Tours in Chicago

Tour by Bus for Two or Four from Chicago Crime Tours (Up to 53% Off)

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

Walking Tour from WendyCity (Up to 51% Off). Two Options Available.

WendyCity

Multiple Locations

$50 $25

Tour the Mag Mile and learn some of its history during a relaxed walk before the stores open

Chocolate Tour of Chicago with Seven Tastings for One, Two, or Four from Great Food Tours (Up to 67% Off)

Great Food Tours

Chicago

$50 $20

Sample Aztec chocolate drinks, cupcakes, truffles, and chocolate donuts during two-hour chocolate tour along the Magnificent Mile

Sightseeing Tours for Two from Chicago's Finest Tours (Up to 52% Off)

Chicago's Finest Tours

Multiple Locations

$60 $29

(323)

Tours take guests along Chicago's historic River Walk, into jazz clubs, or to a hearty brunch buffet

Discover the Kinetic Art of Chicago's Moving Bridges

Moving-Bridge Walking Tour

Chicago

$15 $15

Walk the streets of the Loop with civil engineer Jim Phillips and watch the Chicago River's movable bridges in action

Deep-Dish-Pizza Walking Tour for Two or Four from Slice of Chicago Pizza Tours (Up to 56% Off)

Slice of Chicago Pizza Tours

Near North Side

$90 $42

(13)

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

Chicago Architecture Walking Tour for 1 or 2 Youths or Adults from Inside Chicago Walking Tours (Up to 55% Off)

Inside Chicago Walking Tours

On Location

$20 $10

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

"Speakeasy" Social Game Experience for One, Two, Four, or Eight at Waxwing Puzzle Co. (Up to 65% Off)

Waxwing Puzzle Co.

Lincoln Square

$40 $16

(62)

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

Haunted-History Walking Tour for Two or Four with Ghost-Hunting Equipment from Spirit Expeditions (50% Off)

Spirit Expeditions

South Loop

$50 $25

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

Running Tours of Downtown Chicago from Chicago Running Tours & More (Up to 55% Off)

Chicago Running Tours & More

Central Chicago

$32 $15

Professional guides lead sightseeing tours at a jogging pace during excursions that emphasize fun and learning over speed

Admission for One or Two to Chicago Sports Tours (Up to 52% Off)

Chicago Sports Tours

Chicago

$42 $21

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

True Crime and City Highlights Tour Bundle for One, Two, or Four from Chicago Prime Tours (Up to 61% Off)

Chicago Prime Tours

Chicago

$66 $27

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

$25 for Entry to Chicago Challenge: The Ultimate Urban Scavenger Race on Saturday, July 12 ($55 Value)

The Ultimate Urban Scavenger Race

Lizzie McNeills Irish Pub

$55 $25

Teams race to solve clues and strategize to win cash prizes and awards during urban race; music and drink specials at post-race party

Loop Interior Architecture Walking Tour for Two or Four from Chicago Detours (Up to 47% Off )

Chicago Detours

Chase Tower

$52 $29

(155)

Featured in the Chicago Reader, guides lead groups through architecturally striking interiors and share photos and videos via iPads

Entry for One or Team of Four to the Ultimate Barcrawl Challenge (Up to 50% Off)

Ultimate Barcrawl Challenge

Deuce's

$15 $8

Goldfish races, relay races, and other drinking games are held at four Wrigleyville bars

$37 for a Two-Hour Segway Tour of Downtown Chicago from Segway Experience of Chicago (Up to $65 Value)

Segway Experience of Chicago

The Loop

$65 $37

(43)

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

Downtown Foodie Walking Tour for One, Two, or Four from Food Tank (Up to 70% Off)

Food Tank

Art Institute

$65 $25

Explore downtown Chicago's food scene and local landmarks on a walking tour that starts at Millennium Park and ends at the Field Museum

Sunset Segway Tour from Millennium Park or Hyde Park Tour for Two from Bike and Roll Chicago (50% Off)

Bike and Roll Chicago

Multiple Locations

$138 $69

(270)

Segways effortlessly glide through the city streets, allowing riders to breeze by Frank Lloyd Wright's Robie House or Soldier Field

Three-Hour Historical Bus Tour for Two or Four from Weird Chicago Tours (Up to 38% Off)

Weird Chicago Tours

Near North Side

$60 $39

(96)

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

Select Local Merchants

The bronze likeness of Michael Jordan—the Bulls' #23 and basketball's undisputed king—leaps into the air in front of the United Center, ascending into the annals of sports history. Across town, the sound of Babe Ruth's most famous homer rebounds off of the iconic walls of Wrigley Field. The Roman-meets-modern architecture of Soldier Field—where Walter Payton, Mike Ditka, and "The Fridge" grew to larger-than-life—straddles Chicago's lakefront. The resounding Black Sox scandal clashes with the victorious 2005 World Series Champs banners at U.S. Cellular Field, where the White Sox's famous exploding scoreboard towers above the Bridgeport neighborhood.

