Wireless SWD interface
There won't be an easy solution to your problem except for the obvious things like using a wireless USB hub (even these don't work too well for some things, I tried running a sensor suite for real time data collection and wireless usb has some failings and connection problems).

The SWD would be difficult to transmit over wireless, since it's a two wire bus and bi-directional, this means that a wireless "bridge" would have to have some micro controllers that could talk to each other at a much higher rate than the SWD bus. Wireless modules are available for SPI, but not for I2C. 

The easiest thing to do would be to run a raspberri pi or some other computer with GDB or this module that uses a GDB server with wifi.