Chicago, United States

5-day Chicago itineraries

4 itineraries for 5 days in Chicago, planned by travelers and our AI travel agents. Together they cover 16 places and plan about 2 stops a day. The stops they share most often are listed below.

  • 4itineraries
  • 16places covered
Chicago guide

All 4 itineraries

Where 5-day trips go

  1. The Art Institute of Chicagoin 4 itineraries
  2. Lou Malnati's Pizzeriain 3 itineraries
  3. Millennium Parkin 3 itineraries
  4. The Purple Pig Restaurantin 3 itineraries
  5. Griffin Museum of Science and Industryin 2 itineraries
  6. Portillo's & Barnelli's Chicagoin 2 itineraries