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North America · Single base · 7 NIGHTS

Chicago slow stay · Blues history and live music candidate

Spend time on a secondary interest and protect a low-pressure day

Use this itinerary

Itinerary map

Trip calendar

Follow the locations in itinerary order. Longer itineraries open in consecutive Google Maps sections.

  1. Open route section 1 in Google Maps Chicago Staypineapple, An Iconic Hotel, The Loop, Chicago Chicago Riverwalk, Chicago Chicago Cultural Center, Chicago Chicago Loop, Chicago
  2. Open route section 2 in Google Maps Chicago Loop, Chicago Chicago Chicago Loop, Chicago The Rookery Building, Chicago Chicago Riverwalk, Chicago
  3. Open route section 3 in Google Maps Chicago Riverwalk, Chicago DuSable Bridge, Chicago Chicago River, Chicago Chicago Riverwalk, Chicago River North, Chicago
  4. Open route section 4 in Google Maps River North, Chicago Chicago Chicago Loop, Chicago Bronzeville, Chicago Bronzeville Walk of Fame, Chicago
  5. Open route section 5 in Google Maps Bronzeville Walk of Fame, Chicago Bronzeville, Chicago South Michigan Avenue, Chicago Chicago Loop, Chicago Chicago, Illinois
  6. Open route section 6 in Google Maps Chicago, Illinois Chicago Chicago Loop, Chicago Griffin Museum of Science and Industry, Chicago Hyde Park, Chicago
  7. Open route section 7 in Google Maps Hyde Park, Chicago University of Chicago, Chicago Chicago Loop, Chicago Chicago Chicago Loop, Chicago
  8. Open route section 8 in Google Maps Chicago Loop, Chicago Chicago Cultural Center, Chicago Daley Plaza, Chicago Chicago Loop, Chicago Chicago Riverwalk, Chicago
  9. Open route section 9 in Google Maps Chicago Riverwalk, Chicago Chicago Loop, Chicago Chicago Millennium Park, Chicago Art Institute of Chicago, Chicago
  10. Open route section 10 in Google Maps Art Institute of Chicago, Chicago South Michigan Avenue, Chicago Grant Park, Chicago Monroe Harbor, Chicago South Loop, Chicago
  11. Open route section 11 in Google Maps South Loop, Chicago Chicago West Loop, Chicago Chicago French Market, Chicago Greektown, Chicago
  12. Open route section 12 in Google Maps Greektown, Chicago Fulton Market District, Chicago West Randolph Street, Chicago West Loop, Chicago Chicago
  13. Open route section 13 in Google Maps Chicago Chicago Loop, Chicago Daley Plaza, Chicago Staypineapple, An Iconic Hotel, The Loop, Chicago

Stops in order

  1. Chicago Day 1
  2. Staypineapple, An Iconic Hotel, The Loop, Chicago Day 1
  3. Chicago Riverwalk, Chicago Day 1
  4. Chicago Cultural Center, Chicago Day 1
  5. Chicago Loop, Chicago Day 1
  6. Chicago Day 2
  7. Chicago Loop, Chicago Day 2
  8. The Rookery Building, Chicago Day 2
  9. Chicago Riverwalk, Chicago Day 2
  10. DuSable Bridge, Chicago Day 2
  11. Chicago River, Chicago Day 2
  12. Chicago Riverwalk, Chicago Day 2
  13. River North, Chicago Day 2
  14. Chicago Day 3
  15. Chicago Loop, Chicago Day 3
  16. Bronzeville, Chicago Day 3
  17. Bronzeville Walk of Fame, Chicago Day 3
  18. Bronzeville, Chicago Day 3
  19. South Michigan Avenue, Chicago Day 3
  20. Chicago Loop, Chicago Day 3
  21. Chicago, Illinois Day 3
  22. Chicago Day 4
  23. Chicago Loop, Chicago Day 4
  24. Griffin Museum of Science and Industry, Chicago Day 4
  25. Hyde Park, Chicago Day 4
  26. University of Chicago, Chicago Day 4
  27. Chicago Loop, Chicago Day 4
  28. Chicago Day 5
  29. Chicago Loop, Chicago Day 5
  30. Chicago Cultural Center, Chicago Day 5
  31. Daley Plaza, Chicago Day 5
  32. Chicago Loop, Chicago Day 5
  33. Chicago Riverwalk, Chicago Day 5
  34. Chicago Loop, Chicago Day 5
  35. Chicago Day 6
  36. Millennium Park, Chicago Day 6
  37. Art Institute of Chicago, Chicago Day 6
  38. South Michigan Avenue, Chicago Day 6
  39. Grant Park, Chicago Day 6
  40. Monroe Harbor, Chicago Day 6
  41. South Loop, Chicago Day 6
  42. Chicago Day 7
  43. West Loop, Chicago Day 7
  44. Chicago French Market, Chicago Day 7
  45. Greektown, Chicago Day 7
  46. Fulton Market District, Chicago Day 7
  47. West Randolph Street, Chicago Day 7
  48. West Loop, Chicago Day 7
  49. Chicago Day 8
  50. Chicago Loop, Chicago Day 8
  51. Daley Plaza, Chicago Day 8
  52. Staypineapple, An Iconic Hotel, The Loop, Chicago Day 8

To see every stop on one map, import the CSV in Google My Maps and select Place as the location column.