5. Host Your Own Yacht Party
Cruise Lake Michigan with your very own margarita bar (or full premium bar), nibbling on beef tenderloin sliders while your private mixologist fixes you an Old Fashioned. From Navy Pier to North Avenue Beach, you'll see the city from a new angle, the way it was always meant to be seen.
$275 an hour and up. Sun Sea Yacht Charter at Burnham Harbor, 1559 S. Lake Shore Drive, South Loop. (708-482-4709).