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Live · refreshed weeklyUpdated May 18, 2026
AI Hotel Landscape
How leading AI assistants recommend hotels — 616 prompts across 56 destinations, refreshed every Monday.
Data is directional. Some prompts retry due to upstream variance, so absolute counts can shift ±5% week to week.
DESTINATION
Hotels in Chicago
What 6 AI assistants say when asked about hotels in Chicago, US. 11 prompts asked, week of May 18, 2026.
194
Distinct hotels
1,273
Total mentions
6/6
AIs with data
Where AIs send users for Chicago
167 hotel links across 27 properties, all 6 AI assistants combined
Direct 88%OTA 9%Other 3%
1 destinations across 1 countrieseuropeamericasasiaafricaoceania
COMPARE MODELS
Which hotels does each AI recommend in Chicago?
Top hotels mentioned across the 11 weekly prompts for Chicago. Each column shows how often that AI named the hotel. Bold + purple = that AI's top pick.
Top hotel per AI assistant — Chicago
| Assistant | #1 hotel | Chain | Mentions | |
|---|---|---|---|---|
| ChatGPT | Wynn Las Vegas | — | 8 | US deep dive → |
| Gemini | Hotel Monteleone | — | 8 | US deep dive → |
| Perplexity | Hotel Monteleone | — | 6 | US deep dive → |
| Grok | Hotel Monteleone | — | 9 | US deep dive → |
| Copilot | ARIA Resort & Casino | — | 7 | US deep dive → |
| Google AI Mode | The Roosevelt New Orleans, A Waldorf Astoria Hotel | Hilton | 6 | US deep dive → |
Hotel × AI matrix — top 15 hotels mentioned for Chicago
| Hotel | Chain | ChatGPT | Gemini | Perplexity | Grok | Copilot | Google AI Mode | Total |
|---|---|---|---|---|---|---|---|---|
| Hotel Monteleone | — | 7 | 8 | 6 | 9 | 4 | 5 | 39 |
| Wynn Las Vegas | — | 8 | 5 | 5 | 6 | 6 | 5 | 35 |
| The Langham, Chicago | Langham | 8 | 6 | 3 | 5 | 6 | 3 | 31 |
| Bellagio Hotel & Casino | — | 7 | 4 | 4 | 4 | 4 | 5 | 28 |
| The Roosevelt New Orleans, A Waldorf Astoria Hotel | Hilton | 6 | 3 | 5 | 4 | 4 | 6 | 28 |
| The Cosmopolitan of Las Vegas | — | 6 | 6 | 2 | 5 | 6 | 3 | 28 |
| The Venetian Las Vegas | Las Vegas Sands | — | 3 | 5 | 5 | 7 | 4 | 24 |
| 1 Hotel South Beach | 1 Hotels | 7 | 3 | — | 5 | 3 | 3 | 21 |
| The Beverly Hills Hotel | — | 4 | 4 | 2 | 4 | 3 | 4 | 21 |
| The Peninsula Chicago | Peninsula | 5 | 4 | — | 3 | 5 | 3 | 20 |
| The Ritz-Carlton, San Francisco | Marriott | 6 | 2 | — | 3 | 3 | 5 | 19 |
| The Newbury Boston | — | — | 5 | 2 | 3 | 5 | 4 | 19 |
| The Setai, Miami Beach | — | 5 | 4 | — | 5 | 4 | — | 18 |
| Hotel Miami | — | 4 | 4 | 2 | 3 | 3 | 2 | 18 |
| Boston Harbor Hotel | — | 4 | 2 | — | 4 | 4 | 3 | 17 |
Hotel Monteleone has the broadest consensus — mentioned by 6 of 6 AIs.
PROMPTS
The 11 prompts we asked about Chicago
Same 11 question patterns ask about every destination — persona (couples, families, solo, business), budget (luxury, mid, budget), and zoom (city-wide, neighborhood, landmark).
affordable hotels in Chicago under $200
budget: budgetzoom: wide
luxury hotels in Chicago
budget: luxuryzoom: wide
best hotels in Chicago for solo travelers
persona: solo_leisurezoom: wide
hotels near Millennium Park, Chicago
zoom: near
best hotels in River North, Chicago
zoom: near
best hotels in Chicago for business travelers
persona: solo_businesszoom: wide
best hotels in Chicago
zoom: widecontrol
hotels in Chicago with rooftop pool
zoom: wide
family friendly hotels in Chicago
persona: familieszoom: wide
best hotels in Chicago for couples
persona: coupleszoom: wide
boutique hotels in River North, Chicago
zoom: near