During an air-conditioned bus ride, local comedians wax historic as tourists are brought within earshot and camera-shot of Chicago's proudest pro-sports franchises. The Chicago Sports Tour parades from the North to the South side, brushing shoulders with famous ballparks and weaving through more than a century of athletic anecdotes and civic pride. Augmented by laughs and entertainment, it reveals more than the brick-and-mortar façades of the famous stadiums. The guides bring each building to life with fascinating anecdotes, and rides from one stadium to the next cover neighborhoods such as Wrigleyville, Bridgeport, and Little Italy—where fans and players alike eat, drink, and argue about their favorite peanut vendors.:m]]

430 North Michigan Avenue
Chicago,
IL
US

In the middle of a tour, a young woman began arguing with her mother, causing the guide to quietly usher the rest of the group away from the quarreling family members. Even if they had stayed, the other tour participants would have only heard half the dispute. That's because the mother was dead. At Chicago Ghost Investigations, instances like these in which guests are confronted by spirits of their past are jokingly referred to as Bring Your Own Ghost moments. Owner Brian is all too familiar with these types of encounters, experiencing one himself while serving with the US Army's 101st Airborne Division. While shivering in a foxhole, Brian suddenly found himself looking down at his body from above. Beside him stood his deceased grandfather, donning a tuxedo and red bow tie.

Brian has been fascinated with ghosts ever since, sharing his passion during each paranormal encounter at Chicago Ghost Investigations. During an introductory session, he supplies guests with a bag of ghost hunting equipment, including divination rods, thermal indicators. Along with these tools, Brian and his fellow guides teach participants methods for communicating with the dead. From there, newly christened ghost hunters seek out spirits inside a warehouse once used by Al Capone, which NBC New York now calls the "spookiest place in Chicago."

500 West Cermak Road
Chicago,
IL
US

Sidewalk Food Tours of Chicago introduces tourists and locals to the Windy City's thriving food scene via deep-dish pizzas, hot dogs, and ethnic cuisine. Two neighborhoods in particular brim with famous restaurants and hidden eateries: Wicker Park and River North.

On their streets, Sidewalk Food Tours of Chicago's local guides lead groups on walking explorations, pausing frequently to taste everything from cupcakes to Top Chef Masters winner Rick Bayless's Mexican cuisine. Food stands at the crossroads of each neighborhood's culture, and the guides use it as a jumping off point to discuss local history and architecture. They might spin tales of how Wicker Park was once a hotbed of European immigration or how River North accumulated a wealth that would make John D. Rockefeller's piggy bank tremble with envy.

222 West Merchandise Mart Plaza
Chicago,
IL
US

Millennium Trolley Tours offers the only way to explore Chicago like a Californian. The tour company takes customers throughout historical and popular city areas aboard San Francisco-style trolley cars that mirror the aesthetic of the city's iconic rail transports. While traveling to various Chicago hot spots, such as the Theatre District or the Hancock Building, tour guides share historical facts about the city and its landmarks. Though you can stay aboard the trolley for the entire one-hour, 45-minute tour, passengers can also hop off to explore areas of interest, and hop back on to avoid walking on the city’s numerous hot-coal sidewalks.

440 N Wabash suite 2307
Chicago,
IL
US

Specially designed to slip effortlessly under the Potomac's low bridges, the Odyssey III has been constructed with transparent walls and open decks for hosting elegant cruises that drift by some of Washington's most scenic vistas. Cruises take advantage of the yacht?s glass windows, passing by the neoclassical splendor of the Lincoln Memorial or drifting under an illuminated night sky on full-moon cruises. Lunch, dinner, and brunch outings serve guests with delectable multicourse meals. Live music accompanies evening cruises, meaning guest can hit the boat's dance floor and show off their Nobel Prize?winning dance moves before night?s end.

600 E Grand Ave.
Chicago,
IL
US

Owner Valerie Beck and her team of chocophile tour guides lead guests on walking tours of Chicago’s historical bakeries and chocolatiers, narrating the history of beloved sweets while walking an easy route through vistas of Chicago’s stunning architectural heritage. While snacking on samples of sweets, guests learn about chocolate’s storied history, the cupcake’s rise to prominence, and how to guess the flavor of filling inside Oompa Loompas by sight. Tours convene throughout Chicago’s many neighborhoods, giving guests a sneak peek into Chicago's signature confections, boutique shops, and mobile sweet-vending trucks. The chocolate or cupcake jaunts provide the perfect setting for a girls’ day out or bachelorette party, showing tour-goers the sweeter side of the city without getting caught in construction sites of shoddily built gingerbread houses.

500 North Michigan Avenue
Chicago,
IL
US

Chicago Scene