Coming into Chicago for 3 days last week of October. Hubs and I not sure whether to book architectural river tour now or wait until we get there depending on weather. Should we wait or take a chance?
Wait until you get here to see what the weather is like. It's unlikely tours will be fully booked, especially if you have some flexibility on when you can take it.
Last week in Oct could be very cold & damp with rain. So yes wait till you are here.