AI Thinks That
What AI actually recommends — captured, ranked, kept honest.
← Chicago City Guide · things to dos · snapshot 2026-10-07

Who are the best things to dos in Chicago?

AI thinks that the top 10 things to dos in Chicago are…

How it works

We asked every big AI at once the same buyer questions, verbatim. Here’s what they actually said — the Top 10, and all 117 they named.

Top 10

#BusinessNamedNamed by
1Chicago Architecture Center River Cruise10×ChatGPT, Google AI, Perplexity
2Millennium Park and Cloud Gate (“The Bean”)8×ChatGPT, Claude, Google AI, Perplexity
3The Art Institute of Chicago7×ChatGPT, Claude, Google AI, Perplexity
4Museum Campus6×ChatGPT, Claude, Google AI, Perplexity
5Navy Pier & Lakefront Trail6×ChatGPT, Claude, Google AI, Perplexity
6Choose Chicago (The Official Tourism Board)5×ChatGPT, Claude, Google AI, Perplexity
7Chicago Cultural Center Visitor Desk4×ChatGPT, Google AI
8Field Museum, Shedd Aquarium, and Adler Planetarium4×Claude, Google AI
9Adler Planetarium3×Google AI
10Chicago Riverwalk & Architecture Boat Tour3×Claude, Google AI, Perplexity

Full ranking (117)

