Indian Challenger Motorcycles for sale Near Kalamazoo, MI

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Find 35 Indian Challenger motorcycles for sale near Kalamazoo, MI from dealers and private sellers on Cycle Trader. There are currently 20 new and 15 used Indian Challenger motorcycles for sale with an average price of $26,249, ranging from $16,500 to $29,749.

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42

2022 Indian Motorcycle® Challenger® Black Metallic in Romeoville, IL

Used 2022 Indian Motorcycle® Cruiser

Challenger® Black Metallic

2022 Indian Motorcycle Challenger Black Metallic, 1 OWNER BIKE, very well maintained, has low miles, exhaust upgrade, speakers upgrade.<br /> <br /> 2

2021 Indian CHALLENGER DARK HORSE DARK HORSE in Mchenry, IL

Used 2021 Indian Cruiser

CHALLENGER DARK HORSE DARK HORSE

Power Plus with 122hp and 128ft-lbs of torque. 7" Ride Command with Apple CarPlay integration. Smart Lean Technology. Dynamic Traction $ ABS with corn

2025 Indian Motorcycle Challenger® Limited with PowerBand Audio Package LIMITED WITH POWERBAND AUDIO PACKAGE in Racine, WI

Used 2025 Indian Motorcycle Cruiser

Challenger® Limited with PowerBand Audio Package LIMITED WITH POWERBAND AUDIO PACKAGE

Stock # I440253

<p style="margin-bottom: 1em;">New used bike. 1 mile. Comes with 1 year of coverage from the date of purchase. </p><p style="margin-bottom: 1em;">A

Indian Motorcycle of Racine

2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke DARK HORSE in Kalamazoo, MI

New 2026 Indian Motorcycle® Cruiser

Challenger® Dark Horse® Black Smoke DARK HORSE

Stock # T3443136

2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke, 2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke <p>Featuring a chassis-mounte

Zeigler Motorsports

2021 Indian Challenger Limited Ruby Metallic Limited Thunder Bla LIMITED in Coldwater, MI

Used 2021 Indian Cruiser

Challenger Limited Ruby Metallic Limited Thunder Bla LIMITED

2021 Indian Challenger Limited Ruby Metallic Limited Thunder Black Pearl, 2021 Indian Motorcycle® Challenger® Limited Thunder Black Pearl <p><strong>F

Planet Powersports

2020 Indian Motorcycle Challenger® Limited LIMITED in Elkhart, IN

Used 2020 Indian Motorcycle Cruiser

Challenger® Limited LIMITED

Stock # EIM390322

Elkhart Indian Motorcycle

2025 Indian Motorcycle Challenger® in Racine, WI

New 2025 Indian Motorcycle Cruiser

Stock # I440119

<p style="margin-bottom: 1em;">**priced with all All applicable rebates"</p><p style="margin-bottom: 1em;">Save $3500 with trade in assistance and cus

Indian Motorcycle of Racine

2021 Indian Motorcycle Challenger Limited Deepwater Metallic LIMITED in Elmhurst, IL

Used 2021 Indian Motorcycle Cruiser

Challenger Limited Deepwater Metallic LIMITED

2021 Indian Motorcycle Challenger Limited Deepwater Metallic, Prices include all available factory promotions and rebates

2026 Indian Motorcycle® Challenger® Dark Horse® Deep Blue Metallic DARK HORSE in Monee, IL

New 2026 Indian Motorcycle® Cruiser

Challenger® Dark Horse® Deep Blue Metallic DARK HORSE

2026 Indian Motorcycle® Challenger® Dark Horse® Deep Blue Metallic, 2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke <p>Featuring a chassis

Gina's Motorsports

2021 Indian Motorcycle Challenger® in Wauconda, IL

Used 2021 Indian Motorcycle Cruiser

<p>Used 2021 Indian Challenger for sale in Wauconda, IL at Monster Powersports. Fully Serviced Certified Pre-Owned motorcycles are ready to ride! Fina

Monster Powersports

2026 Indian Motorcycle Challenger® Limited LIMITED in Muskego, WI

New 2026 Indian Motorcycle Cruiser

Challenger® Limited LIMITED

Stock # IND440834

<p>RECEIVE A STAGE 1 SLIP ON EXHAUST AND TIPS WITH THE PURCHASE OF THIS CHALLENGER! $1500 TRADE BONUS IS BASED OFF A QUALIFYING TRADE-IN</p><p style="

