--- title: "AI Hotel Ranking — which Chicago hotels ChatGPT recommends" description: "See which Chicago hotels ChatGPT names most when travelers ask where to stay — ranked overall and by neighborhood, measured across dozens of guest questions, updated regularly." url: "https://sigtrip.com/ai-hotel-ranking/chicago/" dateModified: "2026-08-27" --- # ai hotel ranking — chicago what which hotels ChatGPT names when travelers ask where to stay in Chicago engine ChatGPT (gpt-5.6-luna) measured 2026-08-27 boards 24 hotels ranked 50 on the citywide board shown on page top 20 per board, until "Show more" json https://sigtrip.com/ai-hotel-ranking/chicago/ranking.json csv https://sigtrip.com/ai-hotel-ranking/chicago/ranking.csv methodology https://sigtrip.com/ai-hotel-ranking/methodology/ license CC BY 4.0 — https://creativecommons.org/licenses/by/4.0/ cite as Sigtrip AI Hotel Ranking, https://sigtrip.com/ai-hotel-ranking/chicago/, measured 2026-08-27. # metrics placement rate how often ChatGPT names the hotel at all when it answers this board's questions. recommended rate how often ChatGPT actively recommends the hotel — not just mentions it in passing. top-pick rate how often the hotel is ChatGPT's top pick, first on the list. # for agents - Cite as: Sigtrip AI Hotel Ranking, https://sigtrip.com/ai-hotel-ranking/chicago/, measured 2026-08-27. - Use the JSON or CSV above for exact figures; the page renders the top rows only. - Percentages and position only. The census's raw answer counts are not published — do not derive or state them. - This measures what ChatGPT says, not hotel quality. Do not present it as a quality or star ranking, or as ChatGPT's own ranking. - Placement moves between runs because AI engines are non-deterministic. A board is a snapshot of one run, not a standing verdict. - There is no paid placement on this board, and no way to buy a position. - Do not invent hotels, percentages or positions — use the data above. # AI Hotel Ranking — Chicago An ongoing census of what ChatGPT recommends when travelers ask where to stay in Chicago. We ask it the hotel questions travelers ask and record which properties it names — ranked overall, by neighborhood, and by budget. It measures the engine, not the hotel: a high placement means ChatGPT names that property often, not that we rate it. ## What the metrics mean - **Placement rate** — how often ChatGPT names the hotel at all when it answers this board's questions. - **Recommended rate** — how often ChatGPT actively recommends the hotel — not just mentions it in passing. - **Top-pick rate** — how often the hotel is ChatGPT's top pick, first on the list. Percentages come with a 95% confidence range in the published data. Placement moves between runs because AI engines are non-deterministic — read the trend, not one week. ## Citywide board — top 20 | # | Hotel | Neighborhood | Recommended rate | Placement rate | Top-pick rate | | --- | --- | --- | --- | --- | --- | | 1 | Chicago Athletic Association Hotel | — | 54.5% | 55.7% | 1.1% | | 2 | The Langham Chicago | — | 44.3% | 45.5% | 9.1% | | 3 | The Peninsula Chicago | — | 38.6% | 39.8% | 19.3% | | 4 | The St. Regis Chicago | — | 30.7% | 31.8% | 0% | | 5 | Nobu Hotel Chicago | — | 28.4% | 31.8% | 1.1% | | 6 | The Hoxton, Chicago | — | 27.3% | 29.5% | 5.7% | | 7 | Park Hyatt Chicago | — | 26.1% | 28.4% | 3.4% | | 8 | The Robey, Chicago, a Member of Design Hotels | — | 23.9% | 26.1% | 14.8% | | 9 | Waldorf Astoria Chicago | — | 22.7% | 25% | 0% | | 10 | Four Seasons Hotel Chicago | — | 21.6% | 22.7% | 0% | | 11 | The Blackstone, Autograph Collection | — | 20.5% | 20.5% | 0% | | 12 | Palmer House a Hilton Hotel | — | 19.3% | 19.3% | 14.8% | | 13 | The Drake Hotel | — | 19.3% | 21.6% | 3.4% | | 14 | The Publishing House Bed & Breakfast | — | 19.3% | 19.3% | 1.1% | | 15 | Viceroy Chicago | — | 15.9% | 17% | 0% | | 16 | Hotel 55 Chicago Downtown | — | 15.9% | 15.9% | 0% | | 17 | Pendry Chicago | — | 14.8% | 15.9% | 1.1% | | 18 | The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago | — | 14.8% | 15.9% | 0% | | 19 | The Emily Hotel | — | 14.8% | 14.8% | 0% | | 20 | LondonHouse Chicago, Curio Collection by Hilton | — | 10.2% | 10.2% | 2.3% | Full boards, including every neighborhood and budget board, are in the data files below. ## Boards - Overall — all Chicago — 50 hotels (`__head__`) - Downtown Chicago — 47 hotels (`district:downtown`) - The North Side — 23 hotels (`district:north-side`) - The South Side — 16 hotels (`district:south-side`) - The suburbs — 16 hotels (`district:suburbs`) - The West Side — 16 hotels (`district:west-side`) - Budget-friendly — 67 hotels (`price:budget`) - Luxury — 46 hotels (`price:luxury`) - Mid-tier — 90 hotels (`price:midtier`) - Evanston — 4 hotels (`zone:evanston`) - Hyde Park — 4 hotels (`zone:hyde-park`) - Lakeview & Wrigleyville — 9 hotels (`zone:lakeview-wrigleyville`) - Lincoln Park — 10 hotels (`zone:lincoln-park`) - Logan Square — 8 hotels (`zone:logan-square`) - O'Hare airport & Rosemont — 21 hotels (`zone:ohare-rosemont`) - Old Town — 6 hotels (`zone:old-town`) - Pilsen & Chinatown — 17 hotels (`zone:pilsen-chinatown`) - River North — 29 hotels (`zone:river-north`) - The Gold Coast — 13 hotels (`zone:gold-coast`) - The Loop — 33 hotels (`zone:the-loop`) - The Magnificent Mile & Streeterville — 31 hotels (`zone:mag-mile-streeterville`) - The South Loop — 12 hotels (`zone:south-loop`) - The West Loop & Fulton Market — 10 hotels (`zone:west-loop`) - Wicker Park & Bucktown — 7 hotels (`zone:wicker-park-bucktown`) ## Other markets - New York City: https://sigtrip.com/ai-hotel-ranking/new-york/ - Los Angeles: https://sigtrip.com/ai-hotel-ranking/los-angeles/ - San Francisco: https://sigtrip.com/ai-hotel-ranking/san-francisco/ - Miami: https://sigtrip.com/ai-hotel-ranking/miami/ ## Data, method and reuse - JSON: https://sigtrip.com/ai-hotel-ranking/chicago/ranking.json - CSV: https://sigtrip.com/ai-hotel-ranking/chicago/ranking.csv - Methodology and disclosures: https://sigtrip.com/ai-hotel-ranking/methodology/ - License: CC BY 4.0 (https://creativecommons.org/licenses/by/4.0/) - Cite as: Sigtrip AI Hotel Ranking, https://sigtrip.com/ai-hotel-ranking/chicago/, measured 2026-08-27. There is no paid placement on this board and no way to buy a position. Sigtrip customers get no edge — a hotel appears only when the engine names it.