Indian Chieftain Motorcycles for sale

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Find 569 Indian Chieftain motorcycles for sale from dealers and private sellers on Cycle Trader. There are currently 143 new and 426 used Indian Chieftain motorcycles for sale with an average price of $19,199, ranging from $10,996 to $32,249.

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42

2024 Indian Motorcycle® Chieftain® Dark Horse® Ghost White Metallic Smoke DARK HORSE in Farmers Branch, TX

Used 2024 Indian Motorcycle® Cruiser

Chieftain® Dark Horse® Ghost White Metallic Smoke DARK HORSE

2024 Indian Motorcycle® Chieftain® Dark Horse® Ghost White Metallic Smoke, YOU ARE LOOKING AT A 2024 INDIAN CHIEFTAIN DARKHORSE WITH 2,344 MILES ON IT

Dream Machines Of Texas

Farmers Branch, TX

2015 Indian Chieftain Indian RedThunder Black BASE in Austin, TX

Used 2015 Indian Touring

Chieftain Indian RedThunder Black BASE

Stock # UIN320627F

<p>Experience the open road with this touring motorcycle. This used 2015 Indian Chieftain Indian RedThunder Black BASE offers a blend of comfort and p

2017 Indian Motorcycle CHIEFTAIN LIMITED LIMITED in Panama City Beach, FL

Used 2017 Indian Motorcycle Touring

CHIEFTAIN LIMITED LIMITED

<p>COME CHECK OUT THIS CLASSIC LOOK CHIEFTAIN !!!!!EQUIPPED WITH A PASSENGER BACK REST W/ LUGGAGE RACK, HWY PEGS & RIDERS BACKREST.WOW</p><p style="ma

Indian Motorcycle of Panama City Beach

Panama City Beach, FL

2018 Indian Motorcycle Chieftain® Limited ABS LIMITED in Brooksville, FL

Used 2018 Indian Motorcycle Cruiser

Chieftain® Limited ABS LIMITED

Stock # IND359413

<p>Build your legend as the leader of the pack.</p>There's one in every pack. At the front. Take the lead with Chieftain® Limited. Featuring aggressiv

Brooksville, FL

2019 Indian Chieftain Dark Horse Bronze Smoke DARK HORSE in Greeneville, TN

Used 2019 Indian Touring

Chieftain Dark Horse Bronze Smoke DARK HORSE

Stock # UM379866

2019 Indian Chieftain Dark Horse Bronze Smoke, 2019 Indian Motorcycle® Chieftain Dark Horse® Bronze Smoke <p><strong>Features may include:</strong></p

Mountain Motorsports - Greeneville

Greeneville, TN

2019 Indian Chieftain Limited Thunder Black Pearl LIMITED in Coldwater, MI

Used 2019 Indian Cruiser

Chieftain Limited Thunder Black Pearl LIMITED

2019 Indian Chieftain Limited Thunder Black Pearl, 2019 Indian Motorcycle® Chieftain® Limited Thunder Black Pearl <strong>New, streamlined styling mee

Planet Powersports

2020 Indian Motorcycle Chieftain® in Adams Center, NY

Used 2020 Indian Motorcycle Cruiser

Stock # 24P0410

<p>TWO THUNDER STROKE V-TWIN OPTIONS</p><p style="margin-bottom: 1em;">Choose the new, more powerful Thunder Stroke 116 engine producing 126 ft-lbs of

Waite Motorsports

Adams Center, NY

2019 Indian Motorcycle® Chieftain® Steel Gray BASE in Conneaut Lake, PA

Used 2019 Indian Motorcycle® Cruiser

Chieftain® Steel Gray BASE

2019 Indian Motorcycle® Chieftain® Steel Gray, 2019 Indian Motorcycle® Chieftain® Steel Gray <strong>Aggressive style. Unrivaled bagger performance.</

