The river & the skyline
Chicago
Architecture cruises, food walks, the river, and the lake — city days, not just boat days.
The river & the skyline
Chicago
Architecture cruises, food walks, the river, and the lake — city days, not just boat days.
What’s on
All Chicago listings60 experiences from independent operators.
1 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
1 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
1 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
1 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
18 FT Private Pontoon Cruise
Hosted by Chicago Boat Rentals · Chicago, Illinois
24 ft12
from $150 / day
2 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
2 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
2 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
2 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
2026 Air & Water Show - Special Event!
Hosted by Tall Ship Windy · Chicago, Illinois
Tour
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22 FT Private Pontoon Cruise (Up to 10 People)
Hosted by Chicago Boat Rentals · Chicago, Illinois
24 ft12
from $350 / day
37ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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4 Hour BMX Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
4 Hour Dirt Jumper Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
4 Hour Kids Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
4 Hour Mountain Bike Rentals
Hosted by Big Marsh Park · Chicago, Illinois
22 ft12150 HP
See dates for price
46ft. Sea Ray Express
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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48ft. Sea Ray Flybridge
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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50ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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52ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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56ft. Sea Ray Sundancer
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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57ft. Power Catamaran
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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72ft. Classic Chris Craft
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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78ft. Power Catamaran
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Acura NSX
Hosted by DS Luxury · Chicago, Illinois
Adventure
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All That Glam: Chicago’s Art Deco Masterpieces
Hosted by Inside Chicago Walking Tours · Chicago, Illinois
Tour
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Art Institute of Chicago Skip-the-Line Tour (Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
from $95 / trip
Art Institute of Chicago Skip-the-Line Tour (Semi-Private)
Hosted by Babylon Tours Chicago · Chicago, Illinois
Tour
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Art Institute of Chicago Tour by Art Historian with Skip-the-Line Tickets (Priva
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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Art Institute of Chicago Tour with Skip-the-Line Tickets (Semi Private)
Hosted by Chicago Museum Tours LLC · Chicago, Illinois
Tour
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Aston Martin DB 11
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DB12 Volante
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DBS
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin DBX 707
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Aston Martin Vantage
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi R8
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi R8 Spyder
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Audi RS Q8
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Beautiful Interiors and The Bean
Hosted by Chicago by Dave · Chicago, Illinois
Adventure
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Bentley Bentayga
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Continental GTC
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Continental GTC
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Flying Spur
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Bentley Flying Spur Mulliner
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Beverly Tour
Hosted by Brick of Chicago · Chicago, Illinois
Tour
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Bikes, Bites & Views: Chicago's Signature Dishes Bike Tour - Adults (Ages 16+)
Hosted by Bobby's Bike Hike · Chicago, Illinois
Tour
from $79 / trip
Cadillac Escalade
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Cadillac Escalade V
Hosted by DS Luxury · Chicago, Illinois
Adventure
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Capt Michael Gabiga
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Adrian Tejeda
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Alex Castillo
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Brian Haas
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Chase Curtis
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Dan Leslie
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Dave Krell
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain David Groover
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
from $100 / trip
Captain Doug Scroggins
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Ian Barbosa
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Jonathan Zietlow
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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Captain Justin Pasciak
Hosted by Knot My Boat Charters · Chicago, Illinois
Tour
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