Chessie functions as a conversational guide, responding to queries about neighborhood culture, dining, and historic landmarks. The interface allows travelers to input specific needs—such as family-friendly constraints or multi-day scheduling—to receive tailored suggestions. According to Visit Baltimore President and CEO Kireem Swinton, the project aims to simplify discovery for the 28.7 million annual visitors who generated $4.3 billion for the city’s economy in 2025.

Matador Network CEO Ross Borden noted that travelers increasingly prioritize AI for trip planning, making such tools essential for modern tourism. Baltimore joins a growing list of destinations, including Greece and New York City, that utilize the GuideGeek engine to manage visitor inquiries. By centralizing information on sites like Fort McHenry, the National Aquarium, and the city’s 250 distinct neighborhoods, the platform seeks to convert digital engagement into on-the-ground exploration.