Sky Link Times | New York | 2025
Artificial intelligence has officially become the biggest trend of the 2025 holiday shopping season. Major retailers and tech giants — including Amazon, Walmart, Google, Target and OpenAI — are rolling out advanced AI shopping tools designed to simplify gifting, personalize recommendations and automate purchases like never before.

While AI-powered shopping is still in its early stage, this year’s assistants are far more capable than the basic chatbots of years past. The latest tools can offer detailed product suggestions, track prices, compare items and even make phone calls to local stores — all through natural, unscripted conversations.
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AI Expected to Influence $73 Billion in Global Holiday Sales
According to Salesforce, AI is expected to influence $73 billion in global holiday spending between the Tuesday before Thanksgiving and Cyber Monday — up from $60 billion last year.
Caila Schwartz, Salesforce’s Director of Consumer Insights, attributed the growth to AI-driven search tools, personalized gift guides and automated recommendations appearing across retailer websites.
However, Brad Jashinsky of Gartner believes AI’s real impact is still developing.
“Customer behavior takes a long time to change,” he said. “But the more retailers introduce these tools, the faster adoption will grow.”
Smarter Gift Discovery Through Personalized AI Tools
ChatGPT’s Personalized Buyer Guides
OpenAI has upgraded ChatGPT with advanced shopping research features powered by real product data, customer reviews and user preferences. The chatbot now generates custom buying guides, especially useful for complex categories like electronics, appliances, beauty products and sports gear.
Amazon’s Enhanced Rufus Assistant
Amazon’s AI assistant Rufus now remembers user details — such as a family’s preferences, past purchases or hobbies — and tailors product suggestions accordingly.
Google’s Natural-Language Shopping Mode
Google’s AI Mode can process very specific requests like:
“Find a warm, casual sweater for January in New York that matches skirts or jeans.”
The tool pulls answers from 50 billion product listings and generates side-by-side comparison charts.
New Era of Price-Tracking Tools
Price alerts and trackers long existed, but AI has transformed them into powerful shopping companions.
Amazon’s 90-Day Price History
Shoppers can now view a 90-day price graph for almost every product sold on Amazon and set budget-based alerts.
Google and Microsoft Copilot Trackers
Google has introduced a more detailed version of its price tracker, allowing users to monitor items by size, color and style.
Microsoft Copilot also launched its own AI-driven price monitoring system.
Experts believe these tools will pressure retailers to maintain competitive pricing, as more shoppers discover automatic alerts.
AI Takes Over Checkout and Autonomous Purchasing
ChatGPT Instant Checkout
OpenAI now allows users to buy products directly inside ChatGPT, including from Etsy sellers and Shopify brands like Glossier, Skims and Spanx.
Walmart and Target Integrations
Walmart’s partnership with OpenAI enables near-complete shopping through ChatGPT (except fresh food).
Target’s collaboration allows multi-item carts inside ChatGPT, though checkout redirects to the Target app.
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Autonomous “Buy for Me” Agents
Retailers are testing agentic AI, capable of buying items automatically when prices drop:
Amazon’s Rufus “Auto Buy” completes purchases once an item hits a user’s target price.
Google Pay’s “Buy for Me” places orders automatically for eligible retailers like Wayfair, Chewy and Quince.
Google’s AI Caller can phone physical stores to check for product availability.
These early versions hint at the future: AI that will shop independently on behalf of consumers.
A Transformational Moment for Online Shopping
Retail experts describe 2025 as a “breakthrough year” for AI-driven commerce. While adoption is still growing, the tools introduced this season show how artificial intelligence could reshape how billions of people shop in the years ahead.
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