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.

Freehand Chicago

How 6 AI assistants recommend this property. Week of November 2, 2026. Tracked for 23 weeks.

Latest edition
2
mentions across 6 AIs
Peak
13
best week
Mentioning AIs
2/6
latest edition
Total links
118
all time
Location
19 E Ohio St, Chicago, IL 60611
PROMPTS

Where this hotel showed up

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

“affordable hotels in Chicago under $200”
Chicago, US6 of 6 AIs21 weeks58 quotes
Google AI Mode · 11-02
“A trendy, budget-friendly boutique hostel hybrid situated right in the vibrant River North neighborhood.”
Gemini · 11-02
“A chic, design-forward boutique hybrid hotel offering budget-friendly private rooms in the heart of River North.”
Gemini · 09-28
“A stylish, bohemian-chic hotel located in River North offering affordable rates well under $200 per night.”
Gemini · 08-31
“Offers stylish private and shared rooms in the vibrant River North neighborhood at an affordable price point.”
Gemini · 08-24
“A stylish and affordable boutique hybrid hotel located just steps away from the Magnificent Mile and River North.”
ChatGPT · 08-24
“A River North property that was mentioned as an affordable option with some dates available under $200.”
“best hotels in Chicago for solo travelers”
Chicago, US6 of 6 AIs26 weeks75 quotes
Google AI Mode · 10-19
“Offering both private rooms and upscale social spaces, it provides a lively, budget-friendly boutique hostel atmosphere ideal for meeting people.”
ChatGPT · 10-19
“Its cocktail bar and lively communal atmosphere give solo travelers easy chances to socialize, with private rooms available.”
ChatGPT · 10-12
“It is a hotel-hostel hybrid in River North with shared and private rooms and a lively bar, which makes it easy for solo travelers to meet people.”
Copilot · 10-05
“Trendy hostel-style hotel with social spaces perfect for meeting other travelers.”
Google AI Mode · 09-28
“This bohemian-chic hybrid hotel offers both private rooms and social shared spaces, making it exceptionally easy for solo travelers to meet people in a vibrant River North setting.”
Gemini · 09-28
“This bohemian-chic hotel offers both shared and private rooms, making it an affordable and social option for solo travelers looking to meet people.”
“boutique hotels in River North, Chicago”
Chicago, US4 of 6 AIs15 weeks20 quotes
Gemini · 10-05
“A bohemian-chic boutique hotel and hostel set in a classic vintage building right in the River North neighborhood.”
Gemini · 09-28
“This bohemian-chic boutique hotel is located right in the heart of River North, offering stylish quarters and a vibrant social atmosphere.”
ChatGPT · 09-28
“A casual, design-focused option in a restored 1920s building offering a social atmosphere and both private and shared accommodations.”
ChatGPT · 09-21
“An artsy, social hotel-hostel hybrid in a restored 1920s building with design-forward rooms, a café, and the Broken Shaker bar.”
Gemini · 09-21
“Housed in a classic 1927 building, this bohemian-chic boutique hotel offers stylish quarters right in the heart of the neighborhood.”
Google AI Mode · 09-07
“A bohemian-chic boutique property housed in a restored 1927 Art Deco building featuring the acclaimed Broken Shaker bar.”
“hotels near Millennium Park, Chicago”
Chicago, US2 of 6 AIs5 weeks5 quotes
Gemini · 10-12
“A stylish bohemian-chic property located a short distance away from Millennium Park in River North.”
Gemini · 09-28
“A stylish bohemian-chic property located in the nearby River North neighborhood close to Millennium Park.”
Gemini · 09-21
“A stylish, bohemian-chic boutique hotel situated within a short distance of Millennium Park in River North.”
Gemini · 08-17
“A stylish, bohemian-chic option for travelers looking for a unique atmosphere near downtown Chicago.”
ChatGPT · 05-11
“Trendy boutique hostel-hotel hybrid a short walk from Millennium Park.”
“best hotels in River North, Chicago”
Chicago, US2 of 6 AIs4 weeks4 quotes
Gemini · 09-28
“A trendy and vibrant boutique option featuring bohemian-chic decor and a popular cocktail bar directly in the heart of River North.”
Google AI Mode · 07-20
“Trendy, affordable, and creative boutique hotel with a lively cocktail bar, perfect for a stylish stay.”
Google AI Mode · 06-29
“Offers an upscale hostel experience with private rooms and a popular cocktail bar, making it great for trendy travelers.”
Gemini · 05-04
“Perfect for social travelers, this trendy spot offers a mix of private rooms and shared spaces along with the award-winning Broken Shaker cocktail bar.”
“best hotels in Chicago”
Chicago, US2 of 6 AIs3 weeks3 quotes
Perplexity · 07-06
“Bohemian-chic social hotel with lively common spaces, ideal for travelers seeking a social vibe.”
ChatGPT · 05-18
“Trendy, social vibe with shared and private rooms, offering style without high cost.”
ChatGPT · 05-11
“Cool hostel-hotel hybrid in River North, great for younger travelers.”
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.

03604-2705-0405-1105-1805-2506-0106-0806-1506-2206-2907-0607-1307-2007-2708-0308-1008-1708-2409-2109-2810-0510-19Nov 2026mentions
ChatGPTGeminiPerplexityGrokCopilotGoogle AI Mode

Weekly until 19 Oct 2026, monthly from November 2026

WeekChatGPTGeminiPerplexityGrokCopilotGoogle AI ModeTotal
November 2, 2026—1———12
October 19, 2026—————11
October 5, 2026—1————1
September 28, 2026—5————5
September 21, 202622————4
August 24, 2026—2———24
August 17, 2026————235
August 10, 2026—2———24
August 3, 2026——2——24
July 27, 2026—————22
July 20, 2026—2——237
July 13, 2026————2—2
July 6, 2026—2——226
June 29, 2026—————33
June 22, 2026——1—236
June 15, 2026————224
June 8, 202632———38
June 1, 2026—2——226
May 25, 2026—2——226
May 18, 202632—22—9
May 11, 202652—2—211
May 4, 202634—6——13
April 27, 202622—11—6
See live ChatGPT data →MethodologyVisit Freehand Chicago →