 east pick up 20east all the way to the Ohio line 49 south to 6 east around Sandusky 2 east to Free I90 east through the rest of Ohio Through PA....I86 east (they have repaired most all of it ) through southern NY to Binghamton, NY I 81 north (or stay on 81 to NY17 TO I 84 EAST TO CT then I 90 mass pike ) to I 88 N/E to the NY Thruway and into the Mass Pike.
The only toll will be a small one south of Chicago on I 80 and from Schenectady, NY on the NY thruway and then the Mass pike. Sounds complicated but it is a good way to go to avoid tolls and traffic. I have been running across that way since the early 90's Some 2 lane some 4 lane.