Travel enthusiasts relish in the jolt of excitement that comes from planning a trip. While some journey to known destinations others take vacations that require a bit more strategy and focus. Regardless of the type of travel, it’s important to build ‘wander time’ into the itinerary as a way to take in the surroundings without structure or time constraints.
Now, back to scheduling. Picture this: you’ve got your list of key places to checkout based on personal preference and recommendations from friends/other research but there are holes in the itinerary. Those holes could be filled with wander moments or you could build in even more points of interest.
Enter: ChatGPT. On a recent trip to France, CEO and Founder of The Neighborhood Hotel, Jonathan Gordon, had full days planned around Paris with his family.
“Before we left for Paris, I dropped all of our recommendations from family and friends into ChatGPT, along with our favorite spots, confirmed reservations, and hotel info. With this info, ChatGPT pulled everything together into a user-friendly itinerary. ChatGPT also suggested ways to fill in gaps in our schedule based on location and travel time—turning our plans into a smooth, memorable experience for the whole family,” Gordon says.
Gordon’s experience with ChatGPT’s assistance proved to be helpful, however, it’s not always such a seamless process [turns out robot’s aren’t perfect].
Forbes recently published an article with some helpful information and prompts to use when enlisting the help of ChatGPT for travel related planning. The following are some key takeaways from the Forbes piece.
-Daniel Levine, a keynote speaker specializing in tourism trends, is among the many travelers who have been experimenting with ChatGPT for travel planning. In his experience, he says, generative AI tools tend to do best when it comes to information that’s fairly static, like sightseeing: He recently asked an AI chatbot to plan a seven-day itinerary for a drive down the coast of Chile, and it produced a good starting point for an itinerary. On another trip, AI also revealed a little-known Terminal Transfer Bus that saved him time at Chicago’s O’Hare Airport.
These are 5 customizable ChatGPT prompts to help plan your next trip, complete with some parameters to help yield the most helpful results:
1. Recommend a [X-point] walking tour of [X city or neighborhood] within an [x-mile radius]
You can tweak this prompt so that it builds out an itinerary around a spot you’re planning to visit first.
2. Make a list of [X] expressions to help navigate [x country]
Use this as a cheat sheet to learn basic expressions in a foreign language.
3. Provide a list of the best [x type of cuisine] in [x city]
Be sure to fact check ChatGPT to verify all of the restaurants are still in business. You can also give it parameters such as “within walking distance of [x destination]
4. What are the top cultural institutions to visit in [x city]
For more niche responses, you can ask about historic cultural institutions, art institutions, etc.
5. Make a table of day hikes in [X destination} and include mileage, elevation change, and time needed.
ChatGPT can also produce tables and you can input information points you want included such as difficulty of the hike, average time it takes to complete it and more. This prompt works great for national parks.
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We experimented with ChatGPT just to see how accurate the results would be and to be honest, they were pretty spot on.
Search Phrase
“I am staying at The Neighborhood Hotel in Lincoln Park for our daughter’s graduation at DePaul University. We have Dinner at Ricardo Enoteca one night and I want to eat lunch at Parsons Chicago. I also want to go to the zoo and have a run on the lake. Can you help with travel recomendations to round out our weekend stay? Should we rent a car?”
Results
Absolutely! Here’s your weekend itinerary with approximate travel distances and times from The Neighborhood Hotel Lincoln Park (located at 2617 N Clark St, Chicago):
Transportation Overview
No need to rent a car – Lincoln Park is extremely walkable and well-connected by CTA. Ride shares (Uber/Lyft) and Divvy bikes are also great options.
Weekend Itinerary with Travel Times
Friday
- Check-in:
The Neighborhood Hotel – Lincoln Park - Afternoon: Lincoln Park Conservatory
5-min walk (0.3 miles)
Explore lush gardens and Victorian-era glasshouses. - Evening Dinner: Riccardo Enoteca 12-min walk (0.6 miles)
Classic Italian fare in a warm, intimate setting.
Saturday
- Morning Run: Lakefront Trail 10-min walk (0.5 miles) to the Fullerton entrance near Diversey Harbor
Beautiful sunrise views over Lake Michigan. Great for a 3–5 mile loop. - Late Morning: Lincoln Park Zoo 6-min walk (0.3 miles)
Free admission, family-friendly, and scenic! - Lunch: Parsons Chicken & Fish (Lincoln Park) 5-min drive / 20-min walk (1.1 miles)
Known for fried chicken, Negroni slushies, and sunny patio vibes. - Afternoon Shopping: Armitage Avenue Boutiques 6-min drive / 25-min walk (1.3 miles)
Great for unique local shopping—stop at Art Effect, All She Wrote, and Marine Layer. - Evening Entertainment: The Second City Comedy Club 8-min drive / 30-min walk (1.7 miles)
Legendary improv theater—book in advance!
Sunday
- Morning Brunch: Jam ’n Honey or Blue Door Farm Stand 5–8-min walk (0.4–0.5 miles)
Casual, kid-friendly brunch spots with local flair. - Late Morning: Chicago History Museum 4-min drive / 15-min walk (0.8 miles)
Learn about the city’s deep history near the Gold Coast. - Afternoon: North Avenue Beach 15-min walk (0.8 miles)
Great place to relax before heading out. Grab ice cream or a drink near Castaways.
Optional Add-ons (If You Have Time)
- Lincoln Park Farmers Market (Sat AM) 6-min walk (0.3 miles) at Lincoln Common (spring–fall)
- Wrightwood 659 (architectural gallery) 3-min drive / 10-min walk (0.5 miles) – check schedule for exhibitions
While we’re intrigued by the concept of travel assisted by ChatGPT, we’re still all about tapping humans first for the best travel gems and reliable advice. The Neighborhood Hotel team loves answering small or large questions as you plan your journey. We’re passionate about our 4 locations and know each city and town very well. Drop us a line and let us know how we can help!
About The Neighborhood Hotel
The Neighborhood Hotel was founded in 2020 by Jonathan Gordon — a travel enthusiast who enjoys spaces that inspire, comfort and fuel. Each suite is well equipped for short and longterm stays (i.e. kitchens, laundry, etc.). The Neighborhood Hotel transforms old buildings with compelling history into well outfitted apartment style hotels that honor the old while representing the now. The vibe is fresh and fun with rooms that are stocked to support everyone from the homebody to the adventurer. The hotels provide a basecamp for the explorer and a sanctuary for the traveler who needs to recharge, reset or just chill. The suites are simple and clean, punctuated with accents that bring the right amount of pop. The Neighborhood Hotel has locations in Chicago: Lincoln Park, Little Italy, West Loop (2025 opening) and Southwest Michigan: New Buffalo and Grand Beach.
Read about us in Architectural Digest, Midwest Living and CN Traveler!
Connect with @the.neighborhood.hotel on Instagram and LinkedIn!
