Flights: predictability. Almost always that means the optimal route on an airline where I have some status to help in the event of IRROPS.

Hotels: I like some variety, although the degree varies by city and trip. On some trips, my "variety" may simply be a different chain hotel. (Ooooh...a Marriott this time instead of a Sheraton. Exciting! ) Other times it's skipping the chains entirely to stay in a B&B, apartment, pensione, or other boutique hotel.

Food: almost always variety and local restaurants. Equally true if it's Tulsa or Paris. If I frequent a city often, I may find the local restaurants I like and go back, but I'm always looking for something new. If I venture into a chain of any kind, it's perhaps for a quick lunch during a business trip (e.g., a Chipotle if we're just going back to a meeting room to keep working). Or perhaps the afternoon Starbucks run...