From Chat to Checkout: The AI Innovations Making Holiday Shopping Smarter (Part II)

As we move through Cyber Week, or the epicenter of the busiest shopping period of the year, it’s the ideal time for the second article in our “Chat to Checkout” series. In this two-part series, we flip the lens: rather than looking at how AI shapes insights about consumers, we examine how it is reshaping the decisions consumers make themselves.

In 2024, half of the year’s most active e-commerce days fell between Black Friday and Cyber Monday (J.P. Morgan), and that’s layered on top of the annual Thanksgiving in-store grocery shopping rush. If there’s ever a time when shopping trends becomes visible in real time, the final weeks of November usually take the prize.

The holiday season has long been retail’s proving ground for innovation. The sheer scale invites experimentation: in 2024, UK shoppers spent an estimated £88 billion (Statista), and U.S. holiday sales for 2025 are forecast to reach $1.62 trillion (Forbes).

AI Chat Becomes the New Shopping Hub

This season there’s been a rapid shift by retailers toward agentic commerce. Platforms like ChatGPT, Gemini, and Copilot have become central hubs for consumers to make shopping decisions. People use them to discover, compare, and validate choices. Over the past 2 months there’s been a surge in retailer plays to meet shoppers, exactly where they are, on AI platforms.

Recent milestones:

• September 29: OpenAI announced Instant Checkout in partnership with Etsy and Shopify, allowing users to discover and purchase products without leaving the chat. A straight line from idea to transaction.
• October 14: Walmart and OpenAI partner to create AI-first shopping experiences, which would allow customers to complete purchases from Walmart directly in ChatGPT.
• November 13: Google unveiled its “biggest upgrade to shopping” in Search AI Mode, introducing conversational product comparison, local stock checks and “Buy for me”- an autonomous purchasing feature now rolling out with partners like Wayfair, Chewy, Quince and select Shopify merchants.
• November 19: Target & Open AI announced their partnership which will embed the full Target shopping experience directly into ChatGPT. A shopper can describe a holiday movie night, receive personalised recommendations, build a basket and check out via their Target account. All inside one chat.
• November 25: OpenAI launches Shopping Research, which turns product discovery into an intentional conversation. It asks questions to understand what shoppers care about, pulls up-to-date details from high quality sources, and brings options back to customers to refine the results. It currently gives customers the links to sites with a roadmap to integrate it with ‘instant checkout’ in the future.

So what’s the rush to launch these innovations all of a sudden?

There’s the obvious reason: the holidays are the biggest retail moment of the year, a natural time to debut innovations. But there’s a deeper, more customer-led reason too: the holidays bring high stakes, complex decisions, and stress, and that’s exactly when shoppers lean on AI most (Conveo AI Shopper Study).

1. T’is the Season for Decision Fatigue

The festive months compress the largest number of shopping decisions into the shortest window. Gift lists, personal purchases, meal planning, hosting, and travel arrangements all collide. Budgets are tighter. Emotions are higher. Social expectations loom larger.

AI fits seamlessly into this moment. Shoppers use tools like ChatGPT, Gemini, and Copilot to generate ideas, plan events, reduce complexity, and double-check their thinking. The more stressful the decision, the more likely they are to lean on AI.

A key driver of this is the conversational format: instead of rigid search queries and endless scrolling, people can simply describe what they need in natural language - gifts for a sister training for a marathon, or appetizers for a group with complex dietary requirements. As Target’s Chief Information and Product Officer Prat Vemana put it, the goal is to make the experience feel “as natural, helpful and inspiring as chatting with a friend.”

That may sound ambitious, but our recent Conveo study - with 330 consumers across eight markets - shows that shoppers already treat AI as equal to, and in many cases better than, human advice. AI recommendations are five times more popular than store staff or online reviews, and twice as popular as family and friends. People are leaning towards AI recommendations because it delivers tailored, context-aware recommendations that account for their specific needs and pain points.

2. The Golden Triangle of AI Adoption: Trust, Transparency & Personalization

If decision fatigue is the demand-side reason shoppers turn to AI during the holidays, the supply-side reason these new tools work is the “golden triangle” that underpins AI shopping adoption: personalization, trust, and transparency. Get these three right, and AI becomes a default shopping companion. Misjudge any one of them, and adoption stalls.

‘Personalized recommendations’ emerged as the top “job to be done” by AI in our research. When shoppers feel that AI understands their context - their needs, constraints, preferences, and pain points - and offers tailored advice, they reflect on the experience with positivity.

