With the 1848 arrival of the railroad and the Illinois and Michigan Canal to Chicago, the city began its unprecedented boom. Alongside the growth of business came the explosion of the city’s infamous underworld.
Join us on Friday, Saturday, and Sunday evenings at 7:00 PM as we offer our unique take on Nelson Algren’s “Hustlertown, USA”. Kayak the Chicago River as the sun sets into twinkling darkness and experience the legacy of our nefarious gangsters. Night time paddling is beautiful – come enjoy the scene with us!
You will learn about the city’s early Wild West reputation; how one man rose from poverty to become the most powerful man the city has ever seen; how one area of the river purportedly became haunted; why everyone in Chicago feared a man the size of a child; and all about the world-renowned Italian crime lineage including the likes of mobsters Jim Colosimo, Johnny Torrio, and, of course, Al Capone.
WhenFriday, Saturday, and Sunday nights
Click here for calendar
Times7:00 PM to 9:30 PM
Price$65 per person
InclusionsSingle or double kayak, life vest, paddle, guide(s), paddling lesson, dry bags, sunscreen
OptionsKids under 16 are $45 per person, and must ride in a double kayak with a guardian. Children too small to paddle can ride in the middle of a double at no charge. Parental discretion is advised for this tour
BringWater-friendly clothing and shoes. Blue jeans not recommended. Bring electronics at your own risk
Weight limitsSingle kayak - 275 lbs (approx); Double kayak - 435 lbs (approx)
At the beginning of the tour, we teach the basics of flat water kayaking, have a river safety briefing, get you outfitted with the correct boat, and get the group on the water.
The group paddles to a series of locations we have chosen for the view and historical significance. Our guides make sure everyone stays safe from boat traffic and obstacles.
As Chicago expanded and modernized, the criminal underworld rapidly developed and became part of the fabric of the town’s history. This tour covers many sordid personalities; from the little-known gangster bosses of the nineteenth century to the infamous linage of Italian mobsters. The keys to the city are routinely wrestled back and forth as different factions fight for their share of the power. Triumphs and tragedies define the Chicago’s history -- likewise 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. Snap some quality pictures of the city both at sunset and at night as the day slips away into darkness and the shady side of the Second City awakens.
Take some final snapshots of the gorgeous nighttime skyline before a short paddle back to the dock, where we get everyone safely out of the water.
Emily G: We all so enjoyed ourselves. The guides were fun and informative and it was a really great evening...
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...