Look closely northeast of the Lincoln Park Conservatory – at the corner of Fullerton and Cannon Drs – and you’ll spy the Caldwell Lily Pool, an enchanted, hidden garden. Famed landscape architect Jens Jenson designed it in 1938 using the Prairie style, native plants, and stonework that resembles the stratified canyons of the Wisconsin Dells. Today the natural area is...

The Victorian-era glass conservatory is great for a walkabout through jungles ferns, desert palms, and tropical orchids. The little hothouse only takes 30 minutes to wander through. It’s especially welcome in winter, when it remains a sultry, 75-degree escape from the icy winds raging outside.  

Millennium Park is a jackpot of free and arty sights. Start with a visit to the 110-ton Bean sculpture for the ultimate Chicago photo op, move on to splashy Crown Fountain with its puckering human gargoyles, then on to the wildflower-strewn Lurie Garden to ditch the crowds. Free activities reach their peak in summer. Acoustically awesome Pritzker Pavilion hosts free...