- $149 for one tandem skydiving jump ($299 value)
Jumping out of an airplane is always more fun with company—especially if it's your first jump. Hence Skydiving Chicago-Milwaukee's tandem skydives, during which customers plunge through the air while strapped to an instructor. After a 30- to 60-second freefall, the expert deftly deploys the parachute, initiating a lazy canopy ride lasting up to nine minutes. Visitors can also learn to dive alone—and execute cool aerial flips—in the company's seven-level skydiving school.