Take in the skyline from Promontory Point
Enjoy an incredible view of the city from the Alfred Caldwell-designed Promontory Point in Burnham Park. The south lakefront park also has beaches and bird sanctuaries to explore.
Hit up The 606 (and easily see four different neighborhoods)
Bucktown/Wicker Park/Logan Square/Humboldt Park
What was once an abandoned section of rail line is now one of the city's best recreational paths for scouting out four different neighborhoods. The 606 (or Bloomingdale Trail) stretches 2.7 miles through Bucktown, Wicker Park, Logan Square, AND Humboldt Park. Pick a spot to eat/drink along the way.
Take the picnic to the stage
Expertly curated (and free!) performances and film showings at the Jay Pritzker Pavilion in Millennium Park regularly draw city-goers to The Loop during Chicago's warmer months. So it stands to reason that THE thing to do with those visiting "in season" would be to grab a blanket, bottle of wine, and some snacks, and hit the grass near the stage with all the other city dwellers.