Night Tours · This Weekend

(9 activities)
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    Devil & the White City Tour

    (37)
    Are serial killers sorta your thing? Well, first thing, you probably shouldn't say that too loudly (except when on this tour, of course). Second, get ready for an exciting tour chronicling the life and setting of chilling serial killer H.H. Holmes and his infamous murder-spree. See the site where his famous "Murder Castle" -- a 3-story building constructed by Holmes that included a maze of over 100 windowless rooms, brick walls, stairs that lead to nowhere, and other labyrinthine constructs for his ravenous preying on victims-- once stood. Also explore the site of the 1893 World Fair integral to some of Holmes' most famous murders, all the while hearing ghost stories and learning about the history of this curious, murderous figure.
    Devil & the White City Tour

    600 N Clark St, Chicago

    • Enjoy a tour through the history, mystery, and hauntings of H.H. Holmes
    • Explore the sites of H.H. Holmes' famous murders while learning the history of this frightening figure
    • See remnants of the 1893 World Fair and the "Murder Castle" where Holmes tortured his victims
    • Thrill yourself with spooky tales and ghost stories
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    36 positive reviews
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    Haunted History Tour

    (37)
    Boo! Scared? No? Oh. How about a ghost tour? But, wait, this isn't just another run-of-the-mill ghost tour your family dragged you through. Explore the exciting thrills that mix ghosts with gangsters, and more! It's like Mario Puzo meets Ghostbusters, but in Chicago! Experience the strangeness and haunted history first-hand on a tour that does so much more than just drive past spooky places. See them up close and personal for an experience in the Windy City guaranteed to send chills up your spine. Scared now? You should be.
    Haunted History Tour

    600 N Clark St, Chicago

    • See some of the scariest and spookiest sites in Chicago with a tour that gets up close and personal
    • Learn the history and background that make these locations so seductively sinister
    • Take a ghost tour that has access to unique places and all-around strangeness
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    36 positive reviews
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    Downtown Chicago Night Helicopter Tour

    Most tours are on a bus, Segway, or your own two feet. This tour takes you a little higher. On this 45-minute helicopter ride, you'll fly over Downtown Chicago and experience the Loop in a way you'll never forget. Soaring over the city, you will see Willis Tower (formerly Sears Tower), John Hancock Building, Navy Pier, and get up close and personal with the Chicago River. You'll rise above the cityscape and experience Chicago's art, architecture, and all-around ambiance from the skies. It can only be described as breathtaking and unforgettable.
    Downtown Chicago Night Helicopter Tour

    Schaumburg Regional Airport, Schaumburg

    • Soar over Chicago in a helicopter and enjoy breathtaking bird's-eye views of the city
    • Discover the art and architecture of this historic city, like you've never before seen them
    • See famous sites, like Willis Tower, Millennium Park, Navy Pier and Chicago River
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    Haunted Chicago Segway Tour

    (19)
    Steeped in violence, mafia-related crimes, and deadly fires that claimed hundreds of thousands of lives, Chicago's a city filled with haunts. On this tour, you'll glide around the streets of Chicago on a Segway, stopping at places like the Michigan Avenue hotel, allegedly the most haunted hotel in the city, and Death Alley, where victims of the terrible Iroquois Theater fire were found. At these eerie locales, hear stories about the creepy things that've happened like unexplainable deaths and self-playing pianos. Pass the site of the Iroquois Theatre fire where over six-hundred Chicagoans perished in a single day. Here, you'll have fun in the creepiest of ways. Just make sure you're sleeping with one eye open at night...
    Haunted Chicago Segway Tour

    238 E Monroe St, Chicago

    • Feel chills standing at infamous haunted hot spots throughout Chicago, such as Death Alley and the former site of Fort Dearborn
    • Glide on a Segway through the city streets to creepy locales like the Michigan Avenue hotel, considered the most haunted hotel in Chicago
    • Learn the stories and tales behind the ghosts that haunt the city today
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    19 positive reviews
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    1893 World's Fair Tour with Bars and Food

    (6)
    Take a walk back in time to explore the 1893 World's Fair! You'll spend three hours delving into the history of the fair alongside a knowledgeable host and visit notable sites tied to the renowned event. Highlights include a hotel built specifically for the fair, the Auditorium Building's magnificently expansive lobby, a ride on an elevator manned by a human operator, the last standing pre-Chicago Fire building, and the Chicago Athletic Hotel, which once served as an exclusive men's club. Enjoy anecdotes, fun facts, and engage in in World's Fair history through clue-based games and visual scavenger hunts with a chance to win prizes! You'll also enjoy enough food samples to amount to a light meal, highlighted by a visit to the Berghoff Restaurant. At check-in, you will have the option of adding either a water, beer or glass of wine to the package. It's fair to say that this innovative Chicago tour is going to be a world of fun!
    1893 World's Fair Tour with Bars and Food

