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Thank you for contacting the Intel community.
Yes, the Intel® HD Graphics 5500 supports two monitors. The problem you have is that you are using an adapter from USB to VGA and this conversion will never work, please bear in mind that USB is only to pass information from one device to another but it does not output any video.
In order for you to get dual display with this computer you can connect a VGA cable from the Laptop to the monitor and get an HDMI cable to connect from the Laptop to a HDMI port on the monitor if the monitor has HDMI ports.
As well you can try a HDMI to VGA converter to connect the VGA monitor but I cannot guarantee performance or full functionality, you can check for an adapter at:
NOTE: This link is being offered for your convenience and should not be viewed as an endorsement by Intel of the content, products, or services offered there.