My experience -

Highly recommend scheduling a taxi. When you schedule on Uber/Lyft, it doesn’t really book it. It just puts a timer on your behalf and attempts to schedule it when it is time and that would depend on available riders.

Scheduling a taxi let’s you sleep peacefully confident that your ride is going to be there.

I've had no problems getting Lyfts and Ubers at 4am when leaving work in Fort Point/Seaport. General wait was 4-5 minutes with range from 1-10. It's a mix of drivers ending their night and ones beginning theirs.

Recommend scheduling a taxi.

I got lucky and ubered around 4AM one time for a 715 flight but honestly I wouldn’t take that chance again

I have taken Ubers to Logan around that time a couple of times recently and it has worked out fine.

I did it this morning for a 5am flight and Uber worked fine. I allowed an extra 15 minutes in case it took a while to find a driver but I didn't need it.

You can schedule an Uber in advance. I have done it for early morning runs and it has worked fine. You will get a message telling you who your driver is in advance.

It probably depends some on where you are starting from—is it an area where it's generally easy to get rides without a long wait? Are you in the heart of the city?

I fly two Mondays a month at ~7 AM, have never been remotely close to missing my flight with a 4:45 AM scheduled Uber + TSA Pre. I used to schedule a cab but the company I used upped the cost to $80 whereas Uber is typically 40-50 bucks. If you're worried, call a reliable cab company, but coming from Waltham and Watertown I've never had an issue with the scheduled Uber.

With that being said, I hate that Uber is so much cheaper because they just fuck over the drivers and I'd much rather pay a cab driver, but the pricing is just not competitive at all in my areas.

except when it's not.... I've had taxi's no-show multiple times; it's a crap-shoot.

Lyft has a schedule ahead option which I always use to schedule the night before for flights that early. I've never had am issue getting a driver that way.

I do it 1-2 times a month from Quincy with no issues. I've never had to wait more than ten minutes as early as 430.

I would suggest a taxi, as it's much more reliable. I use Cabbie's Cab and have never had a problem. In fact, they're always early even at 3:45am!

I’ve done this several times too and have never had an issue

It’s not a weekday, but I had no trouble getting a Lyft to Logan at 5am this morning. I’ve gotten one early on a weekday before too and it was fine.

I scheduled an Uber for a 5am flight in early Nov - worked out great, though the rate was higher than if I'd done the request that morning. FYI Logan TSA wasn't open when we arrived a few minutes after 3am

I've had taxis no show me and have dispatch be rude as fuck about it.

The taxi app Curb is great. It predates Uber and the prices are usually better than Uber.

I have had no problem scheduling an Uber to Logan for those early morning hours!

I’ve never had a problem at the hour. My fiancé just flew out 2 weeks ago and had no problem getting one at 4:15 AM.