Can you get a reply from a HTTPS site using the Ping command?

The answer to your question (Can you get a reply from a HTTPS site using the Ping command?) is Yes, you can, as long as ICMP replies are enabled on the HTTPS site provider. However, it has nothing to do with HTTP or HTTPS:

Ping will use ICMP protocol, it belongs to TCP/IP Internet Layer, which is a lower layer than HTTP or HTTPs (from Application Layer):

Ping operates by sending Internet Control Message Protocol (ICMP) echo request packets to the target host and waiting for an ICMP response. In the process it measures the time from transmission to reception (round-trip time)1 and records any packet loss. The results of the test are printed in form of a statistical summary of the response packets received, including the minimum, maximum, and the mean round-trip times, and sometimes the standard deviation of the mean.

You can test with "cmd" (Windows Start button / type cmd in the search box, open "cmd.exe"), then with ping:

ping www.hotmail.com

If you try to ping a HTTP URL, such it follows:

ping http://www.hotmail.com

You will get the same error that you would get when trying to ping a HTTPS based URL:

ping https://www.hotmail.com

(An error something like that ping cant reach the requested address will appear on both attempts).

ping works at a much lower level than HTTP or HTTPS, and only accepts hostnames, not URLs. For example:

ping www.google.com

tcping - simulate "ping" over tcp by establishing a connection to network hosts. tcping at application level will send SYN, waiting for ACK, closing with FIN ACK

C:\>tcping google.com 443

Probing 87.106.83.127:443/tcp - Port is open - time=19.787ms
Probing 87.106.83.127:443/tcp - Port is open - time=20.487ms
Probing 87.106.83.127:443/tcp - Port is open - time=24.494ms
Control-C

Ping statistics for 87.106.83.127:443
     3 probes sent.
     3 successful, 0 failed.
Approximate trip times in milli-seconds:
     Minimum = 19.787ms, Maximum = 24.494ms, Average = 21.589ms

You can issue a HEAD request with OpenSSL:

openssl s_client -quiet -connect github.com:443 <<eof
HEAD / HTTP/1.1
Connection: close
Host: github.com

eof

Note that you can also use "HTTP/2", but be careful because some servers (e.g. github.com) do not support it.