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Weekly until 19 Oct 2026, monthly from November 2026November 2026 edition
AI Hotel Landscape
How leading AI assistants recommend hotels: 616 prompts across 56 destinations, a monthly edition checked before it is published.
Data is directional. Some prompts retry due to upstream variance, so absolute counts can shift ±5% between editions.
The Robey
How 6 AI assistants recommend this property. Week of November 2, 2026. Tracked for 18 weeks.
Latest edition
4
mentions across 6 AIs
Peak
6
best week
Mentioning AIs
2/6
latest edition
Total links
62
all time
Location
2018 W North Ave, Chicago, IL 60647
PROMPTS
Where this hotel showed up
Each prompt below resolved to The Robey at least once. The "reason" is the AI's own one-line explanation when it returned the hotel in structured form.
“best hotels in Chicago for solo travelers”Chicago, US6 of 6 AIs20 weeks28 quotes
“best hotels in Chicago for solo travelers”
Chicago, US6 of 6 AIs20 weeks28 quotes
Google AI Mode · 11-02
“An Art Deco landmark in creative Wicker Park with easy subway access, perfect for solo travelers seeking a trendy neighborhood vibe off the beaten path.”
Google AI Mode · 10-19
“Situated right outside the Blue Line in vibrant Wicker Park, it delivers an artsy neighborhood experience away from the heavy downtown crowds.”
Google AI Mode · 10-12
“This vibrant art deco boutique hotel provides a social, neighborhood-centric experience right next to transit in Wicker Park.”
Gemini · 10-05
“Situated in vibrant Wicker Park, this trendy art deco hotel features a lively rooftop lounge perfect for solo travelers looking to socialize.”
Google AI Mode · 10-05
“Housed in a striking Art Deco tower in Wicker Park, it offers a hip neighborhood vibe steps from the Blue Line and vibrant local nightlife.”
Google AI Mode · 09-07
“An Art Deco masterpiece in artsy Wicker Park providing a neighborhood-focused solo getaway with stunning rooftop views and direct Blue Line access.”
“hotels in Chicago with rooftop pool”Chicago, US6 of 6 AIs27 weeks92 quotes
“hotels in Chicago with rooftop pool”
Chicago, US6 of 6 AIs27 weeks92 quotes
Google AI Mode · 11-02
“This upmarket art deco hotel features a stunning rooftop pool with panoramic views over Wicker Park.”
Gemini · 11-02
“Located in an iconic Art Deco tower in Wicker Park, it features an intimate rooftop pool and lounge area overlooking the skyline.”
Google AI Mode · 10-19
“Situated in an striking art deco landmark building in Wicker Park, it features a unique triangular rooftop pool with sweeping views.”
ChatGPT · 10-19
“This Art Deco boutique hotel has a seasonal outdoor rooftop pool with downtown skyline views in the lively Wicker Park neighborhood.”
Gemini · 10-19
“Housed in a striking Art Deco tower in Wicker Park with a popular rooftop pool and sweeping 180-degree city views.”
Google AI Mode · 10-12
“This upmarket art deco hotel features the popular seasonal Solana rooftop pool deck with sweeping skyline views.”
“best hotels in Chicago”Chicago, US3 of 6 AIs10 weeks14 quotes
“best hotels in Chicago”
Chicago, US3 of 6 AIs10 weeks14 quotes
Gemini · 11-02
“A trendy art-deco design hotel providing a vibrant neighborhood experience at the nexus of Wicker Park and Bucktown.”
Gemini · 10-19
“An Art Deco boutique hotel providing trendy, design-forward accommodations in the heart of Wicker Park.”
ChatGPT · 09-21
“A distinctive design-focused hotel in Wicker Park offering neighborhood character, rooftop spaces, skyline views, and easy access to local restaurants and nightlife.”
ChatGPT · 09-07
“A stylish boutique hotel in Wicker Park that offers a more neighborhood-focused Chicago experience.”
Google AI Mode · 08-31
“A vibrant art deco boutique hotel featuring an amazing rooftop lounge and local Wicker Park charm.”
Google AI Mode · 08-31
“A vibrant art deco boutique hotel featuring an amazing rooftop lounge and local Wicker Park charm.”
“best hotels in Chicago for couples”Chicago, US2 of 6 AIs4 weeks4 quotes
“best hotels in Chicago for couples”
Chicago, US2 of 6 AIs4 weeks4 quotes
ChatGPT · 05-25
“A boutique Art Deco hotel in Wicker Park offering a cozy, local, and intimate experience for couples.”
