Using AI Chatbots to Plan a Vacation –

This post may contain affiliate links and Corporette® may earn commissions for purchases made through links in this post. As an Amazon Associate, I earn from qualifying purchases.

My husband and I are going to Chicago for our wedding anniversary, and while he’s visited the city before, I’ve only passed through via O’Hare — so I’ve been playing around with using AI chatbots to plan a vacation. While it’s a good problem to have, travel planning on the internet can be overwhelming because there’s SO much to sift through: so many “best of” lists, so many customer reviews (which may or may not be reliable), and so on. I don’t have a ton of time or energy right now to do lots of Chicago research, so I thought I’d try getting AI to help, at least as a jumping-off point.

What are your favorite ways to research a travel destination? Do you ever use a travel agent? What are your favorite travel forums or websites? (And what are some great tips you’ve gotten from Corporette readers?)

Most of my experience with AI chatbots so far has been with my 12-year-old son, who’s really into computers and technology. We’ve experimented with OpenAI’s ChatGPT and Google’s Bard over the last couple of months, together and separately. (Looking at my ChatGPT history, he’s asked it things like “What was the most unethical experiment ever?” and “How is an AI aware that it is not truly sentient?”) One day recently, I randomly thought to ask about cat cafes in Chicago, and then I started asking more about the city.

Disclaimer: As a New York Times story explained earlier this week, not only do AI chatbots sometimes provide incorrect information, but they occasionally, uh, make things up. (The developers call this … “hallucinating.”) So for one, when you’re researching a vacation spot, you should double-check that any recommended restaurants and other businesses are still around.

Pros & Cons of Using AI Chatbots to Plan a Vacation

While playing around with AI travel planning, I’ve noticed some pros and cons:


  • No ads!
  • ChatGPT and Bard are free to use. (OpenAI’s ChatGPT Plus is $20/month.)
  • Having a text-only interface and zero filler can help keep you focused when you don’t have much time. And if you want to see what a certain hotel looks like, for example, it’s easy enough to just google it afterward.
  • You’ll save time! AI chatbots give you distilled, short-and-sweet answers. If you ask about a type of restaurant, for example (more on that later), ChatGPT typically gives you a list of five options. This is great if you don’t want to be overwhelmed by lots of Yelp reviews, travel websites/blogs, Reddit recs, etc., along with evaluating which “10 Best [Things] in [Place]” article is most trustworthy.


  • ChatGPT’s and Bard’s answers are far from 100% reliable, making it important to spot-check the info they provide.
  • You won’t know exactly where the chatbots are getting the info they present, aside from, you know, “the internet.”
  • ChatGPT admits it has “limited knowledge of world and events after 2021.” For example, it could potentially give you a rec for a restaurant that used to have a good reputation but crashed and burned, or that was closed by the health department — rats, anyone? — and reopened. Also, URLs might be out of date.
  • In general, AI can be biased.
  • This may be a big one for some people: As you can probably tell from the “pros” above, it’s just not as fun as other ways of researching a trip.

Let’s go straight to the horse’s chatbot’s mouth. Here are the advantages and disadvantages according to ChatGPT (a summary of a much longer answer it gave me initially):

Using ChatGPT to plan a vacation has advantages such as access to a vast amount of information, personalized recommendations, quick and convenient access, and availability 24/7. However, there are also disadvantages, including a lack of human touch and empathy, limited interaction, overreliance on technology, and a lack of context. It’s important to use ChatGPT in conjunction with other sources of information and advice, as planning a vacation involves more than just logistics and information.

{related: open thread: how to take the stress out of vacation planning}

My Tips for Using AI Chatbots to Plan a Vacation

I’m not an expert in planning a vacation with AI by any means, but in my experiences so far I’ve found some strategies.

From the start, I decided not to bother asking super basic questions like “What are the best hotels in Chicago?” or “What are the best pizza places in Chicago?” because they didn’t seem like the best use of AI. I got more specific and asked about “quirky places for shopping, “deep dish pizza restaurants popular with locals,” and “museums that don’t take too much time.” ChatGPT typically gave me five options, each with a one-sentence description (along with URLs when I asked).

Try words and phrases like “unusual,” “popular with locals,” “authentic,” “best-kept secret,” etc., instead of “best.” (Is that a guarantee that you’ll get what you want? YMMV.)

To save time in your planning, ask for “[type of cuisine] near [hotel]” and you’ll instantly get a short list of restaurant names/descriptions without even having to bother with a map. (I’m not great with maps, and having to keep zooming in and out on gets annoying.) As an example of the alternative, I googled “Chinese restaurants near the Chicago Athletic Association — where we’re staying — and was presented with 22,000,000 search results.

Remember that, ChatGPT isn’t up-to-date on a lot after 2021, so asking something like “What touring Broadway shows will be in Chicago in June 2023?” probably won’t get you anywhere. Researching annual festivals makes more sense.

Here’s something interesting: I asked about “quirky/different sort of hotels” in a Facebook group where my college’s alumnae/i share travel advice (another great way to research destinations!), and my husband and I chose one of the recommendations, the Chicago Athletic Association. After we booked it, I asked ChatGPT a similar question, and it was one of the chatbot’s five recs, too.

{related: have you ever taken a vacation alone?}

Where to Keep Your Research When Using AI to Plan a Vacation

Nothing ground-breaking here, but I created a Google doc to dump everything into and then shared it with my husband. We can fine-tune and spot-check and make decisions later. I’m very glad I did that, BECAUSE for some reason, none of my Chicago-related Q&As got saved in my account, which I only just discovered. Thanks, ChatGPT.

In general, though, all of your Q&A exchanges are saved in your account, and you can rename them to make them more easily identifiable, or simply delete them.

Do tell, readers: Have you used or would you consider using AI to plan a vacation? (Also, tell us about your summer destinations this year!) Have you used AI chatbots for anything else yet, including work?

July 2023 Update

We had such a great trip! The ChatGPT suggestions we used — and loved — were the Architecture River Cruise (granted, we would have done that anyway), Goddess and the Baker (loved this cafe, where I discovered that cruffins are a thing, YUM), MingHin Cuisine (excellent dim sum), Lou Malnati’s (amazing deep dish and garlic bread), and the Chicago Athletic Association (a unique, splurge-y hotel). Our lucky Yelp finds while were there were Amorino (loved my tiramisu gelato) and Pinched on the River (best falafel ever), and while I can’t remember exactly how my husband found out about Eggy’s Diner, we had a delicious brunch there (strawberry, banana, and Nutella crepe, yes please!).

Random opinions: I found The Navy Pier weekday fireworks underwhelming, and I recommend visiting Lurie Garden while you’re exploring Millennium Park. Next time I’d like to check out Second City, the International Museum of Surgical Science, the American Writers Museum, The Catcade, and the Garden of the Phoenix (in cherry blossom season!).