Nicolas Sitter
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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.

Hotel Chicago

How 6 AI assistants recommend this property. Week of November 2, 2026. Tracked for 12 weeks.

Latest edition
1
mentions across 6 AIs
Peak
12
best week
Mentioning AIs
1/6
latest edition
Total links
52
all time
Location
820-828 S Wabash Ave, Chicago, IL 60605
PROMPTS

Where this hotel showed up

Each prompt below resolved to Hotel Chicago at least once. The "reason" is the AI's own one-line explanation when it returned the hotel in structured form.

“boutique hotels in River North, Chicago”
Chicago, US6 of 6 AIs12 weeks23 quotes
Gemini · 11-02
“A hip, tech-forward boutique hotel known for its vibrant rock-and-roll vibe and trendy craft cocktail bar in the heart of River North.”
Gemini · 10-19
“A hip, tech-forward boutique hotel centrally located in River North offering quirky style and great craft cocktails.”
Gemini · 08-31
“A tech-forward and trendy boutique option located right in the heart of River North steps from the Magnificent Mile.”
Gemini · 08-24
“A tech-forward, stylish lifestyle boutique hotel tailored for independent travelers looking for vibrant and unconventional design.”
Google AI Mode · 07-27
“A unique, art-focused boutique hotel offering a blend of contemporary art gallery and luxury accommodation.”
Perplexity · 07-27
“Playful, tech-forward boutique property known for creative rooms and location near River North.”
“best hotels in Chicago for solo travelers”
Chicago, US4 of 6 AIs8 weeks10 quotes
ChatGPT · 08-03
“Historic hotel with vibrant social spaces directly across from Millennium Park.”
Copilot · 07-13
“Stylish and budget-friendly with a prime location near Millennium Park for easy solo exploring.”
Copilot · 07-06
“A historic, centrally located hotel offering lively dining and rooftop spaces great for solo exploration.”
Google AI Mode · 07-06
“Provides affordable, boutique-style private and shared rooms in a very central, walkable neighborhood”
ChatGPT · 06-29
“Historic landmark hotel facing Millennium Park with vibrant lobby bars and social spaces that suit solo travelers who enjoy atmosphere and design.”
ChatGPT · 06-22
“Historic boutique hotel directly across from Millennium Park with lively social spaces and excellent walkability for solo sightseeing.”
“hotels near Millennium Park, Chicago”
Chicago, US4 of 6 AIs13 weeks25 quotes
Google AI Mode · 07-27
“Offers upscale, boutique styling just steps north of Millennium Park.”
Google AI Mode · 07-20
“A boutique hotel located just north of Millennium Park, offering easy access to the park and the Chicago Riverwalk.”
Copilot · 07-13
“A boutique luxury hotel just a short walk from Millennium Park.”
Copilot · 07-13
“Directly across from Millennium Park with historic architecture and top-rated service.”
Google AI Mode · 06-29
“An upscale boutique hotel located just across the river, offering easy access to the park and luxury amenities.”
ChatGPT · 06-22
“Located directly across from Millennium Park, this historic boutique hotel offers one of the closest and most iconic stays with unique architecture and rooftop dining.”
“best hotels in River North, Chicago”
Chicago, US3 of 6 AIs8 weeks9 quotes
ChatGPT · 09-21
“A boutique hotel with a distinctive personality, energetic atmosphere, and strong River North location.”
Google AI Mode · 07-06
“A unique boutique hotel offering a curated art experience in a vibrant part of River North.”
ChatGPT · 06-29
“Fun , tech-forward boutique hotel with a unique atmosphere and craft cocktail bar.”
ChatGPT · 06-15
“A quirky, tech-forward boutique hotel that provides strong value and personality in a central River North location.”
ChatGPT · 06-08
“A creative boutique hotel offering strong value and a distinctive local character.”
ChatGPT · 06-01
“Tech-forward boutique hotel popular with travelers seeking a fun and affordable River North stay.”
“best hotels in Chicago”
Chicago, US3 of 6 AIs7 weeks7 quotes
ChatGPT · 09-14
“A historic boutique hotel across from Millennium Park with distinctive design and lively dining venues.”
Google AI Mode · 07-13
“A highly-rated boutique hotel in a historic Venetian Gothic building directly across from Millennium Park.”
ChatGPT · 06-15
“Features distinctive historic character and an unbeatable location across from Millennium Park.”
ChatGPT · 05-18
“Converted historic building with stylish, playful interiors and rooftop bar overlooking Millennium Park.”
ChatGPT · 05-11
“Historic club turned stylish hotel near Millennium Park with rooftop bar.”
Perplexity · 05-04
“Boutique feel with design-forward rooms and proximity to top eateries and landmarks.”
“affordable hotels in Chicago under $200”
Chicago, US3 of 6 AIs6 weeks9 quotes
Gemini · 07-13
“This trendy, hip boutique hotel offers budget-friendly rates consistently under $200 right in the heart of River North, just blocks from the Magnificent Mile.”
Google AI Mode · 07-06
“Provides stylish private and shared rooms in a central location often catering to budget-conscious travelers.”
Google AI Mode · 07-06
“A uniquely designed hotel located in Lincoln Park that often offers rates significantly lower than downtown options.”
Perplexity · 06-22
“Central Loop location with stylish rooms at affordable rates often under $200.”
Perplexity · 06-15
“Located in the Loop with easy access to Millennium Park and affordable rates often under $200.”
Gemini · 06-15
“This hip, budget-friendly boutique hotel features high-tech amenities and an ultra-convenient location just a few blocks away from the Magnificent Mile.”
“best hotels in Chicago for couples”
Chicago, US2 of 6 AIs3 weeks3 quotes
ChatGPT · 10-19
“Historic character, distinctive interiors, and a Millennium Park location offer a memorable, less conventional romantic stay.”
ChatGPT · 10-12
“Historic character and the Cindy's rooftop offer a distinctive, memorable romantic experience.”
Perplexity · 07-27
“Chic boutique vibe with playful design and central downtown access ideal for couples exploring the city.”
“best hotels in Chicago for business travelers”
Chicago, US1 of 6 AIs2 weeks2 quotes
Perplexity · 05-25
“Boutique option with flexible workspaces and strong meeting capabilities in a convenient downtown venue.”
Perplexity · 04-27
“Central location with contemporary work-friendly rooms and flexible event spaces.”
“hotels in Chicago with rooftop pool”
Chicago, US1 of 6 AIs1 week1 quote
ChatGPT · 05-18
“Historic hotel with a rooftop pool and vibrant social spaces.”
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.

03504-2705-0405-1806-0106-1506-2206-2907-0607-1307-2710-19Nov 2026mentions
ChatGPTGeminiPerplexityGrokCopilotGoogle AI Mode

Weekly until 19 Oct 2026, monthly from November 2026

WeekChatGPTGeminiPerplexityGrokCopilotGoogle AI ModeTotal
November 2, 2026—1————1
October 19, 2026—1————1
July 27, 2026——2——24
July 13, 2026————3—3
July 6, 2026————257
June 29, 2026—————22
June 22, 2026——1———1
June 15, 20264—2———6
June 1, 2026————3—3
May 18, 2026————3—3
May 4, 2026—42——511
April 27, 20263—5—2212
See live ChatGPT data →Methodology