CMOS technology scaling has enabled dramatic improvement for digital circuits both in terms of speed and power efficiency. However, most traditional analog-to-digital converter (ADC) architectures are challenged by ever-decreasing supply voltage. The improvement in time resolution enabled by increased digital speeds drives design towards time-domain architectures such as voltage-controlled-oscillator (VCO) based ADCs. The main challenge in VCO-based ADC design is mitigating the nonlinearity of VCO Voltage-to-frequency (V-to-f) characteristics. Achieving signal-to-noise ratio (SNR) performance better than 40dB requires some form of calibration, which can be realized by analog or digital techniques, or some combination. This dissertation proposes a highly digital, reconfigurable VCO-based ADC with lookup-table (LUT) based background calibration based on "split ADC" architecture. Each of the two split channels, ADC "A" and "B", contains two VCOs in a differential configuration. This helps alleviate even-order distortions as well as increase the dynamic range. A digital controller on chip can reconfigure the ADCs' sampling rates and resolutions to adapt to various application scenarios. Different types of input signals can be used to train the ADC’s LUT parameters through the simple, anti-aliasing continuous-time input to achieve target resolution. The chip is fabricated in a 180 nm CMOS process, and the active area of analog and digital circuits is 0.09 and 0.16mm^2, respectively. Power consumption of the core ADC function is 25 mW. Measured results for this prototype design with 12-b resolution show ENOB improves from uncorrected 5-b to 11.5-b with calibration time within 200 ms (780K conversions at 5 MSps sample rate).