Did you know that 59% of leisure travelers under 45 have admitted to using generative AI to plan a trip? When it comes to traveling during holidays, Chicago is one of the best destinations in the U.S. with its festive events, dazzling holiday lights, and rich culture.
Therefore, it’s no wonder that in its annual “World’s Best Awards” survey for 2024, Travel + Leisure has ranked Chicago as the 9th best city in the country. However, the city’s popularity also means you will have to do quite a bit of planning for a vacation here, especially during the peak holiday season.
Having said that, AI can offer a personal concierge experience for your next holiday in Chicago. AI tools can help you craft personalized itineraries, plan your accommodation, and more with a simple prompt. In this article, we will discuss how you can use AI to plan a perfect trip to Chicago.
1. Prepare an Ideal Itinerary With AI Chatbots
According to Longwoods International’s American Travel Sentiment Study, 31% of American travelers are likely to use ChatGPT to plan their next trip. However, a report suggests that 13% of AI users felt that their experience with a chatbot needed to be better. The key to having a fruitful result is to be specific with your prompts, such as “Plan a five-day trip to Chicago with a family of four to enjoy holidays.”
Most chatbots allow suggestions to be refined further by asking the AI tool to swap an activity for another, look for accommodation in a better location, etc. You can ask the chatbot to add restaurant recommendations, popular Christmas attractions, an activity you are interested in, and more. This way, you can devise an itinerary that best suits your interests.
You can even ask the chatbot to suggest the best way to get around, like public transportation or Sprinter rental in Chicago. While Chicago has robust public transportation, renting a spacious vehicle will allow you to enjoy the holidays at your own pace.
According to Eminent Limo, Sprinter van rentals are perfect for various occasions, including family vacations. With spacious and comfortable ride quality, these vans offer a relaxing pace to enjoy the holiday.
2. Leverage AI to get the Best Deals on Flights and Hotel Bookings
The next step is to book hotels and flights to your destination. AI tools like Kayak and Hopper can streamline this process. These platforms use AI to analyze historical trends and predict price trends. This information will help you determine the best time to book tickets to Chicago. Tools like Price Forecast or Price Freeze are handy for booking flight tickets within your budget.
Similarly, major hotel chains have introduced AI chatbots on their apps and websites to make the whole process of booking a stay and checking in very intuitive for travelers. These chatbots are designed to answer patrons’ usual queries about bookings, amenities, nearest attractions, distance from the airport, etc.
However, it’s advised to compare the prices shown by AI with the prices listed on the official website. Moreover, even if the AI tool offers an integrated booking system, book directly through the official channels.
3. Use AI to Unearth Hidden Gems Beyond Tourist Traps
Once you have prepared an itinerary and booked tickets using AI, you can take the whole experience to the next level with personalized recommendations. These recommendations can range from restaurants and activities to finding the best route while navigating the city. The last bit is essential since Chicago is among the top ten cities globally with the highest traffic delay times.
Apps like Google Search, Yelp, OpenTable, or Time Out Chicago can leverage AI to tailor restaurant and activity suggestions based on your search history and ratings. And with AI, you can further streamline these suggestions by using filters. These include dietary preferences, budget, and interests like live music, outdoor seating, etc.
It’s advised to experiment with various AI tools and filters to discover unique experiences not listed online. Remember that the best advice often comes from locals. So, don’t hesitate to ask your hotel concierge or bartender to uncover hidden gems that AI might miss.
As you can see, AI can make planning the dream Chicago holiday much less daunting than it typically is. Ask the AI tool to generate an itinerary, suggest flights and accommodations, and recommend things to do. Take this information as the blueprint and make all your bookings through the official channels. This way, not only will you have planned a perfect vacation, but you will also practice caution against scams.
