Advice on Toll Roads and Road Trips

[Shameless Lefty Hack]

WisDOT might know.

Having driven Chicago <---> the east coast many times at this point, I can strongly recommend avoiding tolls at least in Indiana, Ohio, and Chicagoland. The tollways don't save you much time at all (the possible exception in your case maybe being Rte 94, depending on where you're coming from in WI.) If your destination is NYC you're unfortunately going to have to be paying some tolls, though.

[Shameless Lefty Hack]

Looked into it a bit. Looks like I-Pass might be your best bet, which you can find here.

[Shameless Lefty Hack]

BTW, I 95 is probably the best way to get through the NYC/CT area....although there's no trucks allowed on the Merritt Parkway (route 15), that road can get quite congested, and it doesn't have exits in every town.  Also....avoid route 8 if at all possible, it's quite the narrow and busy road. 

In my experience it's a coin flip between going 20 mph on Merritt vs going 20 mph on 95. But I think Arch's destination is NYC, so (thankfully!) they don't have to go through any of that.