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Why do Android users always miss out? This was my first thought when I tried downloading the Expedia app in order to test out its recently launched ChatGPT function, touted as using artificial intelligence to provide travelers with “recommendations on places to go, where to stay, how to get around, and what to see.”
Then I saw those frustrating words: Now for iOS with Android to follow
I looked at my Google Pixel phone as though it had failed me. How dare you not be an iPhone, I internally whined, knowing full well that I have always chosen the least popular, least compatible smartphones.
Officially released in April, Expedia adds to a number of industries adopting ChatGPT, sending many workers into existential crises over whether or not the technology will eventually replace them. To be fair, though, Expedia has always worked toward making travel agents obsolete with its one-stop-shop, DIY approach to planning trips, letting users search and compare everything from plane tickets to hotels and rental cars.
What, then, could Expedia gain from this “new in-app travel planning experience?”
As the company’s vice chairman and CEO, Peter Kern, says in a press release, “By integrating ChatGPT into the Expedia app and combining it with our other AI-based shopping capabilities, like hotel comparison, price tracking for flights and trip collaboration tools, we can now offer travelers an even more intuitive way to build their perfect trip.”
The perfect trip, you say? Does that apply to a place like Pittsburgh? I wondered what this shiny, innovative new toy was telling visitors about the City of Bridges — what landmarks to see, what hotels to stay in, what restaurants to patronize. Would it suggest the generic tourist route, with prompts to ride The Incline or shop for bootleg sports merch in the Strip District? Or would it think like a local?
App-wise, I would never know. Then I saw that Expedia also added a plugin that would allow the Android class to also participate.
Psych! The plugins have a waitlist, as ChatGPT is “gradually rolling out” this feature for Expedia and other entities.
Now to be outdone, I asked my husband if I could borrow his iPhone SE.
The ChatGPT function is front and center once you download the iOS Expedia app. Clicking on it, I was met with a message bubble reading “Hi. I’m an experimental travel assistant,” along with a prompt that gives some idea of how the technology works.
I typed that I was planning a trip to Pittsburgh. Immediately, ChatGPT responded with a message suggesting I go to the Carnegie Museums, the Duquesne Incline, and the Strip District. I chortled.
Getting started on Expedia’s ChatGPT function presents some degree of intimidation. After all, as Expedia points out, the tool can “deliver personalized and relevant trip options out of 1.26 quadrillion variables like hotel location, room type, date ranges, price points, and much more.” In other words, you have to be pretty specific in order to make it worthwhile.
So I made it personal, asking about aspects that I would realistically look for in any city. As a dog owner, I asked about pet-friendly hotels, and it spat back four options — the Kimpton Hotel Monaco, the Drury Plaza Hotel, the Fairmount, and the Sheraton in Station Square — along with information about additional fees and other criteria. Users were also cautioned to “check with the hotel directly for any specific pet policies or restrictions,” because ChatGPT covers its ass.
A question about vegetarian and vegan restaurants demonstrated the limitations of the service. Along with Apteka and Zenith, ChatGPT also recommended Onion Maiden and B52, two restaurants that closed. A question about vegetarian and vegan breakfast spots generated similar responses, along with Gluten Free Goat Bakery.
The most surprising response came when I asked about dance clubs. It recommended Belvedere’s Ultra-Dive for its “retro vibe” and eclectic mix of music, though out-of-towners looking for a more traditional club experience would probably be taken aback when they arrive somewhere that’s less bottle service and more PBR punk — something not expressed in the description. The South Side venue Scenario would present the most accessible option if not for it being, as a quick Google search reveals, “temporarily closed.”
I was also perplexed by the inclusion of Tilden and Hot Mass, as both cater to diehard, up-until-dawn DJ fans and, in terms of the latter, the LGBTQ crowd. The results made me wonder how many people are using Expedia’s ChatGPT to find something more specific than just dancing, as Hot Mass has often been viewed as a gay hotspot.
When asked about free activities to do during a specific weekend — in this case, July 7-9 — ChatGPT performed fairly well. It pointed out free tours at the Allegheny Observatory and a scenic stroll or bike ride along the Three Rivers Heritage Trail (the Strip District also popped up again, but I’ll let it slide.) It also boosted the Frick Art Museum, something I often recommend to people due to its (mostly) free admission and impressive exhibitions.
There were, like with the previous questions, some inaccuracies, as ChatGPT recommended free admission hours at the Phipps Conservatory and Botanical Gardens between 9:30-11 a.m. on Sunday. Not only did it flub the date (it said “Sunday, July 7th” instead of July 9th), but a representative confirmed for Pittsburgh City Paper that Phipps does not offer free admission to the public during those times.
Overall, ChatGPT still has a lot to learn about Pittsburgh, and, hopefully, as time goes on, will provide a more knowledgeable experience. For now, though, unless you want to Uber to a closed restaurant, you’re better off asking a local, or (heads up for shameless self-promotion) checking the Pittsburgh alt-weekly.
This article appears in Jun 28 – Jul 4, 2023.



