So how much time do we need off WORK?

Keep in mind we have several weekend days that take up our trip... So we won't need to take off 16 days. But it might be good practice for us to pretend we do, just so we have more than enough time saved up, since we might need to use up time for unexpected reasons before the trip.

There are a total of four weekend days during out trip... So we need exactly 12 days we can take off of work. This is also assuming we all take the 3rd of November off to rest.

How many days are we paying for out stay at the Motel 6 in Chicago...? 1 day.

How many days of that are we paying for The New Otani...? 12 days.