I towed a fully loaded 12'x6' U-Haul from Schererville, IN to Naperville, IL helping my brother move. That was fun on I-355. First of all, it's got some of the most expensive tolls around and I had 2 more axles. I want to say I paid like $4.20 for the first toll on there and a dollar something for every toll after that. The Jeep performed perfectly though. I didn't overheat and it didn't even struggle. That was before I had my Aussie in the rear though. I don't think I'd do that again with the Aussie in there. I think I'd end up snapping an axle shaft trying to back into a driveway.
Yikes I know those tolls and they suck. I love the new leg of 355 to I80 but avoid it if I can due to those tolls. They raise them every year and I heard another hike is coming for 2014. IL sux.
98 5.9 Limited - IRO 3.5", IRO short arms track bars Bilsteins, Addco, JK wheels, 255-75/17 BFG, Magnaflow, Flowmaster
04 Limited 4.7H.O QD, UC+BB, Bilsteins, 245/75-16 Duratracs Addco sway bar