I travel via taxi often for work, and getting to the Boston airport is a burden at times, especially early (4am or 5am) in the morning. Luckily I have a few options for the airport, such as the subway or a taxi.
My current favorite though, is UberX from Uber — in particular, the ride is around $25 to the airport (a bargain, in my opinion). And the best part is there’s no calling involved (who uses the phone anymore?) — I tap my location and request a driver in a couple of steps on my phone (android for me, but iOS devices work well too).
Some caveats — with UberX many times the drivers are new, and need some guidance for directions since they’re in a new neighborhood (or ask them to plug it in their GPS). So some direction is needed to help the driver out. Uber Black is much higher quality (all are limo drivers), although much more expensive — around 2x more in my experience (and out of my budget).
Also, to help with a cheaper first ride, here’s an uber promo/coupon code for free $20 when signing up with Uber (promo code: uberfree20ride ). Check it out!