STREET TRACK 'N' TRAIL

Conneaut Lake, PA

2025 Indian Motorcycle CHIEFTAIN DARK HORSE, STORM GRAY, 50S Dark Horse® DARK HORSE in Vernon, CT

Used 2025 Indian Motorcycle Cruiser

CHIEFTAIN DARK HORSE, STORM GRAY, 50S Dark Horse® DARK HORSE

Stock # S3431818

2025 Indian Motorcycle CHIEFTAIN DARK HORSE, STORM GRAY, 50S Dark Horse®, Powered by the legendary Thunderstroke 116 giving you more power, more techn

Scranton Powersports

2024 Indian Motorcycle Chieftain® Limited with PowerBand Audio Package LIMITED WITH POWERBAND AUDIO PACKAGE in Elk Grove, CA

Used 2024 Indian Motorcycle Cruiser

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

Stock # UIND422741

<p style="margin-bottom: 1em;">All the same features of the Chieftain Dark Horse in a class package of premium metallic paints and chrome finishes.</p

Elk Grove Power Sports

2022 Indian Motorcycle CHIEFTAIN LIMITED LIMITED in Raleigh, NC

Used 2022 Indian Motorcycle Touring

CHIEFTAIN LIMITED LIMITED

Stock # UI-3404748

<p>Experience the open road with confidence. This Used 2022 Indian Motorcycle CHIEFTAIN LIMITED offers a blend of comfort and performance. Ideal for l

2024 Indian Motorcycle Chieftain® Limited with PowerBand Audio Package LIMITED WITH POWERBAND AUDIO PACKAGE in Racine, WI

Used 2024 Indian Motorcycle Cruiser

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

Stock # I422549

<p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">All the same features of the Chieftain Dark Horse in a class package of premium meta

Indian Motorcycle of Racine

2019 Indian Motorcycle® Chieftain® Classic Deep Water Metallic / Dirt Track Ta CLASSIC in Temple, TX

Used 2019 Indian Motorcycle® Cruiser

Chieftain® Classic Deep Water Metallic / Dirt Track Ta CLASSIC

Stock # U381112

<p>Experience the open road on a reliable cruiser. This Used 2019 Indian Motorcycle® Chieftain® Classic Deep Water Metallic / Dirt Track Tan offers cl

Bell County Motoworks

2018 Indian Motorcycle Chieftain in Bettendorf, IA

Used 2018 Indian Motorcycle Touring

<p style="margin-bottom: 1em;">Here is a 2018 Indian Chieftain, with only 31,839 Miles on it!!!! The 2018 Indian Chieftain is a powerful, stylish bag

Brennys Motorcycle Clinic

2017 Indian Motorcycle Chieftain® in Hollister, CA

Used 2017 Indian Motorcycle Cruiser

<p>Followers Need Not Apply</p><p style="margin-bottom: 1em;">No bike can make you a leader. But this one certainly sends a message. Powered by our fo

Hollister Powersports

2018 Indian CHIEFTAIN LIMITED LIMITED in Greenville, SC

Used 2018 Indian Cruiser

CHIEFTAIN LIMITED LIMITED

This is a n Amazing 2018 Indian Chieftain Limited, powered by a 111 cubic-inch (1,811 cc) Thunder Stroke 111 V-twin engine. It is in Mint condition (n

2021 Indian Motorcycle Chieftain® Limited LIMITED in Fredericksburg, VA

Used 2021 Indian Motorcycle Cruiser

Chieftain® Limited LIMITED

Old Dominion Harley Davidson

Fredericksburg, VA

2026 Indian Motorcycle® CHIEFTAIN PP DH 112, BLK/BLK CRYSTAL, 49ST BASE in Tampa, FL

New 2026 Indian Motorcycle® Custom

CHIEFTAIN PP DH 112, BLK/BLK CRYSTAL, 49ST BASE

2026 Indian Motorcycle® CHIEFTAIN PP DH 112, BLK/BLK CRYSTAL, 49ST,

Bert’s Buccaneer Indian Motorcycle

2022 Indian CHIEFTAIN DARK HORSE, RUBY SMOKE, 49ST DARK HORSE in Colorado Springs, CO

Used 2022 Indian Cruiser

CHIEFTAIN DARK HORSE, RUBY SMOKE, 49ST DARK HORSE

Stock # P405009

<p>Experience the open road with style on this striking cruiser. This used 2022 Indian CHIEFTAIN DARK HORSE, RUBY SMOKE, 49ST motorcycle is designed f