Indian Motorcycles of Metro Milwaukee

2021 Indian Motorcycle® Challenger® Limited Thunder Black Pearl LIMITED in Big Bend, WI

Used 2021 Indian Motorcycle® Touring

Challenger® Limited Thunder Black Pearl LIMITED

2021 Indian Motorcycle® Challenger® Limited Thunder Black Pearl, ONLY 6627 MILES, 1-OWNER, INDIAN UPGRADED EXHAUST, UPGRADED HIGH FLOW INTAKE, NAVIGAT

Road Track And Trail

2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke DARK HORSE in Clinton Twp, MI

New 2026 Indian Motorcycle® Cruiser

Challenger® Dark Horse® Black Smoke DARK HORSE

2026 Indian Motorcycle® Challenger® Dark Horse® Black Smoke, Receive up to $1,500 in trade bonus with qualified trade. Offer expires 10/31/2026. Price

Clinton Twp, MI

2024 Indian Motorcycle® Challenger® Limited with PowerBand Audio Package Ghost LIMITED WITH POWERBAND AUDIO PACKAGE in Kalamazoo, MI

New 2024 Indian Motorcycle® Cruiser

Challenger® Limited with PowerBand Audio Package Ghost LIMITED WITH POWERBAND AUDIO PACKAGE

Stock # r3432349

2024 Indian Motorcycle® Challenger® Limited with PowerBand Audio Package Ghost White Metallic, 2024 Indian Motorcycle® Challenger® Limited with PowerB

Zeigler Motorsports

2023 Indian Motorcycle® Challenger® Limited Black Metallic LIMITED in Kalamazoo, MI

New 2023 Indian Motorcycle® Cruiser

Challenger® Limited Black Metallic LIMITED

Stock # P3415687

2023 Indian Motorcycle® Challenger® Limited Black Metallic, 2023 Indian Motorcycle® Challenger® Limited Black Metallic <p><strong>Features may include

Zeigler Motorsports

2024 Indian Motorcycle® Challenger® Titanium Smoke in Kalamazoo, MI

New 2024 Indian Motorcycle® Cruiser

Challenger® Titanium Smoke

Stock # R3429948

2024 Indian Motorcycle® Challenger® Titanium Smoke, 2024 Indian Motorcycle® Challenger® Titanium Smoke <ul><li>FREE REIN TO DOMINATE</li></ul><p>Our P

Zeigler Motorsports

2026 Indian Motorcycle Challenger® Dark Horse® DARK HORSE in Elkhart, IN

New 2026 Indian Motorcycle Cruiser

Challenger® Dark Horse® DARK HORSE

Stock # IND441216

A chassis-mounted fairing, bold, distinctive styling, and modern amenities provide everything you need in a modern day bagger.

Elkhart Indian Motorcycle

2026 Indian Motorcycle Challenger® Dark Horse® DARK HORSE in Elkhart, IN

New 2026 Indian Motorcycle Cruiser

Challenger® Dark Horse® DARK HORSE

Stock # IND445887

A chassis-mounted fairing, bold, distinctive styling, and modern amenities provide everything you need in a modern day bagger.

Elkhart Indian Motorcycle

2026 Indian Motorcycle Challenger® Limited LIMITED in Elkhart, IN

New 2026 Indian Motorcycle Cruiser

Challenger® Limited LIMITED

Stock # IND444967

Featuring a chassis mounted fairing, premium chrome finishes, and the 108 cu-in liquid-cooled PowerPlus engine with 122 HP.

Elkhart Indian Motorcycle

2021 Indian Motorcycle Challenger® Limited LIMITED in Elkhart, IN

Used 2021 Indian Motorcycle Cruiser

Challenger® Limited LIMITED

Stock # EIM400487

<p>LOW mileage and CLEAN bike that is ready to RIDE!</p><p style="margin-bottom: 1em;"><strong>Price includes dealer set-up cost</strong></p>

Elkhart Indian Motorcycle

2023 Indian Motorcycle Challenger® in Racine, WI

Used 2023 Indian Motorcycle Cruiser

Stock # I406786

A frame-mounted fairing, bold, distinctive styling, and modern amenities provide everything you need in a modern day bagger.

