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North America · Single base + day trip · 6 NIGHTS

Chicago with a day in Oak Park

Add a nearby city or landscape while keeping one overnight base

Submitted by The Short Crossing
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 Millennium Park, Chicago Art Institute of Chicago, Chicago South Michigan Avenue, Chicago
  5. Open route section 5 in Google Maps South Michigan Avenue, Chicago Grant Park, Chicago Monroe Harbor, Chicago South Loop, Chicago Oak Park
  6. Open route section 6 in Google Maps Oak Park Chicago Loop, Chicago, Oak Park Oak Park, Illinois Frank Lloyd Wright Home and Studio, Oak Park, Illinois Downtown Oak Park, Illinois
  7. Open route section 7 in Google Maps Downtown Oak Park, Illinois Unity Temple, Oak Park, Illinois Chicago Loop, Chicago, Oak Park Chicago West Loop, Chicago
  8. Open route section 8 in Google Maps West Loop, Chicago Chicago French Market, Chicago Greektown, Chicago Fulton Market District, Chicago West Randolph Street, Chicago
  9. Open route section 9 in Google Maps West Randolph Street, Chicago West Loop, Chicago Chicago Chicago Loop, Chicago Griffin Museum of Science and Industry, Chicago
  10. Open route section 10 in Google Maps Griffin Museum of Science and Industry, Chicago Hyde Park, Chicago University of Chicago, Chicago Chicago Loop, Chicago Chicago
  11. Open route section 11 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. Millennium Park, Chicago Day 3
  16. Art Institute of Chicago, Chicago Day 3
  17. South Michigan Avenue, Chicago Day 3
  18. Grant Park, Chicago Day 3
  19. Monroe Harbor, Chicago Day 3
  20. South Loop, Chicago Day 3
  21. Oak Park Day 4
  22. Chicago Loop, Chicago, Oak Park Day 4
  23. Oak Park, Illinois Day 4
  24. Frank Lloyd Wright Home and Studio, Oak Park, Illinois Day 4
  25. Downtown Oak Park, Illinois Day 4
  26. Unity Temple, Oak Park, Illinois Day 4
  27. Chicago Loop, Chicago, Oak Park Day 4
  28. Chicago Day 5
  29. West Loop, Chicago Day 5
  30. Chicago French Market, Chicago Day 5
  31. Greektown, Chicago Day 5
  32. Fulton Market District, Chicago Day 5
  33. West Randolph Street, Chicago Day 5
  34. West Loop, Chicago Day 5
  35. Chicago Day 6
  36. Chicago Loop, Chicago Day 6
  37. Griffin Museum of Science and Industry, Chicago Day 6
  38. Hyde Park, Chicago Day 6
  39. University of Chicago, Chicago Day 6
  40. Chicago Loop, Chicago Day 6
  41. Chicago Day 7
  42. Chicago Loop, Chicago Day 7
  43. Daley Plaza, Chicago Day 7
  44. Staypineapple, An Iconic Hotel, The Loop, Chicago Day 7

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