An Airbnb pricing strategy is the set of rules that decide what each night is worth: base, minimum and maximum prices, seasons, events, minimum stays, gap nights, last-minute pricing, length-of-stay discounts and channel markups. The tool applies the rules; the strategy is what makes the tool worth having. Smart Pricing is not a strategy, because it optimizes for Airbnb's fill rate and knows nothing about your events or other channels.
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.
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 airbnb pricing strategy page; this page covers how I apply it in Chicago.