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2,175 High-End Indian motorcycles for sale in Chicago, IL

Indian Challenger Indian Chief Indian Chieftain Indian FTR Indian Pursuit Indian Roadmaster Indian Scout Indian Spirit Indian Sport Scout Indian Springfield Indian Super Chief Indian Super Scout Indian eFTR
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Location 500m from Chicago, IL ☒
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Average for High-End : 1,198cc
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Average for High-End : 31″
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1 - 24 of 2,175
Most recent Most expensive Least expensive Nearest Most valuable
2019 Indian Motorcycle Chieftain® Classic Icon Series
$19,994
Mileage 12,224m
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2024 Indian Chieftain Limited Spirit Blue Metallic
♡
2024 Indian Chieftain Limited Spirit Blue Metallic
$29,749
New
Location West Bend, WI (124mi)
👤 
Fuel Powersports
2016 Indian Motorcycle® SCOUT
$5,799
Mileage 13,354m
Great Price
Low Mileage
Location Big Bend, WI (84mi)
👤 
Road Track & Trail
2016 Indian Motorcycle® Springfield™ Indian Motorcycle® Red
$9,799
Mileage 5,459m
Great Price
Low Mileage
Location Big Bend, WI (84mi)
👤 
Road Track & Trail
2009 Indian Motorcycle® Chief Standard
$7,999
Mileage 19,634m
Location Richmond, MI (288mi)
👤 
Ball Equipment Richmond
2024 Indian Motorcycle Pursuit® Dark Horse®
$35,999
New
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2024 Indian Motorcycle Chieftain® Dark Horse®
$30,749
New
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2024 Indian Motorcycle Chief Bobber Dark Horse®
$19,999
New
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2024 Indian Motorcycle Sport Chief
$20,499
New
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2018 Indian Motorcycle Roadmaster® ABS
$19,994
Mileage 8,883m
Good Price
Low Mileage
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2021 Indian Motorcycle® Roadmaster® Limited Thunder Black Azure Crystal
$13,999
Mileage 73,517m
Location Big Bend, WI (84mi)
👤 
Road Track & Trail
2019 Indian Motorcycle FTR 1200
$8,184
Mileage 7,443m
Good Price
Location Nashville, TN (446mi)
👤 
Nashville Motos
2024 Indian Challenger Black Metallic
♡
2024 Indian Challenger Black Metallic
$26,499
New
Location West Bend, WI (124mi)
👤 
Fuel Powersports
2020 Indian Motorcycle® Springfield® Burgundy Metallic / Titanium Metallic
$12,999
Mileage 13,943m
Great Price
Location Big Bend, WI (84mi)
👤 
Road Track & Trail
2017 Indian Chief Vintage Willow Green Over Ivory Cream Vintage
$13,499
Mileage 22,312m
Location Shelby Township, MI (271mi)
👤 
Triumph Detroit
2021 Indian Motorcycle Roadmaster Limited
$20,577
Mileage 154m
Great Price
Low Mileage
Location Olathe, KS (483mi)
👤 
Rawhide Harley-Davidson®
2023 Indian Pursuit Dark Horse With Premium Package Silver Qua
$27,487
New
Great Price
Location Waukesha, WI (94mi)
👤 
Action Power Sports
2020 Indian Motorcycle Challenger® Limited
$20,994
Mileage 944m
Great Price
Low Mileage
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2022 Indian Motorcycle Chieftain®
$17,494
Mileage 10,384m
Good Price
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2023 Indian Motorcycle Sport Chief Dark Horse®
$16,994
Mileage 1,811m
Low Mileage
Location Charleston, IL (187mi)
👤 
Indian Motorcycle® Central Illinois
2024 Indian Challenger Dark Horse Spirit Blue Smoke
$30,499
New
Location West Bend, WI (124mi)
👤 
Fuel Powersports
2024 Indian Chieftain Dark Horse W/Powerband Audio Pkg Ghost
$31,999
New
Location West Bend, WI (124mi)
👤 
Fuel Powersports
2022 Indian Motorcycle® FTR S White Smoke
$9,799
Mileage 6,706m
Great Price
Location Big Bend, WI (84mi)
👤 
Road Track & Trail
2024 Indian Chieftain® Dark Horse®
$30,749
New
Location Ottumwa, IA (285mi)
👤 
RJ Powersports Ottumwa
1 - 24 of 2,175
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Rent & test before you buy! Get $25 off your first ride on Riders Share