Top Chicago Pop Culture

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the St Valentine's Day massacre * Stops on-and-off the bus at famous crime sites * True Crime history * Historic video footage * Interactive live commentary * Crime quiz * Souvenir pamphlet with photos * Luxury climate-controlled bus * So much more! Some of the world’s most notorious criminals, mobsters & gangsters bamboozled their way through Chicago. Escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop on-and-off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people overlook on a daily basis. We hope you join us to experience something truly unique in Chicago.

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it. Reservations are strongly recommended.

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

Enjoy a panoramic night-time sightseeing bus tour and be dazzled by the bright lights of Chicago. See the entire skyline lit up from the Museum Campus, discover River North’s vibrant nightlife scene, and travel every inch of Michigan Ave from The Magnificent Mile to The Cultural Mile, all in one exciting loop.

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!

Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary walking tour, complete with a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef sandwich, brownies, as well as a VIP upgrade option that includes 3-samples of locally crafted beer (you can purchase this option upon arrival for $19.99/person). Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, all the while regaling you with tales from Chicago’s rich food-centric history. This tour is sure to make memories that will last a lifetime!

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of 24 Hour and 48 Hour tickets, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck.

Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. Like Ursula, all of our guides are all real investigators and true Chicagoans. We love investigating, we love Chicago history, and we would love to show you Chicago's haunted history. This is the only tour which takes you out of the downtown area and into one of the most haunted parts of Chicago: Lincoln Park, the old City Cemetery, which was ravaged by the Great Fire of 1871, leaving 10,000 graves behind. The bodies are all still here, as well as the ghosts. The tour also visits the site of the St. Valentine's Day Massacre and the site of Suicide Bridge, where more than 100 desperate souls lost their lives.

Often imitated but never matched, this 2.5-hour to 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 18 years ago by the city's ghostlorist, Ursula Bielski. Ursula and her team of veteran paranormal researchers and historians have thrilled thousands of guests with firsthand experiences of this, one of the world's most legendarily notorious cities. We take you where the other walking tours simply can't--to the many shadowed corners where the fateful tales began. From the Fort Dearborn Massacre to the St. Valentine's Day Massacre. From the Great Chicago Fire to the Eastland Disaster. From ghost ships that sail Lake Michigan to the Chicago origins of "Ghostbusters" And to the lair of the Devil Baby of Hull House.

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire. Many of the incredible homes are still standing and the spirits linger, waiting to divulge their secrets in a haunted history tour and ghost investigation in one of Chicago's most prestigious places.

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: • Al Capone • John Dillinger • The Untouchables View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre. We bring Chicago’s true crime past to life before your very eyes.

Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a segway at night. Venture through the dark with your local guide, and see alleys, hotels, and sites of some of the most gruesome disasters and murders in Chicago’s history. During your spooky adventure through the city, you’ll also see Chicago's famous landmarks lit up in glistening lights. Join in the Halloween fun all October long! Costumed guides and ghoulish tales--this haunting good-time is not to be missed!

Discover Chicago’s haunted locations by following clues and solving puzzles on your phone. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Ready for an adventure? Highlights: 1. Explore historical places in Chicago such as the Chicago History Museum, the Standing Lincoln Monument and lesser-known places. 2. Enjoy a uniquely crafted story brought to you by our talented writers. 3. Visit the Couch Tomb Mausoleum, the only surviving gravesite in Lincoln Park. 4. You will learn the 14th C history of Prague through the eyes of their greatest medieval ruler and builder, Charles IV 5. Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt.

We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian Chicago. We visit Prairie Avenue, Chicago's Victorian "Easy Street" and site of the Fort Dearborn Massacre, travel to the World's Fairgrounds and the Midway Plaisance at the University of Chicago, and make the notorious trek to the site of Holmes' "Murder Castle."

Wind & Souls uses the ghosts of Chicago’s past to recreate a city that was and is no longer. Theater fires and the Alley of Death; HH Holmes at home in his murder castle. Chicago has seen it all. From empty tombs to mass graves leaking bodies, these stories are like gusts of wind off of Lake Michigan: they leave a chill in your bones that just won’t quit.

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Chicago and hear some of its most famous and creepy haunted stories. 21+ only. A costumed guide will lead tour goers on a 2.5-hour journey, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home. You'll visit several different bars and have time to enjoy a delicious libation (at own expense) as the guide tells them about all the spooky happenings and great history of this town! *Tour route and drink stops are subject to availability.

Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow Bobby’s expert tour guides through some of the most paranormal and frightening spots in the Windy City. This 3-hour guided bicycle tour explores the uber-haunted John Hancock Center, the site of the SS Eastland Disaster (one of the deadliest shipwrecks in American history), the 200-year old ghosts of the Congress Plaza Hotel, and more! This is the perfect outdoor activity for anyone looking to explore Chicago after dark. Connect with your inner ghost hunter and sign up today!