Vrbo listing optimization is the work I do to make a property rank, convert and price correctly on Vrbo. I rewrite your headline and description for Vrbo's family and group guests, order photos to sell the whole home and tune rules and settings.
What I plan around in Chicago: Lollapalooza and summer festivals; McCormick Place conventions; Cubs, Bears and Bulls seasons; Christmas markets and Magnificent Mile lights. Guests I price for: Weekend leisure guests, convention attendees and families visiting Wrigleyville, River North and the West Loop. Where I start: Summer-heavy seasonal spread, convention and concert premiums, and winter floor pricing paired with longer minimum stays.
Chicago sells mostly through Airbnb, Vrbo and Booking.com. I set up your Airbnb, Vrbo and Booking.com strategy with you so festivals, conventions, sports and holiday weekends each have their own rate and minimum stay, with weekly and monthly rules that keep winter calendars from going empty between January and March.
The service in general is described on my vrbo listing optimization page; this page covers how I apply it in Chicago.