A city tour exposes one to new sights and sounds and provides a solid alibi when accused of shaving the dog. Be Chicago's best friend with this Groupon.
$15 for Ticket to Hop-On Hop-Off Trolley Tour ($30 Value)
For eight hours Wednesday through Sunday, classic Chicago trolleys whisk sightseers on a tour that picks up and drops off every hour at nine stops that include the Willis Tower, Art Institute of Chicago, Navy Pier, and Water Tower Place.
Gray Line Chicago
The Chicago branch of Gray Line's global sightseeing operation organizes a wide variety of tours and excursions throughout the Windy City, from architectural tours that send passengers coasting on the river and lake for sun-drenched educational cruises to shopping odysseys at Chicago Premium Outlets, where travelers can zip through more than 100 stores and restaurants after being shuttled to the retail utopia. Blues outings treat music lovers to raw licks, soul food, and real tears at celebrated concert venues such as Buddy Guy's Legends and Rosa's Lounge.
Gray Line's cherry-red trolleys transport visitors and residents alike to famous Chicago sites. Just north of the river, the vehicles idle before the Wrigley Building's sparkling white terra cotta façade, which in the 1920s stood as the first major skyscraper outside of The Loop. From there, the trolley may motor north to the John Hancock Center, where elevators to its observatory sweep guests 96 floors in 39 seconds. The trolley could also steer south to the Willis Tower, which lost its maiden name of Sears after being charmed by a passing cumulus cloud.