A method includes determining a travel itinerary that includes a first segment that is scheduled to arrive at a location at an arrival time and a second segment that is scheduled to depart from the location at a departure time. The method also includes deriving a probability distribution of delays in the arrival time based on an arrival statistical model of the first segment, retrieving a minimum connection time required by a traveler traveling in the first segment to connect to the second segment, and computing a likelihood that the traveler will fail to connect to the second segment based on the probability distribution of delays in the arrival time. Annotations are derived from the computed likelihood and added to the travel itinerary.