This article analyzes possibilities for connecting individual city games for building a network of games working together. City gaming works along with the understanding that cities are self-organizing systems, influenced by multiple bottom-up and top-down actors with varying interests and powers. Affordable housing, climate adaptation, or area development are examples of urgent urban challenges city games typically focus on. The assumption is that if these specialized games could be linked, then a large game infrastructure built as a modular system, can offer various game combinations responding to urban challenges in an integral and holistic way. To test a working game network, city games, models, and digital apps have been linked through their shared datasets as well as game interfaces. Two city experiments have been conducted in two Dutch cities—Amsterdam and Breda—which enabled the testing to function as “constructive design research.” In Amsterdam (Klimaatspel) two separate city games were connected through their datasets, while in Breda (Play the Koepel) datasets and interfaces merged to create a new game. Used data models are the Energy Transition Model developed by Quintel and the urban plan cost simulator software of Urban Reality. Used game interfaces (digital and analog) include the Typeform, the Network of Games app, the Urban Reality simulator, and the Play the City table-top game format. The testing considered two different approaches for a potential game network. The first option assumes an all-encompassing digital app, reformatting and involving various games and models in a single interface. The second option is an open approach that looks to link custom-made games with existing interfaces. The second option allows both simultaneous and sequential linking. Two experiments utilizing sequential and simultaneous integration of diverse digital tools suggest that a collection of interfaces connecting to each other throughout the entire process from a digital poll to an app, a simulator or a webinar, or analog game sessions is more effective than a single mobile phone app for all potential game interactions. Considering city games as an ecology of city tools that can be linked to one another becomes through this study a concrete goal to reach. Through combining specialized games, addressing complex city challenges becomes possible. This step enables a more effective participation environment for diverse experts and non-experts.