7-Day Chicago AI Trip Planner: Validated Itinerary

3-Day Sample Itinerary

Day 1 — Arrival & Orientation
• Arrive at ORD or MDW; L train or cab to Loop (validated 45–60 min)
• Check-in; lunch at Portillo's or Lou Malnati's
• Afternoon: Millennium Park; Cloud Gate; Art Institute of Chicago
• Evening: dinner at Alinea or Girl & the Goat; Riverwalk

Day 2 — Core Experiences
• Morning: Architecture River Cruise (pre-book)
• Lunch: Deep-dish at Giordano's or Pequod's
• Afternoon: Willis Tower Skydeck; Magnificent Mile
• Evening: dinner in West Loop; jazz at Green Mill

Day 3 — Deeper Exploration
• Morning: Museum of Science and Industry or Field Museum
• Lunch: Chinatown or Pilsen
• Afternoon: Wrigley Field (tour) or Lincoln Park Zoo
• Evening: farewell dinner in Logan Square; pack for departure