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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1914
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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* A traveler said: "Lizzie was very informative, fun, and personable. I enjoyed hearing stories about Chicago I’d never heard before and seeing the fabulous Palmer Hotel."


Windy City Ghost Tour

Windy City Ghost Tour

star-4
23
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$24.09
From
$24.09
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.
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* A traveler said: "The tour was very informative. Rachel was great. Should be a stop for anyone who likes to hear some creepy ghost stories."


Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6405
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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* A traveler said: "Great tour with outstanding guide who made the experience memorable with interesting stories and facts."


Big Bus Chicago Night Tour

Big Bus Chicago Night Tour

star-4
64
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$29.00
From
$29.00
See Chicago's dazzling skyscrapers lit up for the night during this 75-minute Big Bus tour. The entire loop takes passengers from Navy Pier, down the Magnificent Mile to Michigan Avenue, through the Museum Campus and around the architectural gems on the Loop skyline. Live and audio commentary available in English.
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* A traveler said: "Awesome tour! Our guide was funny and informative. We saw great sites! We stopped on Museum Campus for a night time city sky line photo opt. It was the best thing we did while in Chicago! Highly recommend!"


90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1116
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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* A traveler said: "Awesome experience! Our host was funny, knowledgeable and very personable. He certainly knows his Chicago history!"


Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1037
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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* A traveler said: "The history learned was really cool. Tour guide Mike was very knowledgeable and fun. My kids enjoyed as well"


Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
483
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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* A traveler said: "Great tour, great knowledge and great views! Enjoyed the bar down stairs and AC as a. Option to stay outside the sun"


Chicago Night Crimes Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Night Crimes Bus Tour

star-4.5
98
  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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* A traveler said: "Katie was very informative and entertaining. Enjoyed seeing the neighborhoods we went through and many restaurants."


Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
250
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$65.99
From
$65.99
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
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* A traveler said: "Our tour guide, Brooke, was fabulous! She was very knowledgeable and entertaining. I would definitely recommend this day tour. Lots of fun and lots of food!!"


45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
127
  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$23.00
From
$23.00
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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* A traveler said: "Did the night time tour. It was stunning. Cool history on the buildings too. 1/2 way through you get the most beautiful and breathtaking view of the skyline all lit up In the night."


Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
865
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$26.10
From
$26.10
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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* A traveler said: "All of it. Ricardo was engaging and provided helpful tidbits. The ride was comfortable and safe. I would do it again."


Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
303
  • 40 minutes
  • Free Cancellation
  • Taking safety measures
From
$27.25
From
$27.25
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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* A traveler said: "Really nice. Just the right amount of time for this cruise. It was clean and the staff was friendly."


Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
From
$26.67
Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.
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* A traveler said: "We loved getting to know the city and seeing Amazing art where you least expected it. The itour guide was excellent."


2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
27
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
More

* A traveler said: "We absolutely loved our Haunted Segway Tour! Our guide, Carrie was really hilarious and made our tour truly memorable. Segway is definitely the best way to see the large variety of interesting sights throughout the city! Such a blast! Highly recommend!!"


Haunted Chicago Ghost and Pub Walking Tour
Likely to Sell OutLikely to Sell Out

Haunted Chicago Ghost and Pub Walking Tour

star-4.5
10
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$31.50
From
$31.50
Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
More

2-Hour Haunted History Chicago Night Tour

2-Hour Haunted History Chicago Night Tour

star-5
4
  • 2 hours
  • Taking safety measures
From
$29.00
From
$29.00
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.
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* A traveler said: "Our guide was fantastic! He was friendly and knowledgeable, and carried on in the face of thunder and lightning (which was perfect). Great value for money!"


West Town Instagram Hot Spots Tour By Native 312

West Town Instagram Hot Spots Tour By Native 312

star-4
4
  • 1 hour 30 minutes to 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$25.00
From
$25.00
Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene.
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Original Chicago Haunting Ghost Bus Tour

Original Chicago Haunting Ghost Bus Tour

star-4.5
4
  • 2 hours 30 minutes to 3 hours
  • Taking safety measures
From
$49.00
From
$49.00
Our classic Chicago Hauntings Chicago Ghost tour is a 2.5 to 3-hour fully-narrated tour by coach bus, with numerous stops along the tour route at some of the most actively haunted sites in Chicago, including the site of the Eastland Disaster, where 844 souls perished on the Chicago River; Death Alley, where more than six hundred children and their chaperones lost their lives in the worst single building fire in American history; the site of the infamous St. Valentine’s Day Massacre in storied Lincoln Park, the original and the now abandoned City Cemetery, where an estimated 13,000 unmarked graves remain. Some of our most common stops include murder sites, disaster sites, cursed skyscrapers, gangland sites, Chicago’s most haunted house, and others. You are welcome to take photos at all of our stops — sometimes your camera may capture more than just spooky scenery.
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Chicago Haunted Halloween Segway Tour

Chicago Haunted Halloween Segway Tour

star-4.5
4
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58
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!
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Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
3
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
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* A traveler said: "Steve was a great guide. He allowed us to make the tour our own and went off the path to show us cool things based on our questions. We learned things about the early gangsters and some things about Chicago, it's buildings and neighborhoods. We wouldn't have seen or known these things if we were left to explore on our own in the few days we had here. He took pictures of our group for us and showed us some great spots for photos.. Overall very informative and casual. Our driver was great as well. Courteous and a gentleman who kept us safe in the traffic."


Lincoln Park Hauntings Chicago Ghost Tour and Ghost Hunt

Lincoln Park Hauntings Chicago Ghost Tour and Ghost Hunt

star-5
3
  • 2 hours 30 minutes
  • Taking safety measures
From
$29.00
From
$29.00
The only Chicago ghost tour where YOU are the ghost hunter! Join our guide for a chilling walk through the legendary Lincoln Park, site of the original City Cemetery and the St. Valentine’s Day Massacre.
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* A traveler said: "Definitely educational and we learned a lot about the area, as well as the ghosts there. History, folklore and real accounts are all told. Ghost equipment used is OK, nothing too spectacular but we honestly really enjoyed ourselves and Tony was a great and engaging guide."


Fright Hike: Chicago Halloween Bike Tour

Fright Hike: Chicago Halloween Bike Tour

star-5
2
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
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Private Haunted History of Chicago Ghost Tour

Private Haunted History of Chicago Ghost Tour

star-5
1
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Discover spooky stories in the Windy City on a private haunted history tour. Visit places with names such as the Murder Castle and Death Alley, and hear about Al Capone and the Old Congress Hotel. See all three locations on one tour that reveals fascinating details about historical events, and rumors of murder and mayhem in Chicago.
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Pilsen Walking Tour of Local Publicly Displayed Art

Pilsen Walking Tour of Local Publicly Displayed Art

  • 1 to 2 hours
  • Free Cancellation
From
$15.00
From
$15.00
We find quality art from around the city by local artists that have significance towards local artists. Unique opportunity to appreciate homegrown art from local Chicagoans and to receive artistic inspiration.
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