    520 S Michigan Ave, Chicago

    • Explore the history of the 1893 Chicago World's Fair with a knowledgeable guide
    • Hear stories and fun facts while playing clue-based games with a chance to win prizes
    • Enjoy enough food samples for a light meal and add a beer or glass of wine to the package
    • Get to know Chicago's history with an innovate and educational touring experience
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    6 positive reviews
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    By Night Mafia and Blues Tour

    First, you will visit the chilling spot where the St. Valentine's Day Massacre murders took place and talk about the events that "lead" up to it. You'll learn about prohibition and how it still happens today in a different form and see how the music of the slaves known as the Blues became a powerful tool to help grow the Mafia in Chicago. Next you will explore some of the bars and nightlife that now dominates Chicago's north-side and will make a stop at a legendary bar previously owned by Al Capone, a Chicago Landmark. There will be some time to enjoy a drink (not included) and possibly some live music in the spirit of the 1920s. This tour will then end with a short sightseeing drive to enjoy the view of Chicago's skyline at night.
    By Night Mafia and Blues Tour

    Downtown Chicago Hotels, Chicago

    • Get inside tips from a local and expert tour guide
    • The small tour group ensures personal service for you and guests
    • This private tour is operated with just your party and a guide/driver
    • See the sights illuminated at night
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    Haunted Chicago Segway Tour

    (1)
    Do you believe in ghosts? If not, you may start to after this tour. As you follow your guide through the streets of Chicago on a personal Segway, you'll travel down secluded alleys, visit hotel lobbies, and glide along the Chicago River, listening as your guide recounts terrific tales of the city's haunted past, including disasters and gangster murders. Was that just a breeze you felt on your neck? Feel goosebumps on your arms and legs as you stand in the alley where more than 600 Chicagoans perished in 1903. Listen for the faint sound of an unmanned piano playing in the ballroom of the Michigan Avenue Hotel. Stand at the shore of the Chicago River -- the sight of Chicago's most tragic maritime disaster that claimed the lives of 800 people in 1915. Watch out, you don't want to become the haunter.
    Haunted Chicago Segway Tour

    100 S Michigan Ave, Chicago

    • Traverse Chicago's haunted alleys, hotel lobbies, and waterfront on a Segway
    • Recount the tales of the city's haunted past including disasters and infamous gangster murders
    • Embrace the dark side of Chicago's history as you visit the scariest sights the city has to offer
    • Enjoy views of the city lit up at night
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    1 positive reviews
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    Night Segway Tour

    (54)
    Hop on the most innovative tour to hit Chicago in years! Gliding through the Windy City on an eco-friendly Segway is the coolest ride of the 21st century. Far easier than walking, and more unique and personalized than a coach tour, riding a Segway personal transporter is a once-in-a-lifetime experience. See all the famous Chicago sights light up for the night, such as Buckingham Fountain, Navy Pier, and Lake Michigan. You'll receive a great orientation of Chicago from the informative commentary highlighting the city's past and present. Who knew learning about your city could be this much fun!
    Night Segway Tour

    910 S Michigan Ave, Chicago

    • Glide through the Windy City on an eco-friendly Segway
    • Visit the famous Chicago sights that light up the night, such as Buckingham Fountain and Navy Pier
    • Enjoy your guide's stories and commentaries that highlight the city's past and present
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    54 positive reviews
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    Glide at Night Segway Tour

    (5)
    Maybe the lights from the gorgeous skyline aren't enough for you. How do fireworks sound? Here's your opportunity to see both! This tour highlights the Navy Pier fireworks display as well as allows you to enjoy the subtle Chicago skyline at dusk. View the festive background of lights from the Buckingham Fountain as the breeze and mist sweep past you. As Lake Michigan glistens with dazzling fireworks, experience the picturesque city of Chicago like you've never seen before--and watch it come alive!
    Glide at Night Segway Tour

    505 N Lake Shore Dr, Chicago

    • Watch fireworks light up the sky from Chicago's Navy Pier
    • Take in picturesque sights as you explore the pier and its surrounding areas by Segway
    • Enjoy the cool breeze and festive atmosphere on this unique tour
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    5 positive reviews

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