I’m leaving for New York early in the am. I am planning to drive straight through, I get it done in about 11 hours. But, I do plan to stop for dinner on the way there and breakfast or lunch on the way back.
On the way to Chicago get off at the Middlebury (Indiana) exit, turn right and head south. You will travel 5-7 miles through the town of Middlebury yntil you reach US 20. Turn right and go about 2 miles, as you come up the top of the hill you will arrive at The Hilltop restaurant. Amazing fried fish, chicken, beef Manhattans and other goodies. They have a salad bar with homemade salads, desserts and a homemade cheesespread. Be careful where you park because you might be parking where the horse & buggies park.
When you leave you will want to turn left and head west on US 20. Eventually (5 miles) you will hook up with the US 20 bypass and it will take you to I80 west of South Bend.
On your back return the same way (via US 20) and go past The Hilltop and 5 minutes east of Middlebury on US 20 you will come to the Rise and Roll Bakery. This place is almost indescriably good. They have lighter then air donuts that are nothing short of amazing. They serve Smoked Sausage Bread w/sausage gravy that is simply the best “biscuit & gravy” dish I have ever had and I have tried those literally all over. The cinnamon/caramel donut is a MUST! This is Amish cooking and baking at it’s very best.
When you leave turn back west go up the hill turn right go through Middlebury and you will again connect up with I80.
These suggestions may take you off your path a bit but I assure you it will be worth it.