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277 High-End Indian Touring motorcycles for sale in Chicago, IL

Indian Challenger Indian Challenger Powerplus Indian Chieftain Indian Chieftain Powerplus Indian Pursuit Indian Roadmaster Indian Roadmaster Powerplus Indian Springfield
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Location 25m from Chicago, IL ☒
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Average for Touring / High-End : 1,811cc
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Average for Touring/ High-End : 27.8″
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1 - 24 of 277
Most recent Most expensive Least expensive Nearest Most valuable
2018 Indian Motorcycle® Roadmaster® ABS Thunder Black
♡
2018 Indian Motorcycle® Roadmaster® ABS Thunder Black
Mileage 4,692m
Low Mileage
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2017 Indian Motorcycle® N17TCNAAAS
♡
2017 Indian Motorcycle® N17TCNAAAS
Mileage 16,915m
Low Mileage
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2016 Indian Motorcycle® Roadmaster® Steel Gray and Thunder Black
♡
2016 Indian Motorcycle® Roadmaster® Steel Gray and Thunder Black
$11,999
Mileage 25,901m
Great Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2021 Indian Motorcycle® Challenger® Limited Deepwater Metallic
♡
2021 Indian Motorcycle® Challenger® Limited Deepwater Metallic
$15,999
Mileage 35,599m
Great Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2017 Indian Motorcycle® Roadmaster® Willow Green Over Ivory Cream
$16,499
Mileage 25,690m
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2017 Indian Motorcycle® Chieftain® Wildfire Red Over Thunder Black
$12,799 $12,999
Mileage 13,126m
Good Price
Low Mileage
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2024 Indian Motorcycle® Roadmaster® Black Metallic/Titanium Metallic
$25,999 $26,349
Used
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2019 Indian Motorcycle® Chieftain® Classic Icon Series Willow Green/Ivory Cream
$19,499
Mileage 1,844m
Low Mileage
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2020 Indian Motorcycle® Challenger Limited Deepwater Metallic
$14,999
Mileage 31,709m
Great Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2015 Indian Motorcycle® Chieftain® Thunder Black
$10,499 $10,799
Mileage 18,119m
Low Mileage
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2018 Indian Motorcycle® Roadmaster® ABS Polish.Bronze Over Thund.Black w/Silver Pinst.
$13,799 $14,499
Mileage 26,348m
Great Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Deep Blue Metallic with B
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Deep Blue Metallic with B
$38,749
New
Good Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Heavy Metal
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Heavy Metal
$39,499
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Challenger® Dark Horse® 112 w/PowerBand Audio Black Crystal w/Black Metalli
♡
2026 Indian Motorcycle® Challenger® Dark Horse® 112 w/PowerBand Audio Black Crystal w/Black Metalli
$35,999
New
Good Price
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Black Smoke
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Black Smoke
$38,749
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 Maroon Metallic
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 Maroon Metallic
$37,749
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Maroon Metallic
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Maroon Metallic
$39,499
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Ghost White Metallic with
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 w/PowerBand Ghost White Metallic with
$40,249
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Deep Blue Metallic with Black M
♡
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Deep Blue Metallic with Black M
$40,249
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Ghost White Metallic with Black
♡
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Ghost White Metallic with Black
$40,249
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 Ghost White Metallic with Black Metal
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® 112 Ghost White Metallic with Black Metal
$38,499
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® Black Smoke
♡
2026 Indian Motorcycle® Roadmaster® PowerPlus Dark Horse® Black Smoke
$33,999
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 Black Smoke
♡
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 Black Smoke
$36,999
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Maroon Metallic
♡
2026 Indian Motorcycle® Pursuit® Dark Horse® 112 w/ PowerBand Audio Maroon Metallic
$39,499
New
Location Elmhurst, IL (18mi)
👤 
iMotorsports Chicago
1 - 24 of 277
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Riders Share

Rent & test before you buy! Get $25 off your first ride on Riders Share