Is it possible to connect and run two portable external displays from Macbook Pro or Air?

Yes, it is possible to connect and run two portable external displays from both MacBook Pro and MacBook Air models, but the specific capabilities depend on the MacBook's chip, Intel chip based or Apple Silicon one and the connection methods used. Modern MacBook Pros and some MacBook Airs with the M3 chip or later can natively support two external displays when the laptop lid is closed. Other models may require workarounds like using a DisplayLink Adapter or self powered Hub. 

Check the tech specs for the model of interest. Lower-spec Apple silicon processors can usually support two displays, one of which can be (or is) the internal display for a laptop.

Higher-spec Apple silicon (Pro, Max, Ultra) can support more than two displays, though the allowed limit varies.

As for whether a particular monitor can draw (any, or enough) power from the connection, check the monitor specs. That’ll tell you which connections are required, and how much power.

Probably the easiest approach involves bringing the monitor and its cable to an Apple Store if there’s one nearby, and testing it.

• M-Series MacBook Pro with the M-series Pro chip is good for 2 external monitors, The Max CPU chip is good for up to 4 depending on pixel densities, as well as the laptop display.

• The M1 and M2 MacBook Air is good for a single external display
• The M3 MacBook Air can drive 2 external displays BUT you have to close the laptop lid and use it in clamshell mode.
• The M4 MacBook Air can drive 2 external displays AND the laptop display.

Other options are the use of DisplayLink adapters and DisplayLink software to add more monitors than the Mac can drive with the native GPU.

https://www.synaptics.com/products/displaylink-graphics/downloads/macos