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Gradual typing has emerged as a promising typing discipline for reconciling static and dynamic typing, which have respective strengths and shortcomings. Thanks to its promises, gradual typing has gained tremendous momentum in both industry and academia. A main challenge in gradual typing is that, however, the performance of its programs can often be unpredictable, and adding or removing the type of a a single parameter may lead to wild performance swings. Many approaches have been proposed to optimize gradual typing performance, but little work has been done to aid the understanding of the performance landscape of gradual typing and navigating the migration process (which adds type annotations to make programs more static) to avert performance slowdowns. Motivated by this situation, this work develops a machine-learning-based approach to predict the performance of each possible way of adding type annotations to a program. On top of that, many supports for program migrations could be developed, such as finding the most performant neighbor of any given configuration. Our approach gauges runtime overheads of dynamic type checks inserted by gradual typing and uses that information to train a machine learning model, which is used to predict the running time of gradual programs. We have evaluated our approach on 12 Python benchmarks for both guarded and transient semantics. For guarded semantics, our evaluation results indicate that with only 40 training instances generated from each benchmark, the predicted times for all other instances differ on average by 4% from the measured times. For transient semantics, the time difference ratio is higher but the time difference is often within 0.1 seconds.