Pikes Peak Indian Motorcycle

Colorado Springs, CO

2026 Indian Motorcycle Chieftain® Dark Horse® with PowerBand Audio Package DARK HORSE WITH POWERBAND AUDIO PACKAGE in Bala Cynwyd, PA

New 2026 Indian Motorcycle Cruiser

Chieftain® Dark Horse® with PowerBand Audio Package DARK HORSE WITH POWERBAND AUDIO PACKAGE

<p style="margin-bottom: 1em;">Powered by the air-cooled Thunderstroke, Chieftain is comfortable, compact, and agile - ready to carve turns or take a

Quaker City Motorsports

Bala Cynwyd, PA

2026 Indian Motorcycle Chieftain® Dark Horse® DARK HORSE in Union City, TN

New 2026 Indian Motorcycle Cruiser

Chieftain® Dark Horse® DARK HORSE

<p style="margin-bottom: 1em;">Powered by the air-cooled Thunderstroke, Chieftain is comfortable, compact, and agile - ready to carve turns or take a

Interstate 69 Motorsports

2021 Indian Motorcycle Chieftain® Limited LIMITED in Massillon, OH

Used 2021 Indian Motorcycle Cruiser

Chieftain® Limited LIMITED

Stock # UM26218

<p>6 MONTH MECHANICAL WARRANTY INCLUDED!</p>

J & J Motors Inc.

2019 Indian Motorcycle® Chieftain Dark Horse® White Smoke DARK HORSE in Knoxville, TN

Used 2019 Indian Motorcycle® Cruiser

Chieftain Dark Horse® White Smoke DARK HORSE

2019 Indian Motorcycle® Chieftain Dark Horse® White Smoke, INDIAN STAGE 2 CAMS, INDIAN INTAKE UPGRADE, AND RINEHART EXHAUST. UPGRADED INDIAN FLOORBOAR

Indian Triumph of Knoxville

2018 Indian CHIEFTAIN DARK HORSE DARK HORSE in Tulsa, OK

Used 2018 Indian Cruiser

CHIEFTAIN DARK HORSE DARK HORSE

<p>Unveil the ultimate blend of heritage and modernity with the 2018 Indian Chieftain Dark Horse, a masterpiece in motorcycle craftsmanship. This stri

Synergy Motorworks

2017 Indian CHIEFTAIN SMOKE BASE in Sioux Falls, SD

Used 2017 Indian Touring

CHIEFTAIN SMOKE BASE

<p>Experience the open road with the 2017 Indian Chieftain Smoke, a touring motorcycle designed for adventure. This used Indian Chieftain Smoke combin

Power Brokers Inc

Sioux Falls, SD

2018 Indian Motorcycle Chieftain® Limited ABS LIMITED in Fredericksburg, VA

Used 2018 Indian Motorcycle Cruiser

Chieftain® Limited ABS LIMITED

<p>Build your legend as the leader of the pack.</p><p style="margin-bottom: 1em;"><strong>Certified Pre-Owned Motorcycle Includes a 30 Day / 1500 Mile

Classic Iron Inc

Fredericksburg, VA

2026 Indian Motorcycle CHIEFTAIN DARK HORSE DARK HORSE in Raleigh, NC

New 2026 Indian Motorcycle Cruiser

CHIEFTAIN DARK HORSE DARK HORSE

Stock # NI-3440754

<p>Unleash the road with the 2026 Indian Motorcycle Chieftain Dark Horse. This new cruiser combines style and power for an unforgettable ride. It’s pe

