Planning the next road trip...

We just got back from WDW by way of a road trip from Upstate NY here. Loved Disney of course as well as loved even more being on the road.

Now we're looking into our next one that will take us from here (Upstate) to Navy Pier in Chicago then onto Washington DC then to NJ, for the sake of wanting to actually go to NYC but not wanting to drive in NYC. We've been to Ocean City, NJ before and absolutely loved it there. So may choose to go there, unless we can find an area that is closer to New York, where we can take a train or so back and forth.

So looking for ideas from any who may have visited these areas as far as nearby hotels and interesting stops along the way. We would need enough room(s) for 3 adults and a child. Myself, my boyfriend (not sure if anyone actually spells that out anymore...lol), my younger sister and her daughter. So may look into 2 rooms depending on prices.

TIA