Parking behavior depends on drivers’ choice of parking type and willingness to pay for parking. Generally, the parking type refers to off-street and on-street parking facilities. The main factors affecting the preference for parking types are driver, vehicle, travel, and parking characteristics. Understanding drivers’ parking type preference behavior and accurately modeling drivers’ tendencies helps develop sustainable parking management policies. This study examines the parking preferences of drivers in Istanbul with binary logit models according to whether they pay for parking. The results of the models show that the number of factors influencing parking type preference is higher for free parking than for paid parking, including driver, vehicle, travel, and parking characteristics. Moreover, some factors in the models affect drivers’ parking type preferences differently for paid and free parking. Namely, low-income individuals tend to use on-street parking when parking is free and off-street parking when it is paid. Conversely, individuals who drive small-size vehicles prefer off-street parking for free parking and on-street parking for paid parking. Individuals who prefer off-street parking for free parking expect shorter walking distances to the final destination and parking duration. On the contrary, individuals who choose on-street parking for paid parking anticipate shorter walking distances to the final destination and parking duration.