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21 High-End Cruiser motorcycles for sale in Chicago, IL

American IronHorse BMW Big Dog Boss Hoss Bourget Buell CFMOTO Can-Am Ducati Excelsior-Henderson Harley-Davidson Honda Hyosung Indian Kawasaki LiveWire Moto Guzzi Royal Enfield Suzuki Triumph Victory Yamaha
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Cruiser ☒ CATEGORY
High-End ☒ LOCATION
Location 10m from Chicago, IL ☒
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Average for Cruiser / High-End : 1,737cc
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Average for Cruiser/ High-End : 27.2″
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1 - 21 of 21
Most recent Most expensive Least expensive Nearest Most valuable
2019 Ducati XDiavel S
$13,800 $14,900
Mileage 1,788m
Good Price
Low Mileage
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2026 Ducati XDiavel V4
$27,495
New
Good Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2020 Ducati XDiavel S
$14,900 $15,900
Mileage 6,762m
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Triumph Rocket 3 Storm GT
$27,795
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Ducati Diavel V4
$27,495
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2026 Ducati Diavel V4 RS
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2022 Triumph Rocket 3 GT
$10,750 $14,900
Mileage 6,846m
Great Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2023 Ducati XDiavel S
$13,450 $19,900
Mileage 4,606m
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2024 Ducati Diavel V4
$21,995 $23,495
New
Great Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2026 Ducati XDiavel V4
$29,295
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2026 Ducati XDiavel V4
$28,995
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2024 BMW R 18 Base
$11,995 $16,400
New
Great Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Triumph Rocket 3 GT Evel Knievel Limited Edition
$28,295
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Ducati Diavel V4
🏠 Delivery
♡
2025 Ducati Diavel V4
$27,195
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Triumph Rocket 3 R Evel Knievel Limited Edition
$27,495
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Triumph Rocket 3 Storm R
$24,995
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2025 Triumph Rocket 3 Storm GT
$24,995
New
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2024 Ducati Diavel V4
$21,995 $26,995
New
Good Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2024 BMW R 18 Roctane
$14,995 $19,645
New
Good Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2024 BMW R 18 Roctane
$12,995 $20,035
New
Great Price
Location Chicago, IL (1mi)
👤 
Motoworks Chicago
2002 yamaha XV1700
$2,995
Mileage 40,842m
Location Forest View, IL (11mi)
👤 
Tool Store Go Kart Shop
1 - 21 of 21
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Rent & test before you buy! Get $25 off your first ride on Riders Share