Explore trips
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
Itinerary map
Trip calendarFollow the locations in itinerary order. Longer itineraries open in consecutive Google Maps sections.
- 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
- Open route section 2 in Google Maps Chicago Loop, Chicago Chicago Chicago Loop, Chicago The Rookery Building, Chicago Chicago Riverwalk, Chicago
- Open route section 3 in Google Maps Chicago Riverwalk, Chicago DuSable Bridge, Chicago Chicago River, Chicago Chicago Riverwalk, Chicago River North, Chicago
- Open route section 4 in Google Maps River North, Chicago Chicago Chicago Loop, Chicago Bronzeville, Chicago Bronzeville Walk of Fame, Chicago
- Open route section 5 in Google Maps Bronzeville Walk of Fame, Chicago Bronzeville, Chicago South Michigan Avenue, Chicago Chicago Loop, Chicago Chicago, Illinois
- Open route section 6 in Google Maps Chicago, Illinois Chicago Chicago Loop, Chicago Griffin Museum of Science and Industry, Chicago Hyde Park, Chicago
- Open route section 7 in Google Maps Hyde Park, Chicago University of Chicago, Chicago Chicago Loop, Chicago Chicago Chicago Loop, Chicago
- Open route section 8 in Google Maps Chicago Loop, Chicago Chicago Cultural Center, Chicago Daley Plaza, Chicago Chicago Loop, Chicago Chicago Riverwalk, Chicago
- Open route section 9 in Google Maps Chicago Riverwalk, Chicago Chicago Loop, Chicago Chicago Millennium Park, Chicago Art Institute of Chicago, Chicago
- 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
- Open route section 11 in Google Maps South Loop, Chicago Chicago West Loop, Chicago Chicago French Market, Chicago Greektown, Chicago
- Open route section 12 in Google Maps Greektown, Chicago Fulton Market District, Chicago West Randolph Street, Chicago West Loop, Chicago Chicago
- Open route section 13 in Google Maps Chicago Chicago Loop, Chicago Daley Plaza, Chicago Staypineapple, An Iconic Hotel, The Loop, Chicago
Stops in order
- Chicago Day 1
- Staypineapple, An Iconic Hotel, The Loop, Chicago Day 1
- Chicago Riverwalk, Chicago Day 1
- Chicago Cultural Center, Chicago Day 1
- Chicago Loop, Chicago Day 1
- Chicago Day 2
- Chicago Loop, Chicago Day 2
- The Rookery Building, Chicago Day 2
- Chicago Riverwalk, Chicago Day 2
- DuSable Bridge, Chicago Day 2
- Chicago River, Chicago Day 2
- Chicago Riverwalk, Chicago Day 2
- River North, Chicago Day 2
- Chicago Day 3
- Chicago Loop, Chicago Day 3
- Bronzeville, Chicago Day 3
- Bronzeville Walk of Fame, Chicago Day 3
- Bronzeville, Chicago Day 3
- South Michigan Avenue, Chicago Day 3
- Chicago Loop, Chicago Day 3
- Chicago, Illinois Day 3
- Chicago Day 4
- Chicago Loop, Chicago Day 4
- Griffin Museum of Science and Industry, Chicago Day 4
- Hyde Park, Chicago Day 4
- University of Chicago, Chicago Day 4
- Chicago Loop, Chicago Day 4
- Chicago Day 5
- Chicago Loop, Chicago Day 5
- Chicago Cultural Center, Chicago Day 5
- Daley Plaza, Chicago Day 5
- Chicago Loop, Chicago Day 5
- Chicago Riverwalk, Chicago Day 5
- Chicago Loop, Chicago Day 5
- Chicago Day 6
- Millennium Park, Chicago Day 6
- Art Institute of Chicago, Chicago Day 6
- South Michigan Avenue, Chicago Day 6
- Grant Park, Chicago Day 6
- Monroe Harbor, Chicago Day 6
- South Loop, Chicago Day 6
- Chicago Day 7
- West Loop, Chicago Day 7
- Chicago French Market, Chicago Day 7
- Greektown, Chicago Day 7
- Fulton Market District, Chicago Day 7
- West Randolph Street, Chicago Day 7
- West Loop, Chicago Day 7
- Chicago Day 8
- Chicago Loop, Chicago Day 8
- Daley Plaza, Chicago Day 8
- 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.