Tues: so far our plan for the day of our check in isn't planned since we'll probably be tired. (Check in at 3pm, thought about maybe a Broadway show at 8pm but we have to be up at 6am the next morning so not sure what to do that evening)
Weds we're going to do Moving Image Museum, FAO, Brooklyn Bridge (hotel is in Brooklyn). (We have previous engagements Weds morning from 6am-1pm so it's a half day)
Thurs: SOL, Ellis Island, Paul's Chapel and walking to Chelsea Market. (Yes I realize this is a "long" walk) We'll stop in shops on the way, take photos, and really want to take in the city.
Friday: NY Transit Museum in Brooklyn (opens at 10am), Train to Hell's Kitchen (eat lunch there), Times Square, Walk from Columbus Circle the mile or so through the park to arrive at Central Park/59th, Walk to St Thomas, Berlin Wall (520 Madison), St. Patricks, and then Grand Central Terminal for the audio tour. Again thought about maybe doing a Broadway show perhaps this evening, the show we want though is 2 hours or so long and only is on at 8pm so by the time we'd be back to the hotel it'd be closer to 11pm with a long drive ahead of us the next day.
Saturday: Check out is 12pm and we have a 11-13 hour drive back to Chicago should we try to squeeze something else in and leave right at 12pm or leave early say 7-9am? If your opinion is to try to squeeze one more thing in-what? I've thought we can be safe and just walk around Prospect Park, Park Slope, see the Brownstones, etc or thought maybe we can take an early subway around 7am to Greenwich Village (approx 30-40 minute subway ride) so if we arrived at 8am and left around 10:30 we should be back with plenty of time to check out if we pack the night before. Any opinions or ideas of what to do in such a short time frame?