(Self-answering)
Assuming that Desmos is reliable, I now think that the product in the OP is approximately $0.99992076\times\dfrac{\pi}{2}$, so the conjecture is false.
Why I think the conjecture is false
Letting $f(n)=\color{red}{\dfrac{2}{\pi}}\prod\limits_{k=1}^n\left(1+\int_{k}^{k+1}\left(\frac{\sin (\pi x)}{x}\right)^2\mathrm dx\right)$, I found that:
$\dfrac{f\left(10^N\right)}{f\left(10^{N-1}\right)}\approx 1+4.5\times10^{-N}$ for $N=3,4,5,6,7,8$
$f(10^8)\approx 0.999920757989$ (found on Desmos; it may take a while to load)
This suggests that $\lim\limits_{n\to\infty}f(n)\approx 0.99992076$, so the product in the OP is approximately $0.99992076\times\dfrac{\pi}{2}$.
Given that, as the OP notes, $\int_0^\infty \frac{\sin x}{x} \mathrm dx=\dfrac{\pi}{2}$ and $\int_0^\infty\left(\frac{\sin x}{x}\right)^2\mathrm dx=\dfrac{\pi}{2}$, it is indeed a curious coincidence that the product in the OP is so close to $\dfrac{\pi}{2}$.
I still wonder if the the product in the OP has a closed form expression.
Most small numbers are near to simple expressions with $\pi$ or $e$
Pick a small random real number, say between $1$ and $2$. Round it to say four decimal places, and type it into Wolfram. It is likely that Wolfram will suggest a simple closed form involving $\pi$ or $e$. For example, I tried $1.2345$, and Wolfram suggested $\log (2e-2)$. We find that $\dfrac{1.2345}{\log (2e-2)}\approx 1.00002$.
Other curious findings about $p(x)=\frac{\sin (\pi x)}{x}$
- $\prod\limits_{k=1}^{\color{red}{10000}}\left(1+2\int_{k}^{k+1}p(x)^2\mathrm dx\right)\approx0.99992\left(1+\frac{e}{2}\right)$ but $\prod\limits_{k=1}^{\color{red}{100000}}\left(1+2\int_{k}^{k+1}p(x)^2\mathrm dx\right)\approx1.000005\left(1+\frac{e}{2}\right)$
- $\prod\limits_{k=1}^{\color{red}{100000}}\left(1+\frac{\pi}{2}\int_k^{k+1}\frac{|p(x)|}{x}\mathrm dx\right)\approx0.9999995\left(\frac{\sqrt{e}}{\ln 2}\right)$, but $\prod\limits_{k=1}^{\color{red}{1000000}}\left(1+\frac{\pi}{2}\int_k^{k+1}\frac{|p(x)|}{x}\mathrm dx\right)\approx1.00001\left(\frac{\sqrt{e}}{\ln 2}\right)$
- We have $\int_0^\infty p(x)^2\mathrm dx=\frac{\pi^2}{2}$, and the product of the arc lengths between neighboring positive roots of $p(x)$ is $\prod\limits_{k=1}^\infty \int_k^{k+1}\sqrt{1+(p'(x))^2}\mathrm dx\approx 0.9985\left(\frac{\pi^2}{2}\right)$.
Mathematical imposters
The OP is not the first time I've found a "mathematical imposter". Here is another one.