#BusinessNamedNamed by
1Chicago Architecture Center River Cruise10×ChatGPT, Google AI, Perplexity
2Millennium Park and Cloud Gate (“The Bean”)8×ChatGPT, Claude, Google AI, Perplexity
3The Art Institute of Chicago7×ChatGPT, Claude, Google AI, Perplexity
4Museum Campus6×ChatGPT, Claude, Google AI, Perplexity
5Navy Pier & Lakefront Trail6×ChatGPT, Claude, Google AI, Perplexity
6Choose Chicago (The Official Tourism Board)5×ChatGPT, Claude, Google AI, Perplexity
7Chicago Cultural Center Visitor Desk4×ChatGPT, Google AI
8Field Museum, Shedd Aquarium, and Adler Planetarium4×Claude, Google AI
9Adler Planetarium3×Google AI
10Chicago Riverwalk & Architecture Boat Tour3×Claude, Google AI, Perplexity
11Chicago Visitor Center at the Chicago Cultural Center3×ChatGPT
12John Hancock Center3×ChatGPT, Claude, Google AI
13Lincoln Park & Lincoln Park Zoo3×Claude, Google AI, Perplexity
14Shedd Aquarium3×Google AI
15Skydeck Chicago (Willis Tower) or 360 CHICAGO (John Hancock)3×Google AI, Perplexity
16Why call/visit them3×Claude, Google AI
17Buddy Guy's Legends2×Google AI
18Chicago Botanic Garden2×ChatGPT, Google AI
19Chicago Greeter Program2×ChatGPT
20Chicago River Architecture Cruise2×Google AI, Perplexity
21Chicago-Style Hot Dogs & Italian Beef2×Google AI
22Deep-Dish Pizza2×Google AI
23Indiana Dunes National Park & State Park2×ChatGPT, Google AI
24Lake Michigan or Chicago River boat tour2×Perplexity
25Morton Arboretum2×ChatGPT, Google AI
26Museum of Science and Industry (MSI)2×Claude, Google AI
27Oak Park, Illinois2×ChatGPT, Google AI
28Starved Rock State Park2×ChatGPT, Google AI
29The Green Mill2×Google AI
30The Second City2×Google AI
31West Loop / Fulton Market2×Google AI
32Wrigley Field2×Claude, Perplexity
33Al's Beef1×Google AI
34Alternative option1×Claude
35Al’s Beef1×Google AI
36Architectural Boat Tour1×ChatGPT
37Architecture River Cruise1×Google AI
38Baha'i House of Worship1×Google AI
39Catch a sports game1×Perplexity
40CHICAGO (John Hancock Center)1×Google AI
41Chicago food tour1×Perplexity
42CHICAGO Observation Deck1×Claude
43Comedy1×Google AI
44Comedy Clubs1×Google AI
45Concierge at Your Hotel1×ChatGPT
46Crown Fountain1×Claude
47Day Trips & Nearby Attractions1×ChatGPT
48Education Center1×ChatGPT
49Eventbrite or Meetup1×ChatGPT
50Explore Lincoln Park1×Perplexity
51Explore the Art Institute of Chicago1×Perplexity
52Food & Neighborhoods1×Claude
53Friends or Family in Chicago1×ChatGPT
54Garfield Park Conservatory1×Google AI
55Geneva & St. Charles along the Fox River1×Google AI
56Getting there1×Google AI
57Giordano's1×Google AI
58Giordano’s1×Google AI
59Go up the Willis Tower Skydeck or 360 CHICAGO1×Perplexity
60Harley-Davidson Museum1×Google AI
61Historic Galena, IL1×ChatGPT
62Hyde Park1×Perplexity
63Iconic Chicago Food1×Google AI
64Iconic Landmarks & Sights1×Google AI
65Illinois Office of Tourism's Chicago office1×Claude
66In the City1×Claude
67Jazz & Blues1×Google AI
68Kingston Mines1×Google AI
69Lakefront Trail & Beaches1×Google AI
70Live Blues & Jazz1×Google AI
71Live music and nightlife1×Perplexity
72Local Tour Companies1×ChatGPT
73Lou Malnati's1×Google AI
74Lou Malnati’s1×Google AI
75Milwaukee Art Museum1×Google AI
76Milwaukee, Wisconsin1×Google AI
77Mr. Beef1×Google AI
78Music & Entertainment1×Google AI
79Nearby day trips1×Perplexity
80Neighborhood and food tours1×Perplexity
81Neighborhood Exploring1×Google AI
82Obama Presidential Center1×ChatGPT
83Online Resources1×ChatGPT
84Pequod's Pizza1×Google AI
85Pequod’s Pizza1×Google AI
86Pilsen1×Google AI
87Popular Things to Do in Chicago1×ChatGPT
88Portillo's1×Google AI
89Portillo’s1×Google AI
90Six Flags Great America1×ChatGPT
91Spend time at Museum Campus1×Perplexity
92Stroll Michigan Avenue and the Magnificent Mile1×Perplexity
93Studio1×Google AI
94Take an architecture river cruise1×Perplexity
95The 360 Chicago Observation Deck or Skydeck Willis Tower1×Claude
96The 606 & Neighborhood Food Tours1×Google AI
97The Magnificent Mile1×Google AI
98Third Ward1×Google AI
99Top Recommended Things to Do in Chicago1×Google AI
100Try Chicago food1×Perplexity
101Unique Experiences1×ChatGPT
102United Center1×Claude
103Unity Temple1×Google AI
104Visit Millennium Park1×Perplexity
105Visit Navy Pier1×Perplexity
106Walk or bike the Lakefront Trail1×Perplexity
107Walk the Chicago Riverwalk1×Perplexity
108Website / Contact1×Google AI
109Website / Phone1×Google AI
110Who to Call1×ChatGPT
111Why go1×Google AI
112Wicker Park & Logan Square1×Google AI
113Willis Tower Skydeck1×Claude
114Within Chicago1×ChatGPT
115World-Class Museums1×Google AI
116Wrigleyville / Lakeview1×Google AI
117Your Hotel Concierge (or a *Les Clefs d'Or* Concierge)1×Google AI

How this list was made

When2026-10-07 — a single snapshot. Engines5 queried; returned answers: ChatGPT, Claude, Google AI, Perplexity. Prompts3 buyer questions, asked verbatim; every engine got all. Answers12 captured verbatim (engine + timestamp), nothing edited. Rankingby number of mentions across all answers; ties broken by engines naming it. Mentions ≠ quality. Coverage117 businesses named in total. Independencenothing bought or placed; Memeador is not in the ranking.

Prompts asked

  1. “Who are the best things to dos in Chicago, Illinois?”
  2. “Can you recommend a good things to do near Chicago, Illinois?”
  3. “I'm looking for a good things to do in Chicago, Illinois. Who should I call, and why?”

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