2024 Indian CHEIFTAN in Santa Clarita, CA

Used 2024 Indian Cruiser

2024 Indian CHEIFTAN, <b>Displacement:</b> 111 cu. in. (1811 cc)<br> <b>Engine Type:</b> V Twin<br> <b>Bore and Stroke:</b> Bore: 3.98 in. (101 mm); S

Ken & Joe's Motorsports

Santa Clarita, CA

2026 Indian Motorcycle Chieftain Dark Horse DARK HORSE in Dulles, VA

New 2026 Indian Motorcycle Cruiser

Chieftain Dark Horse DARK HORSE

Stock # I022644

2026 Indian Motorcycle Chieftain Dark Horse, <p>Motorcycles of Dulles, Northern Virginia's exclusive BMW, Triumph, Indian, Royal Enfield, MV Agusta, a

Motorcycles of Dulles

2026 Indian Motorcycle® Chieftain® Limited Sunset Red Metallic LIMITED in Hagerstown, MD

New 2026 Indian Motorcycle® Touring

Chieftain® Limited Sunset Red Metallic LIMITED

2026 Indian Motorcycle® Chieftain® Limited Sunset Red Metallic, Total Price: Excludes State Tax, Tag, Title and Registration<br /> <br /> 2026 Indian

Twigg Cycles, Inc

2019 Indian CHIEFTAIN DARK HORSE DARK HORSE in Fayetteville, NC

Used 2019 Indian Cruiser

CHIEFTAIN DARK HORSE DARK HORSE

Stock # F379715

2019 INDIAN CHIEFTAIN DARK HORSE, Riding the 2019 Indian Chieftain Dark Horse feels like commanding the road with every twist of the throttle. The Thu

Fayetteville, NC

2017 Indian Motorcycle® Chieftain® Thunder Black Pearl in Fayetteville, NC

Used 2017 Indian Motorcycle® Touring

Chieftain® Thunder Black Pearl

Stock # U344898

2017 Indian Motorcycle® Chieftain® Thunder Black Pearl, Parts Included: Slip-On Exhaust, Taller Windscreen, Highway Pegs. Great Deals, easy financing,

Baker American Cycles

Fayetteville, NC

2023 Indian Motorcycle Chieftain Dark Horse DARK HORSE in Greensboro, NC

Used 2023 Indian Motorcycle Cruiser

Chieftain Dark Horse DARK HORSE

Stock # TP3414152

<p>Experience the road like never before on the 2023 Indian Motorcycle Chieftain Dark Horse. This used cruiser offers an impressive blend of style and

Motorcycles of Greensboro

2024 Indian Motorcycle CHIEFTAN DARK HORSE WHITE METALLIC SMOKE DARK HORSE in Chambersburg, PA

New 2024 Indian Motorcycle Cruiser

CHIEFTAN DARK HORSE WHITE METALLIC SMOKE DARK HORSE

2024 Indian Motorcycle CHIEFTAN DARK HORSE WHITE METALLIC SMOKE, Pre-Owned 2024 Indian Chieftain Dark Horse in Ghost White Metallic Smoke<br><br>Pre-O

Chambersburg, PA

2026 Indian Motorcycle Chieftain® Limited LIMITED in Saint Clairsville, OH

New 2026 Indian Motorcycle Cruiser

Chieftain® Limited LIMITED

Stock # B8T3444281

Powered by the legendary Thunderstroke 116 giving you more power, more technology, and premium chrome finishes.

