With the 1848 arrival of the railroad and the Illinois and Michigan Canal to Chicago, the city accelerated its unprecedented boom. In lockstep with the growth of business and speculation came the explosion of the city’s infamous underworld.
Join us in the evenings as we offer our unique take on writer Nelson Algren’s “Hustlertown, USA”. Kayak down the Chicago River with us as the sun sets into twinkling darkness and experience the legacy of our nefarious gangsters. Night time paddling is beautiful – come enjoy the scene!
On this tour, you will learn about the city’s early Wild West reputation, how one man rose from poverty to become the most powerful man in our city’s history, how one area of the river purportedly became haunted, why everyone in nascent Chicago feared a man the size of a child, and all about the larger-than-life Italian crime lineage including the likes of mobsters Jim Colosimo, Johnny Torrio, and, of course, Al Capone.
DurationOn-water: ~2 hours
Orientation/Launch: ~25 minutes
Ticket Price$65 per adult
$45 per child (under 16)
OptionsChildren small enough to fit in child seat are free (usually 2-4 years old).
Parental discretion is advised for this tour.
InclusionsSingle or double kayak (choose upon arrival), life vest, paddle, guide(s), safety orientation, paddling lesson
AttireComfortable, water-friendly clothing and shoes are suggested, as you will likely get wet. Denim not recommended. Dress for the weather on the day of the event.
Weight limitsSingle kayak - 275 lbs (approx.); Double kayak - 500 lbs (approx.)
Private OptionIf you are interested in this tour, but are unable to go at one of our scheduled times, send us an email at firstname.lastname@example.org to request a private or semi-private tour!
At the beginning of each tour, we teach the basics of flat water kayaking and brief our guests on river safety in a 10 minute orientation session.
We paddle as a group to a series of locations that we have chosen for the view, safety, and their historical significance. Our guides make sure everyone stays safe from boat traffic and obstacles.
This tour covers many sordid personalities; from the little-known gangster bosses of the nineteenth century to the infamous lineage of Italian mobsters. Alliances form and dissolve just as quickly as different factions fight for their share of power. We present the good and the bad as we discuss the kings and queens of vice of Chicago’s past.
Find yourself floating on the brightly illuminated surface of the river as it reflects the twinkling, golden lights of the city above. Enjoy fantastic photo opportunities as the day slips into darkness and the ghosts of Chicago's gangster past awaken!
Take some final snapshots of the gorgeous nighttime skyline before a short paddle back to the dock, where we assist everyone out of the water. Numerous dining options in the area are still open if you are feeling hungry!
Susan A: We decided to do their Shady Chicago: Ghosts and Gangsters tour on our last night in town...and we were so glad we did...The weather was perfect, the staff was incredibly friendly and knowledgeable and the tour was the perfect length. To be on the water at night with the lights of Chicago all around you is truly worth the price of admission.
ILroadies: The location of the dock is perfect. Overall great experience, we will definitely return for another kayak excursion...
Jessica C: Kayaking was a lot of fun! Very friendly tour guide and all levels of kayakers welcome and comfortable...