Night Tours · This Weekend

(8 activities)
Reset Filters
  • Book Now

    Red Light District Tour

    Welcome to the dark side! Explore the naughtier side of Chicago with a tour of the city's famous Red Light District. See the sites of the little-known locations of the famous local sex industry. Come along and examine Chicago's sexy past, the city's original Red Light Districts, adults-only toy shops, and much more. You'll be sure to enjoy this fun and scandalous historical tour.
    Red Light District Tour

    600 N Clark St, Chicago

    • Tour Chicago's famous Red Light District and learn the historical ins and outs of the city's naughtier side
    • Explore the kinky and freaky locations of a district that just simply refuses to be ignored
    • Come with an open mind and delve into the famous local sex industry's main headquarters
    • Enjoy this wildly entertaining tour of Chicago's sexy past
    BOOK NOW ← Back
    16 positive reviews
  • Book Now

    Haunted History Tour

    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
    BOOK NOW ← Back
    16 positive reviews
  • Book Now

    1893 World's Fair Tour with Bars and Food

    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
    BOOK NOW ← Back
  • Book Now

    Original Chicago Hauntings Tour

    Check out the hauntings tour that's inspired more shivers than nails on a chalk board! You'll check out the sites of famous tragedies like the Eastland disaster and the Iroquois Theater Fire, the locations of famous ghosts like Resurrection Mary, the body dump of serial killer H.H. Holmes, the house that inspired "Rosemary's Baby," and more! This is not a "spook show" or haunted house tour filled with cheap thrills and scares. Rather, it's darkly historical, sometimes deeply disturbing, and not recommended for highly sensitive children or adults. After this tour, you'll feel a whole new connection to the city -- and all its restless, roving spirits.
    Original Chicago Hauntings Tour

    600 N Clark St, Chicago

    • Let veteran paranormal researcher Ursula Bielski show you some of Chicago's most haunted locations
    • Visit the sites of massive tragedies, including the Eastland disaster, the Iroquois Theatre Fire, the Fort Dearborn Massacre, and more
    • Explore the death site of "Resurrection Mary," and the dump of legendary serial killer H.H. Holmes
    • See the infamous Hull House, the inspiration for "Rosemary's Baby"
    BOOK NOW ← Back
    1 positive reviews
  • Book Now

    1960s Nightlife in the Gold Coast

    The 60s in Chicago -- what a time to be alive! Mayor Daley and the Chicago political machine! The riot at the Democratic National Convention! Abbie Hoffman, Jerry Rubin! Come find out more about this pivotal era in American history, with this immersive experience through Chicago's 1960s nightlife. The tour starts at the elegant Drake Hotel, where you'll learn what they were talking about when they talked about night life in the 60s. Talk will focus on the Playboy Club and Hugh Hefner -- what would a 60s Chicago tour be without them? You'll meander along the Gold Coast, enjoying one of Chicago's most scenic and historic neighborhoods, complete with mansions and gaslights. Finally, you'll enter the famous Pump Room, destination for scores of celebrities; you'll even see Frank Sinatra’s booth. That’s right, Ol’ Blue Eyes himself. With all the fascinating scenery, history, and culture… What’s not to love?
    1960s Nightlife in the Gold Coast

    140 E Walton Pl, Chicago

    • Enjoy an interactive experience focused on the nightlife in 1960’s Chicago
    • Start your tour at the Drake Hotel, one of the most elegant places in the city
    • Check out the Pump Room, a favored haunt by many celebrities, including the Chairman of the Board himself, Frank Sinatra
    • Learn about Hugh Hefner and the Playboy Club
    BOOK NOW ← Back
  • Book Now

    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
    BOOK NOW ← Back
  • Book Now

    1960's Nightlife in the Gold Coast Tour

    Mad about the 1960s? Get in touch with Chicago's seismic past with a sweeping walk through time! Journey alongside a local guide and historian, and enjoy fun facts and anecdotes designed to bring the past to life. Video, music, and vintage images help further shade modern-day destinations in black and white, and technicolor. The infamous Drake Hotel is up first for a peek at a provocative nightlife underscored by the Playboy Club and the influence of Hugh Hefner. Then, it's on to Rush Street, where class and vice used to dance arm in arm. A meander among the mansions and gaslights of the Gold Coast are up next, before ending your racy walk at the Pump Room, where Frank Sinatra kept a private booth, and celebrities came to unwind. Better bring a hanky. You’re going to need something to wipe that brow with.
    1960's Nightlife in the Gold Coast Tour

    140 E Walton Pl, Chicago

    • Explore 1960s Chicago on this multimedia nightlife tour
    • Visit the Drake Hotel, Rush Street, the Gold Coast, and the Pump Room
    • Overlay the experience with video, music, and vintage photographs
    • Sweep your imagination back to an era that now seems strangely foreign
    BOOK NOW ← Back
  • Book Now

    Glide at Night Segway Tour

    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
    BOOK NOW ← Back
    5 positive reviews

Kind words from our customers