North Star Polaris, LLC

Saint Clairsville, OH

2026 Indian Motorcycle® Chieftain® Dark Horse® w/PowerBand Audio Black Smoke DARK HORSE WITH POWERBAND AUDIO PACKAGE in North Canton, OH

New 2026 Indian Motorcycle® Cruiser

Chieftain® Dark Horse® w/PowerBand Audio Black Smoke DARK HORSE WITH POWERBAND AUDIO PACKAGE

Stock # 1013371

2026 Indian Motorcycle® Chieftain® Dark Horse® w/PowerBand Audio Black Smoke, Shipping 7/24. Ask about financing as low as 4.99% for 36 months with $0

Bair's Powersports & Bair's Indian Motorcycle

North Canton, OH

2026 Indian Chieftain Limited LIMITED in Westerville, OH

New 2026 Indian Touring

Chieftain Limited LIMITED

Stock # T3443360

2026 Indian Chieftain Limited, - Ready to ride? Call/text (614) 212-7888 or Request More Information from the Shopping Tools Menu -<br><br>$29749 MSRP

Pony Powersports Group, LLC

Westerville, OH

2026 Indian Motorcycle® Chieftain® Dark Horse® w/PowerBand Audio Deep Blue Me DARK HORSE in Sturgis, SD

New 2026 Indian Motorcycle® Cruiser

Chieftain® Dark Horse® w/PowerBand Audio Deep Blue Me DARK HORSE

2026 Indian Motorcycle® Chieftain® Dark Horse® w/PowerBand Audio Deep Blue Metallic, 2026 Indian Motorcycle® Chieftain® Dark Horse® w/PowerBand Audio

Indian Motorcycle Sturgis

2026 Indian Motorcycle Chieftain Dark Horse with Power Band Audio DARK HORSE in Norman, OK

New 2026 Indian Motorcycle Touring

Chieftain Dark Horse with Power Band Audio DARK HORSE

<p>STYLED WITH AN EDGE</p><p style="margin-bottom: 1em;">Premium Black Finishes, A Sleek Fairing, Saddlebags, and a Gunfighter Style Seat deliver a st

Sooner Indian Motorcycles

2026 Indian CHIEFTAIN DARK HORSE DARK HORSE in Charleston, IL

New 2026 Indian Standard

CHIEFTAIN DARK HORSE DARK HORSE

Stock # I440749

2026 Indian CHIEFTAIN DARK HORSE, <b>Displacement:</b> 116 cu. in. (1890 cc)<br> <b>Engine Type:</b> V Twin<br> <b>Bore and Stroke:</b> Bore: 4.06 in.

Owen Motor Sports

2026 Indian Chieftain Dark Horse Deep Blue Metallic DARK HORSE in Tucson, AZ

New 2026 Indian Cruiser

Chieftain Dark Horse Deep Blue Metallic DARK HORSE

Stock # IN445080

2026 Indian Chieftain Dark Horse Deep Blue Metallic, 4.99% FINANCING AVAILABLE! Shop our 44,000 square foot indoor showroom or call our Web Sales team

RideNow - Tucson East

2026 Indian CHIEFTAIN PP DARK HORSE, BLACK SMOKE, 49ST DARK HORSE in Murfreesboro, TN

New 2026 Indian Standard

CHIEFTAIN PP DARK HORSE, BLACK SMOKE, 49ST DARK HORSE

2026 Indian CHIEFTAIN PP DARK HORSE, BLACK SMOKE, 49ST, 2026 Indian CHIEFTAIN PP DARK HORSE, BLACK SMOKE, 49ST

Sloans Motorcycle & ATV

Murfreesboro, TN

Available Years

2026 Indian CHIEFTAIN - 94 motorcycles
2019 Indian CHIEFTAIN - 69 motorcycles
2024 Indian CHIEFTAIN - 63 motorcycles
2018 Indian CHIEFTAIN - 59 motorcycles

2025 Indian CHIEFTAIN - 52 motorcycles
2017 Indian CHIEFTAIN - 45 motorcycles
2022 Indian CHIEFTAIN - 38 motorcycles
2020 Indian CHIEFTAIN - 36 motorcycles

2021 Indian CHIEFTAIN - 33 motorcycles
2023 Indian CHIEFTAIN - 33 motorcycles

Top Available Cities with Inventory

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