To provide students at our own institution with more accurate and granular data regarding the costs associated with applying for residency. We created an electronic survey with >28 different fields delineating the costs associated with applying for residency. Demographic data, costs broken down by type of expenditure, and how these costs were financed were measured. Each year, graduating students at our institution took the survey in 2015, 2016, 2017, and 2018 before The Match. We then created a dynamic, user-friendly, and interactive Web-based application to display these data numerically and graphically for students to use while planning and preparing for The Match. There was a response rate of 48.9% (194/397). Overall, students completed an away rotation at a median of 1.0 (interquartile range [IQR] 0-2.0) programs and spent $1000 (IQR $292-$1606) per away rotation. They applied to a median of 30.0 (IQR 20.0-47.8) categorical programs and attended 12.0 (IQR 10.0-16.0) interviews. The cost per interview was $282 (IQR $192-$407). The total expenditures for preparing for residency were $4992 (IQR $3034-$8,274). These numbers varied significantly by intended specialty. Differences were noted between our data and those from both a regional and recent national cohort. The costs associated with applying for residency are relatively unknown and can be significant for some. Institutionally led efforts may allow students to more appropriately plan and budget for The Match. Other institutions may benefit from a similar program.