ChatGPT · 05-18
“Art Deco meets modern loft vibes with rooftop pool and private balconies, great for young or artsy couples.”
ChatGPT · 05-11
“A stylish boutique hotel in Wicker Park offering a more intimate and trendy couples getaway.”
Perplexity · 04-27
“Boutique vibe with stylish rooms and standout rooftop views for a chic couples’ escape.”
“boutique hotels in River North, Chicago”Chicago, US1 of 6 AIs5 weeks5 quotes
“boutique hotels in River North, Chicago”
Chicago, US1 of 6 AIs5 weeks5 quotes
Perplexity · 08-17
“Art deco-inspired boutique with rooftop pool and stylish rooms near River North.”
Perplexity · 08-10
“Stylish boutique hotel in a landmark building with a rooftop pool and vibrant dining scene nearby.”
Perplexity · 08-03
“Art deco-inspired boutique hotel with a rooftop pool and stylish facilities in a trendy neighborhood near River North.”
Perplexity · 07-27
“Art Deco-inspired boutique hotel with vibrant nightlife and distinctive rooms.”
Perplexity · 07-20
“A stylish, art-deco boutique with a rooftop pool and vibrant dining options, close to River North vibe.”
“affordable hotels in Chicago under $200”Chicago, US1 of 6 AIs1 week1 quote
“affordable hotels in Chicago under $200”
Chicago, US1 of 6 AIs1 week1 quote
Perplexity · 06-22
“Boutique hotel with competitive nightly rates and easy access to downtown attractions.”
PER-AI MENTIONS
Mentions per AI assistant, by edition
One line per AI. Each point is the number of times the assistant named this property across the 11 prompt templates for its city, that week.
ChatGPTGeminiPerplexityGrokCopilotGoogle AI Mode
Weekly until 19 Oct 2026, monthly from November 2026
| Week | ChatGPT | Gemini | Perplexity | Grok | Copilot | Google AI Mode | Total |
|---|---|---|---|---|---|---|---|
| November 2, 2026 | — | 2 | — | — | — | 2 | 4 |
| October 19, 2026 | — | 2 | — | — | — | 2 | 4 |
| October 12, 2026 | — | — | — | — | — | 2 | 2 |
| October 5, 2026 | — | 2 | — | — | — | 2 | 4 |
| September 7, 2026 | — | — | — | — | — | 2 | 2 |
| August 31, 2026 | — | — | — | — | — | 6 | 6 |
| August 17, 2026 | — | 2 | — | — | — | 2 | 4 |
| August 10, 2026 | — | — | 2 | — | — | 2 | 4 |
| August 3, 2026 | — | — | 2 | — | — | — | 2 |
| July 27, 2026 | — | — | 2 | — | 2 | — | 4 |
| June 29, 2026 | — | 2 | — | — | — | — | 2 |
| June 22, 2026 | — | — | 3 | — | — | — | 3 |
| June 15, 2026 | — | — | — | — | 2 | — | 2 |
| May 25, 2026 | 4 | — | — | — | 2 | — | 6 |
| May 18, 2026 | 4 | 2 | — | — | — | — | 6 |
| May 11, 2026 | 4 | — | — | — | — | — | 4 |
| May 4, 2026 | — | — | — | — | 1 | — | 1 |
| April 27, 2026 | 2 | — | 2 | — | — | 2 | 6 |
LINK MIX
Where AIs send users for this hotel
When the AI links the hotel, where does it point — the hotel's own site (direct), an OTA like Booking.com, a chain page like Marriott.com, or something else?
All time (62 links)
Direct 90%OTA 3%Google Travel 3%Other 3%
Week-by-week
November 2, 20262 links / 4 mentions
October 19, 20262 links / 4 mentions
October 12, 20262 links / 2 mentions
October 5, 20264 links / 4 mentions
September 7, 20262 links / 2 mentions
August 31, 20266 links / 6 mentions
August 17, 20264 links / 4 mentions
August 10, 20264 links / 4 mentions
August 3, 20262 links / 2 mentions
July 27, 20264 links / 4 mentions
June 29, 20262 links / 2 mentions
June 22, 20263 links / 3 mentions
June 15, 20262 links / 2 mentions
May 25, 20266 links / 6 mentions
May 18, 20266 links / 6 mentions
May 11, 20264 links / 4 mentions
May 4, 20261 links / 1 mentions
April 27, 20266 links / 6 mentions
Direct (own site + chain page) OTA Other