When I think of all the trips we made from WI to PA without an I-Pass, I want to smack myself in the head. I never knew that using the I-Pass cuts the tolls in half (at least the IL ones - it's been so long since we traveled that I don't remember whether that was true for all the toll roads.) And now I know to avoid the Mass. Turnpike.
Unless you have an ezpass! Then it's fine! Random statement: There's a bridge from Indiana to Louisville that costs money. It's the only toll near me. But, if you have an ezpass, it's half price. The IN ezpass doesn't give a discount, and it doesn't save you money. So, I got one from a different state (totally allowed, I read the rules!) because it has no maintenance fee! I plan on making trips around the northeast, so I know having an ezpass with be handy. We didn't need it in the West, because only California has tolls, and you can avoid them easily.
I LOVE road trips!!! So fun. I've made several cross-country trips, but all along the southern part of the country or up the western states. Still on my bucket list is to drive the Lewis & Clark route and the Natchez Trace. I don't see anyone gave you any ideas on the stint between SF & SLC. If you've never been to Lake Tahoe I highly recommend it. I can't wait to see photos/LOs of your trip when you've returned!
Driving up Lake Shore Drive is really cool. I'm not sure how much hotels will be as they said last night on the news that hotels are at 40% occupancy. I think what gets you in the city is paying to park your car as well. You can always stay in a suburb on the metra line and train in for the day. Coming into downtown, you'll be able to hit the main attractions from there. I guess my question is, do you want to see more of the typical Chicago touristy stuff or see the neighborhoods? Oh... one option if you wanted to drive in for the day would be to go up Lake Shore Drive to Fullerton and go the Lincoln Park Zoo. It's probably easiest to just pay to park in the zoo's lot. It's a good spot to wander from though. The zoo is free and you're in the middle of Lincoln Park so you can wander through the gardens and the conservatory. South Pond and North Pond have very cool skyline views (South Pond has a nature boardwalk that's really pretty) and there's a pedestrian bridge across Lake Shore Drive to the beach. So many cool photo ops!! One of our favorites is the South Pond Pavilion...