What AI searches when asked for hotels in Chicago
Before answering a hotel question with web search, an AI assistant rewrites it into one or more searches. These are the searches it actually ran for 11 traveller prompts about Chicago, captured week after week, not autocomplete suggestions.
Explore by prompt
Percentages are shares of answers. Grok and Gemini were captured on an earlier prompt set, so most current prompts only have ChatGPT.
The searches ChatGPT ran
Most frequent first. “×3” means the same search appeared in three separate answers.
- best hotels Chicago luxury 2026×3 · last 14 Sept 2026
- best hotels Chicago×3 · last 3 Aug 2026
- best luxury hotels×2 · last 2 Nov 2026
- best hotels in Chicago×2 · last 6 Jul 2026
- best hotels downtown Chicago×1 · last 2 Nov 2026
- top-rated boutique hotels×1 · last 2 Nov 2026
- best hotels in Chicago 2026 luxury boutique top rated neighborhoods River North Loop Gold Coast×1 · last 2 Nov 2026
- best hotels in Chicago 2026 luxury boutique neighborhoods traveler reviews×1 · last 19 Oct 2026
- best hotels in Chicago 2026 luxury boutique downtown Riverwalk Magnificent Mile reviews×1 · last 13 Oct 2026
- best hotels in Chicago luxury travel×1 · last 17 Aug 2026
- best hotels Chicago luxury×1 · last 27 Jul 2026
- best hotels in Chicago 2026 luxury boutique downtown Chicago hotels×1 · last 22 Jun 2026
- best hotels in Chicago luxury hotels Chicago 2026×1 · last 15 Jun 2026
- best hotels in Chicago luxury hotels Chicago 2025×1 · last 8 Jun 2026
- Sofitel Chicago Magnificent Mile address official website×1 · last 2 Jun 2026
Showing 15 of 22 distinct searches.
Words it added to the prompt
Places and names it added
No capitalised name added in two or more answers.
Hotel topics in what it added
All Chicago prompts together
Share of answers whose searches added each topic, counting only words that were not already in the prompt.
What a Chicago hotel page can cover
The topics ChatGPT adds most often here, with what a page can do about each. These are editorial suggestions drawn from the searches, not a measured ranking effect.
- A year25% of answers
Say what is current: this year’s renovations, prices and openings, with dates on the page.
- Hotel class or style21% of answers
State your class and style plainly (five-star, boutique, historic) in text and in schema.
- Neighbourhood and location20% of answers
Name your neighbourhood and what is walkable from it, in words, not only on a map.
- Best / top18% of answers
The engine is looking for lists. Being on the editorial and booking-site lists matters as much as your own page.
- Who it is for12% of answers
Say who the hotel suits (families, couples, business) and why, with specifics.
Which hotels get named? The answers behind these searches are tracked in the AI Hotel Landscape for Chicago.
How the searches were captured and cleaned, and what is left out: method and limits. ChatGPT data runs to Nov 2026.