“My main concern, when I'm running, is the footwear… I asked ChatGPT to describe models of Salomon trail shoes for women. It helped me determine my choice, and I purchased it the same day.” (Female, 39, France)

“I was looking for a mini refrigerator… AI helped guide my choice, provided a pros-and-cons chart, and introduced a brand I hadn't initially considered. I was very happy with my decision.” (Female, 47, US)

“I spent days searching for travel accommodation… AI found an Airbnb I hadn’t considered that met all my needs, and that’s the one I booked. I technically put it in a cart, if you will.” (Male, 51, US)

But while personalization is what shoppers experience, trust is what makes them comfortable relying on AI in the first place. In our study, trustworthiness (46%) was the top attribute consumers associated with AI - well ahead of accuracy (23%), incompleteness (14%), or bias (12%). It’s also why 72% of shoppers are comfortable letting AI use personal data to improve recommendations.

Interviews make it clear that shoppers treat AI as a safer, more objective, and more patient advisor than turning to other people.

“I trust it more than store staff or friends who don’t know as much about the domain… AI is unbiased, does factual research, finds features matching my requirements, and gives facts instead of opinions.” (Male, 27, UK)

“It’s neutral, not paid by any brand… its recommendations are trustworthy.” (Female, 33, Brazil)

Weaving the triangle together is transparency. Shoppers want AI to show its reasoning, cite sources, compare options clearly, and avoid hidden motives. Generic, ad-like, or unexplained suggestions are instant deal-breakers.

“[I’d like] recommendations to be honest and transparent. Show me why a product fits my needs, not just push ads. If it feels personalized and trustworthy, I'll be more likely to buy.” (Male, 26, France)

OpenAI’s new Shopping Research feature is a textbook example of a company leaning into this golden triangle. It adapts recommendations to the individual user over time, pulls from high-quality sources, avoids low-quality or spammy sites, and shows its work. In doing so, it strengthens the three foundations that will define AI shopping as chat-to-checkout experiences continue to scale.

3. The AI Holiday Helper: From Gifting to Groceries

During the holidays, AI will show its impact most clearly in two high-pressure missions: gifting and grocery.

Gifting

The categories consumers most often use AI for - electronics and durables (17%), travel and experiences (16%), food and beverage (15%), personal care and wellness (14%), and apparel (12%) - map almost perfectly to holiday gifting.

Gifting is the most emotionally loaded mission of the season. People want to be thoughtful and original, but figuring out what to buy for everyone can be overwhelming. AI steps in as a knowledgeable advisor, translating simple descriptions of recipients, relationships, and budgets into tailored, meaningful options.

“I did use it for gifting choices… it presented me with a set of suggestions … along with the various Amazon links… I was able to click and then look at various varieties and go forward with my buying process.” (Female, 31, India)

Whether finding the right coffee machine for a parent or partner, building a personalized beauty routine for your own wish list, or choosing a client-appropriate chocolate box, AI helps shoppers weigh trade-offs, surface alternatives, and simplify decisions.

Grocery

AI is also shifting from something used for complex, planning-heavy purchases to an everyday shopping companion, particularly in Food & Beverage - one of the most consulted categories.

“AI helped me choose more affordable brands of acceptable quality… I had enough money for other products… a very positive experience.” (Female, 42, Mexico)

“AI helped me choose the healthiest options based on images and labels… saved time and effort.” (Male, 49, Brazil)

When we drill into what drives consumers to consult AI for grocery decisions, it’s recipe inspiration, shopping list generation, substitution suggestions, and confident discovery of new brands.

With that in mind, holiday grocery - another high-stakes mission, with more people to feed, more recipes to plan, and more dietary needs to consider - is also likely to be heavily influenced by AI. People who usually cook simple meals may feel empowered to attempt more ambitious menus, with AI acting as a trusted planning partner. The outcome: reduced stress, optimised budgets, more creative meals and new ingredients/products/ brands experimented with.

In Closing

For insight and marketing teams, this shift is already reshaping how consumers discover, evaluate, and buy. The holiday season compresses the widest range of shopping missions into the shortest window, making it the clearest real-world test of AI’s influence. What happens now becomes the blueprint for 2026. If instant checkout proves its value in the U.S., expect it to scale globally. If partnerships like Target × OpenAI perform well, more retailers will inevitably follow.

One dynamic to watch closely is how trust evolves as Google, OpenAI, Microsoft and major retailers deepen their partnerships. Increased commercial integration may raise shopper sensitivity to bias or commercial steering - and if trust slips, we could see consumer sentiment follow suit.

The chat-to-checkout journey isn’t coming - it’s here. The influence of AI on shopping is groundbreaking, and brands will need to adapt fast. This season, AI might just be the best (digital) shopping assistant you never knew you needed.

“The findings from our AI Shopper Study reveal that the AI-powered shopping revolution is happening now, rapidly. People put more trust in AI for recommendation because it is perceived as more complete, objective and convivial. Brands need to act today. Those that don’t risk being left behind”, shares Niels Schillewaert, Conveo Head of Research and Methodologies.

Keen to hear the wider findings from the AI-Powered Shopper Study? Conveo will be hosting an online expert session ‘From chat to checkout: The rise of the AI-poweredshopper’ on 3rd December at 4 PM GMT | 11 AM EST. Register here to join the session - we’d love to see you there!