Chatflights can help you book better award tickets — here's how

Award booking services aren't a new phenomenon. Over the years, we've seen these services come and go, and I've even worked for a couple of them. In short, these services take a travel agent-like approach to the process of redeeming points and miles. You tell them your dates, destinations and mileage balances, and they'll find award space — and book the tickets for you. Oftentimes they'll work to find the best possible deal for you as well.

This takes a lot of the heavy-lifting out of the award booking process. All you need to do is focus on earning points, and then you can offload the research and booking to an expert.

That said, these services don't come cheap — many times, you'll pay hundreds of dollars for a round-trip booking on top of the taxes and fees associated with your ticket. Plus, it can take some time to find an award booking service that works for you, as each has its own specialties and forms of communication.

One of the most interesting award booking services is Chatflights. This service takes a mobile-only approach where all correspondence between you and your booking agent is through instant messages on the Chatflights app. This lets you skip email correspondence and have a real-time conversation about your tickets, something important when you consider how award space can change on a dime.

Let's take a closer look at Chatflights and whether or not you should utilize this service.

using Chatflights to book an award ticket

Chatflights aims to take you from start to finish on any award trip. You open a request in the Chatflights app and give the system your trip details and points balances. Then, you're connected with an agent who will look for flights for you. After some back-and-forth conversation to zero in on the best award option, the service will then book the flight and invoice you.

In a discussion with Chatflight's founder, Malte Barnekow, I was told that all searches are performed manually, and there are no chatbots or other automated assistance involved in the process. He told me this was to provide the most personal experience possible, which I found to be true with my own Chatflights booking experience.

Barnekow also told me that the service focuses almost exclusively on first- and business-class tickets. That said, you can request an economy ticket if you'd like. The service also offers round-the-world bookings for an additional fee. These tickets can take a lot of effort to book, so Chatflights can be a great option for maximizing your points on these types of redemptions.

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Related: What are the differences between business class and first class?

The service is only available as a mobile app at this time, so all communication is handled through instant messages. This is actually a good thing for award bookings, as award space can disappear in an instant. Most other award booking services handle all communication over email, which can take longer and may lead to lost award tickets.

That said, Barnekow ensured me that members can request a phone call if needed.

So ... what's the Chatflights experience actually like? Here's a look at my experience booking with them.

My experience using Chatflights

I'm in the midst of booking a trip from New York to Ukraine, as the country recently started admitting American tourists. In an effort to test the service, I downloaded Chatflights, created an account and opened a new booking from the home screen

The first couple of screens were pretty straightforward: I inputted where I was traveling to and selected whether I needed help with booking a hotel, rental car or an airport transfer.

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(Screenshot courtesy of Chartflights)

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With that out of the way, I was brought to the points balances screen. Here, I had to manually enter balances for all of my current rewards currencies. I ran into a snag when attempting to add my American Express Membership Rewards balance to the app, so I reached out to the Chatflights team, who confirmed they do work with Amex points. So, I simply added another line for American Airlines miles and left a note saying it was actually for Amex points.

I was then asked for my departure airport and dates of travel. The app asks for your earliest date of arrival and latest date of departure so that the agent can search in a range. There was also a text box that asked me for any other notes I'd like the team to know.

Then, I submitted my request.

Amazingly enough, I heard back from the booking agent within minutes. I was surprised to see such a quick turnaround time given I submitted the request around 5:30 p.m. Eastern Time. The agent asked if I was all right with a longer flight for a better in-flight experience. I told the agent I was and then logged off the app for a couple of hours.

The agent sent me itinerary options later that evening, coming up with an outbound departure on KLM and return flight on Qatar Airways. We reviewed the request together, and I picked the flight options I liked the most. The KLM option was 53,000 Amex points transferred to Flying Blue — a great value for KLM business class. The Qatar flight was 90,000 Amex points transferred to Asia Miles. Both are good options — especially considering the return flight was in Qsuite business class.

It's worth noting that the return flight had an overnight layover in Doha (DOH). The agent informed me that this was due to award space and that a flight to Chicago-O'Hare (ORD) was available with a shorter layover. I could then book a separate ticket to New York to get home. This was a thoughtful touch and it was nice to see the agent looking at all available options before sending me the flight details.

After I confirmed the flights, I was told where to transfer my Membership Rewards points. The agent informed me that Chatflights can create these loyalty program accounts for me if I didn't already have them set up. After doing this, my flights would be booked and I'd be invoiced for the cost of the award ticket's taxes and fees plus the $350 booking fee. I'll discuss this fee in the next section.

Overall, the process took two days, but this was mostly due to me confirming flights with a friend who was also traveling. I found the service to be quick and efficient, and I have no doubt that it could be completed faster. All flight information was forwarded to me in the app as well for quick reference at the airport.

My only gripe with the experience was the initial setup process, as it felt a little bit clunky and unnatural at times. For example, it was strange that the app didn't recognize Membership Rewards — one of the most valuable currencies out there. Likewise, the process of adding my destination and dates of travel was a bit confusing. I would like to see an enhanced design for these steps that makes it feel more like a traditional booking experience.

Chatflights pricing — is it worth it?

Of course, using Chatflights isn't free, and the service isn't for everyone. Here's a look at the pricing and whether or not it's worth it for you.

Chatflights pricing structure

Chatflights charges per booking, per passenger — here's a look at pricing:

• $350 per person: business class (or lower)
• $450 per person: first class
• $850 per person: round-the-world

There's no doubt that these are high fees, but you only have to pay once your flight is booked. This means there's little risk in using the service, since you only have to pay once your itinerary is confirmed. If you're not satisfied with the options, just close out the request and you've lost nothing.

Note as well that support from Chatflights doesn't end once your flight is ticketed and confirmed. The service can also help you with flight changes and cancellations. This can be a huge help when booking travel during the coronavirus pandemic, as airline hold times are still longer than usual. This is also important when working with smaller transfer partners like Avianca LifeMiles who have notoriously-difficult support lines. This alone can be an easy way to justify the cost of using Chatflights.

Who should use Chatflights?

Chatflights is best for those who aren't well-versed in award travel redemptions or simply don't want to spend time booking their own tickets. The service essentially lets you rent someone else's in-depth points and miles knowledge. Plus, it provides a curated experience that handles the award booking process from start to finish. This saves time and takes the most frustrating part of the award booking process — finding award space — out of the picture.

That said, points and miles experts with the time to book their own tickets may want to skip the service and book on their own. Likewise, if you think the $350 price per booking is too high, it's in your best interest to learn the tricks of the trade and book your own tickets.

Related: TPG beginner’s guide: Everything you need to know about points, miles, airlines and credit cards

Bottom line

For the right traveler, Chatflights can be a good way to find and book award flights, especially for lesser-known rewards currencies. It takes much of the work out of booking award tickets — all you have to do is text a booking agent your travel itinerary and points balances through the Chatflights app. This format ensures timely communication, which is important when booking hard-to-find award space.

So if you can justify the $350+ price tag, Chatflights can be a solid pick for your next award booking.