Roadtrip Planner Need Help Planning A Roadtrip! Tips/advice?

Need help planning a roadtrip! Tips/advice? - roadtrip planner

My 4 best friends and I are considering a road trip from Toronto to Chicago for 4 days in August (for Lollapalooza). I was wondering if anyone has tips to save money on road trips, and if you know a site that could be used to find out how everything costs, etc. as a whole? Almost like an online road trip planner? Haha

And nobody has been before Lollapalooza? All information about hotels, or by how much the cost for the festival?

Thank you!