Tours in Illinois

Up to 33% Off a Sailing Tour on Tall Ship Windy

Tall Ship Adventures of Chicago

Navy Pier

$30 $20

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 75 minutes

Up to 56% Off Pizza Walking Tour

Slice of Chicago Pizza Tours

Near North Side

$90 $42

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2-hour, 1.2-mile walking tour hits Pizzeria Uno, Pizzeria Ora, and Giordano's in River North to sample deep-dish pizza and learn its history

Up to 55% Off Chicago Architecture Walking Tour

Inside Chicago Walking Tours

On Location

$20 $10

A former teacher and improv comedian offers a slice of Chicago architecture during engaging walking tour

Tour Chicago's Moving Bridges with a Civil Engineer

Moving-Bridge Tour

The Loop

$20 $20

Retired Civil Engineer Jim Phillips expands on the how and why of Chicago's moving bridges during a tour by foot and water taxi

Up to 60% Off an Italian Food Tour of Chicago

Great Food Tours

Chicago

$50 $25

Sample Chicago-style pizza, italian beef, and artisan products during a two-hour Italian-food tour along the Magnificent Mile

Up to 43% Off from Segway Experience of Chicago

Segway Experience of Chicago

The Loop

$65 $37

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Atop a latest-generation Segway PT, guests coast past Buckingham Fountain and Millennium Park, occasionally pausing for photo ops

Up to 50% Off Chicago History Tour

Chicago's Finest River Walk Tour

The Loop

$40 $20

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Pedway's heated tunnels and sky bridges ferry guests between landmarks; tragedies tour examines Great Chicago Fire among other events

Half Off a Haunted-History Walking Tour

Spirit Expeditions

$50 $25

A two-hour walking tour covers most haunted areas and allows guests to conduct their own paranormal investigation

Up to 78% Off from TikiBoat Chicago

TikiBoat Chicago

Monroe Harbor

$1,799 $399

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36-foot party barge with water slide ferries guests onto Lake Michigan and Chicago River; amenities include stereo, grill, and full bathroom

Up to 61% Off Urban Scavenger Hunt

CityScape Adventures

Cubby Bear

$100 $40

Five-hour scavenger hunt takes participants through 12 challenges that encourage them to explore the city while testing their mettle

Up to 38% Off from Weird Chicago Tours

Weird Chicago Tours

Near North Side

$60 $39

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Travel by bus to the former crime scenes, red-light districts, gangster hangouts, or ghost-sighting spots of Chicago's storied past

Up to 51% Off an After-Work Cruise

ChicagoCruiseTickets.com

Chicago

$25 $13

Cruises aboard a yacht with dance floors and bars provide brilliant evening views of the Chicago skyline

Up to 53% Off from Chicago Crime Tours

Chicago Crime Tours

Chicago

$79.90 $38

Learn about more than 100 years of Chicago’s crime history in a 90-minute tour of famous crime scenes and landmarks

Up to 55% Off Arcade Tournament League

BUCKit List Events

Multiple Locations

$80 $39

Three-person teams go head-to-head in seven-week arcade tournament with one week of playoffs

Up to 55% Off Arcade Tournament League

BUCKit List Events

Multiple Locations

$80 $39

Three-person teams go head-to-head in seven-week arcade tournament with one week of playoffs

Up to 57% Off Social Game Experience

Waxwing Puzzle Co.

Logan Square

$40 $20

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Players take part in a role-playing event that is set in the prohibition era and pulls from mob folklore

50% Off Deluxe Wine Tour for Two or Four

Windy City Wine Tours

Near North Side

$800 $398

Groups up to 10 tour midwest wineries while learning the history and bakground of each vineyard and its wine

Up to 52% Off Chicago Sports Tour

Chicago Sports Tours

Chicago

$42 $21

Saturday sports tours explore Chicago's rich history of football, baseball, basketball, and hockey

Up to 52% Off True Crime and City Highlights Tour Bundle

Chicago Prime Tours

Chicago

$66 $34

Hear the stories of John Dillinger, John Wayne Gacy. and H.H. Holmes during crime tour, and visit Willis Tower and other sites on city tour

Select Local Merchants

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.

600 North Clark Street
Chicago,
IL
US

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.

43 East Jefferson Avenue
Naperville,
IL
US

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.

110 E Third St
Alton,
IL
US

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.

1940 George Street
Melrose Park,
IL
US

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.

435 Confluence Tower Drive
Hartford,
IL
US

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.

4870 N Paulina St
Chicago,
IL
US

Illinois Scene