You can absolutely do either — but choosing to book in advance is the better move whenever the trip matters. Advance booking locks in your vehicle, your price, and a driver who has your itinerary before the day starts. Last-minute booking works when fleets have slack, which means weekday middays, not Friday nights, holiday weekends, or prom season. The rule is simple: the more the trip matters, the earlier you book.

Here is how to think about timing for each kind of trip.
Book early: airports, events, weekends
Airport pickups deserve advance booking every time. Your driver needs your flight number to track delays, your terminal to plan the pickup, and your party size to send the right vehicle — none of that happens well in a 10-minute scramble. Same logic applies to weddings, proms, and any Friday or Saturday night: demand peaks, the best vehicles go first, and booking a round trip in advance is cheaper than solving each leg under pressure.
How early? For a standard airport transfer, book in advance by 24 to 48 hours. For weekends, book in advance by a week. For prom season, weddings, and December holidays, think in months — the companies will tell you honestly if you are early, and early is never a problem.
Last-minute: when it actually works
Last-minute booking shines for simple trips at off-peak hours: a Tuesday afternoon ride across town, a backup plan when your first option falls through. Most companies keep cars moving all day and can often cover a request with an hour or two of notice — last-minute limo requests get filled more often than people expect.
What you give up is choice and certainty. The vehicle you want might be out, the price might carry a short-notice premium, and during peak times the answer might simply be no. If you must book last-minute, call instead of booking online — a dispatcher can tell you in 30 seconds what is actually available.
What to have ready when you book
Whether you book a month out or an hour out, have the same details ready: pickup address and time, destination, passenger count, luggage count, flight numbers for airport trips, and a contact number that will be on during the ride. Companies that take online reservations will ask for all of this in the form — having it ready makes the booking take two minutes instead of twenty.
For airport pickups, share your flight number even if you think the flight is on time. Flight tracking is how good companies adjust for delays without a phone tag, and it costs you nothing to provide.
The honest trade-off
Choosing to book in advance buys certainty: the right vehicle, a confirmed price, and a driver who has seen your itinerary. Last-minute booking buys flexibility at the price of uncertainty. Neither is wrong — they are just different products.
My advice: if the trip has a hard deadline — a flight, a wedding, a show — book in advance and stop thinking about it. If it is a casual crosstown ride on a quiet afternoon, book whenever. And whatever you do, use a TLC-licensed company — licensed operators are the ones with real dispatch systems that honor advance reservations. If you are visiting, NYC Tourism points visitors to licensed ground transport for the same reason.