Indian Motorcycle of Racine

2026 Indian Motorcycle Challenger Dark Horse Deep Blue Metallic DARK HORSE in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Dark Horse Deep Blue Metallic DARK HORSE

Stock # PI26077

2026 Indian Motorcycle Challenger Dark Horse Deep Blue Metallic, Prices include all available factory promotions and rebates

2026 Indian Motorcycle Challenger Limited Nara Bronze Metallic LIMITED in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Limited Nara Bronze Metallic LIMITED

Stock # PI26068

2026 Indian Motorcycle Challenger Limited Nara Bronze Metallic, Prices include all available factory promotions and rebates

2026 Indian Motorcycle Challenger Dark Horse Black Smoke DARK HORSE in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Dark Horse Black Smoke DARK HORSE

Stock # PI26078

2026 Indian Motorcycle Challenger Dark Horse Black Smoke, Prices include all available factory promotions and rebates

2026 Indian Motorcycle Challenger Dark Horse Sunset Red Smoke DARK HORSE in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Dark Horse Sunset Red Smoke DARK HORSE

Stock # PI26079

<p>Experience the power and style of the Indian Motorcycle Challenger Dark Horse. This New 2026 Indian Motorcycle Challenger Dark Horse Sunset Red Smo

2026 Indian Motorcycle Challenger Dark Horse Signature Series Abyss Metallic / DARK HORSE in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Dark Horse Signature Series Abyss Metallic / DARK HORSE

Stock # PI26168

2026 Indian Motorcycle Challenger Dark Horse Signature Series Abyss Metallic / Red Allert, Prices include all available factory promotions and rebates

2026 Indian Motorcycle Challenger Limited Black Metallic LIMITED in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Limited Black Metallic LIMITED

Stock # PI26066

2026 Indian Motorcycle Challenger Limited Black Metallic, Prices include all available factory promotions and rebates

2026 Indian Motorcycle Challenger Limited Crimson LIMITED in Elmhurst, IL

New 2026 Indian Motorcycle Cruiser

Challenger Limited Crimson LIMITED

Stock # PI26067

2026 Indian Motorcycle Challenger Limited Crimson, Prices include all available factory promotions and rebates

2020 Indian Motorcycle Challenger Titanium Metallic BASE in Elmhurst, IL

Used 2020 Indian Motorcycle Cruiser

Challenger Titanium Metallic BASE

<p>Experience the thrill of the open road with the 2020 Indian Motorcycle Challenger Titanium Metallic. This used motorcycle is perfect for cruising a

2020 Indian Motorcycle Challenger Limited Thunder Black Pearl LIMITED in Elmhurst, IL

Used 2020 Indian Motorcycle Cruiser

Challenger Limited Thunder Black Pearl LIMITED

2020 Indian Motorcycle Challenger Limited Thunder Black Pearl, Prices include all available factory promotions and rebates

2022 Indian Motorcycle Challenger Limited Maroon Metallic LIMITED in Elmhurst, IL

Used 2022 Indian Motorcycle Cruiser

Challenger Limited Maroon Metallic LIMITED

<p>Experience the thrill of the open road with this striking machine.</p> <p>Used 2022 Indian Motorcycle Challenger Limited Maroon Metallic. This mot

2023 Indian Motorcycle Challenger Dark Horse Titanium Smoke DARK HORSE in Elmhurst, IL

Used 2023 Indian Motorcycle Cruiser

Challenger Dark Horse Titanium Smoke DARK HORSE

<p>Experience the thrill of the open road with this striking cruiser. This used 2023 Indian Motorcycle Challenger Dark Horse Titanium Smoke is designe

2021 Indian Motorcycle Challenger Thunder Black in Elmhurst, IL

Used 2021 Indian Motorcycle Cruiser

Challenger Thunder Black

<p>This Challenger has 10,779 miles on the odometer, showcasing its reliability and readiness for new journeys. Prices include all available factory p

2026 Indian Motorcycle® Challenger® Limited Black Metallic LIMITED in Monee, IL

New 2026 Indian Motorcycle® Cruiser

Challenger® Limited Black Metallic LIMITED

2026 Indian Motorcycle® Challenger® Limited Black Metallic, 2026 Indian Motorcycle® Challenger® Limited Crimson <p>Featuring a chassis mounted fairing

Gina's Motorsports

2026 Indian Motorcycle Challenger® Dark Horse® DARK HORSE in Muskego, WI

New 2026 Indian Motorcycle Cruiser

Challenger® Dark Horse® DARK HORSE

Stock # IND441984

<p>RECEIVE A STAGE 1 SLIP ON EXHAUST AND TIPS WITH THE PURCHASE OF THIS CHALLENGER! $1500 TRADE BONUS IS BASED OFF A QUALIFYING TRADE-IN</p><p style="

Indian Motorcycles of Metro Milwaukee

Available Years

2026 Indian CHALLENGER - 16 motorcycles
2021 Indian CHALLENGER - 7 motorcycles
2020 Indian CHALLENGER - 3 motorcycles

2023 Indian CHALLENGER - 3 motorcycles
2022 Indian CHALLENGER - 2 motorcycles
2024 Indian CHALLENGER - 2 motorcycles

2025 Indian CHALLENGER - 2 motorcycles

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