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.
On tours from Haunted Hometowns, each traveler clutches an EMF meter, nervously waiting for a flash that detects electromagnetic fields, thus signaling the presence of paranormal activity. Meanwhile, a seasoned storyteller imparts gripping tales of murder, local legends, and ghostly encounters. Based on the books of ghost historian and storyteller Diane Ladley, Haunted Hometowns tours build on her four decades of research, as well as her intimate knowledge of the area and its rumored spectral inhabitants. Guides encourage participants to tote along their cameras so that they’re prepared to preserve the spooky sights along the way and catch photo-bombing ghosts in the act.
Legend has it that Mark Twain once called Alton a "dismal little river town," perhaps referencing the area's propensity for disease, disaster, and Civil War–era violence—some of which radiated from a Confederate POW camp. Roughly a century later, another author, Troy Taylor, wrote an entire book about Alton's dark history. He also created Alton Hauntings, a company that hosts walking and bus tours that explore malevolent stories from Alton's past, as well as the supernatural happenings that have been rumored for decades. Guides lead groups to various locations throughout the town, summoning the past through their storytelling.
After undergoing a complete overhaul for the 2013 season, Eleventh Hour Haunted House swallows visitors in 30,000 square feet of strobe lights, fog, and theme park-quality sets—some of which loom over patrons at 20 feet high. Such epic scale has earned the indoor labyrinth a coffin full of accolades, including the title of "Best Overall Halloween Event" from ChicagoHalloweenGuide.com last year. But despite the ominous environments and bloodcurdling characters, Eleventh Hour actually eliminates the scariest part of the season: long waits. Instead of making guests stand in line or rake invisible leaves before heading inside, the haunted house invites them to kill time in a festival area with food and refreshments for sale.
In December 1803, Captains Meriwether Lewis and William Clark set up the Camp River Dubois, right where the Mississippi and Missouri rivers meet. There, they and a crew of 30 men spent five months preparing for their legendary three-year expedition to chart America's newly acquired Louisiana Purchase territory. On May 14, 1804, they finally set sail on a 55-foot-long keelboat, named for its habit of keeling over in fear when it passed a shark.
To commemorate the bicentennial of its namesake's journey, the Lewis & Clark Confluence Tower opened on May 14, 2010, the 206-year anniversary, to the day, of the expedition's embarking. Tower is a slight misnomer—the structure is actually two parallel towers, connected by viewing levels 50, 100, and 150 feet above the ground.
The platforms afford panoramic views of Lewis and Clark's departure point, as well as the rivers' intersection, and, 25 miles north, the union of the Mississippi and Illinois rivers. Downtown St. Louis and the Gateway Arch are visible on clear days, and during evening events, sunsets and fireworks reflect gorgeously on the water. Back on the ground, the Meeting of the Great Rivers National Scenic Byway, complete with educational plaques, accommodates visitors interested in following the rivers' convergence on foot.
Chicago Elevated, run by effusive improv veteran Margaret Hicks, leads curious charges on eclectic group, private, and custom tours of the city. Jaunts lead natives and tourists alike through the city’s oft-overlooked nooks and crannies as Hicks’s jovial voice narrates every step, shedding light on secret areas and easily overlooked historic sites. Her pedway tour sojourns into Chicago’s tiled subterranean antecity, where retailers, restaurants, and mole people mingle. Tours explore sites of famous disasters, visit the ghostly red-light district that once stretched below what is now Printer’s Row, and gaze at downtown’s ornate architecture from the riverwalk.
Stationed in Wrigleyville after college, Hicks accrued the healthy sense of humor and comedic timing that pepper each tour at Second City, iO, and other theaters. Though she attempted a move to New York City, Hicks soon discovered she couldn’t stay away from Chicago’s majestic skyline or the skyscrapers’ subtly receding hairlines. A stint in the Chicago Architecture Foundation’s docent program, as well as acting as a tour guide for six years, arm her with insider’s knowledge that soon transfers to listeners’ brains.