@Inna22 , some of mine recently want me to be both travel agent, recommending itineraries, and adventure outfitter, renting their canoes for them and helping with meal planning.
I'm helpful: I point to the guidebook for what to do and how to rent equipment. I point to google for camping recipes. I did make up a google map of canoe launch points along with estimated paddling times, but that link is saved for booked guests. That information really is something they would have trouble finding themselves. It isn't generally google-able.
Airbnb does encourage guests to ask for, and "compliment" the host on, local tips, so it's not so strange that guests take that a little further into travel agent territory. I agree that it is a fairly new phenomenon, though. Maybe it's in bigger font now...
So anyway, what do you recommend I see in Chicago? 😉