NEW HARLEY-DAVIDSON® MOTORCYCLE INVENTORY

Explore new 2025 & 2026 Harley-Davidson® models for sale at Windy City Harley-Davidson® in Libertyville, IL

Find your next new motorcycle when you work with the experts at Windy City Harley-Davidson^®! We offer a huge selection of hundreds of new bikes for sale, so we're sure to have something in stock to fit your riding needs!

Why Buy From Us?

Anyone can sell you a motorcycle. What sets us apart is what happens after. We believe in treating people like family, not numbers, and making sure every rider feels supported long after they leave the showroom. From service and parts to events and community, we’re here for the long haul — because your experience shouldn’t end when the sale does.

ALL NEW PRE-OWNED

ALL

NEW

PRE-OWNED

Showing 181 - 192 of 467 results

page_infoFilters

Showing 181 - 192 of 467 results

Clear all filters

Motorcycles

Harley-Davidson®

Adventure Touring

Cruiser

CVO

Dyna

Grand American Touring

S-Series

Softail

Sportster

Street

Trike

V-Rod

1200 Custom

Breakout

CVO

Cvo Road King

Cvo Ultra Classic Electra Glide

Electra Glide

Electra Glide Classic

Fat Bob

Fat Boy

Fat Boy Lo

FLHR103

FLHTCU103

FLHX103

FLTCU

FLTRU103

Forty-Eight

Freewheeler

FXDWG

FXSTDSE2

Harley-Davidson Street

Heritage

Iron

Low Rider

Night Rod

Night Train®

Nightster

Pan America

Road Glide

Road King

Rocker

Softail Deluxe

Softail Deuce

Softail Slim

Softail Standard

Softail^® Deluxe

Softail® Deluxe

Sport Glide

Sportster

Sportster 1200 Custom

Sportster 1200 Custom Hd1 Base

Sportster 883

Springer

Street Bob

Street Glide

Street Glide Ultra

Super Glide

SuperLow

Switchback

Tri Glide

Tri Glide Ultra Classic

Ultra Limited

Wide Glide

105th Anniversary Copper Pearl & Vivid Black

2T RED

Alpine Green

Alpine Green / Vivid Black

Atlas Silver Metallic

Auburn Sunglo & Black Hole with Rich Bourbon

Baja Orange

BIG BLUE PEARL

Big Blue Pearl/Vivid Black

BIG BLUE/V BLK W/ PINSTRIPE

BIL BLU/BIL GRY

BIL SLVR/V BLK W/PINSTRIPE

Billet Silver

Billiard Blue

BILLIARD BURGANDY

Billiard Gray

Billiard Gray w/Cast Wheels

Billiard Red

BLACK

Black Cherry

BLACK CHERRY W/PINSTRIPE

Black Denim

BLACK FLAME CUST

Black Forest

Black Jack Metallic

Black Licorice with Midnight Cobalt Flames

BLACK PEARL

Black Quartz

Black Stardust Fade

BLACK W/ PINSTRIPE

BLACK W/PINSTRIPE

BLACK/BLUE

BLACKND CAYENNE W/ PINSTRIP

BLK

BLK CHERRY/PEWTER W/PINSTRI

BLK DEN

BLK LIC/MDNTCBT W/PINSTRIPE

BLK/PEWTER PRL

BLU/BLK

BLUE

Blue Burst

Blue Streak

BLUE/BLK

BLUE/SILVER

Bonneville Salt Denim

BRACUDA SLV DNM W/PINSTRIPE

Bright Billiard Blue

Brilliant Red

Brilliant Silver Pearl

Bronze Armor

BROWN\BLACK

BRSLVDNM/BLKDNM W/PINSTRIPE

BRT BILIARD BLU

Carbon Blue

Centerline w/Cast Wheels

Charcoal Satin

CHR DNM/BLK DNM W/PINSTRIPE

CHRM YELLOW PRL

CHRM YELLOW PRL W/ PINSTRIP

CITRUS/GUNSTOCK W/ PINSTRIP

COBALT/BLACK

COBALT/SILVER

COBALT/SILVER W/PINSTRIPE

COOL BLUE DLX

COOL BLUE/V BLK

COPPER/BLACK

CPR/BLK

CRB CRY/PTM FLM

CRIMSON RED

Crushed Ice Denim

Crushed Ice Pearl

CRY COP/PNYX

CUSTOM

Custom Colour Cosmic Blue Pearl

DARK BLUE DENIM

Dark Blue Pearl

Dark Platinum w/Pinstripe

DAYTONA BLUE

Deadwood Green/Vivid Black - Black Finish

DEEP COBALT

Deep Jade Pearl

DK/LT ROOT BEER

Electric Blue

Ember Red Sunglo

EMBR RED SUNGLO

EMBR RED SUNGLO W/ PINSTRIP

EMBR RED/MERLOT W/ PINSTRIP

EMERALD GREEN/GREEN W/PINSTRIPE

Envious Green Fade

Exclusive - Dark Blue - Peace Officer

FLM BLUE/SILVER

FLM BLUE/V BLK

G WHT/COBALT W/PINSTRIPE

GAUNT GRY MTLIC

Gauntlet Gray Metallic

GLACIER WHITE

GOLDEN BLACK PEARL

Gray Haze

Gunship Gray

Hard Candy Custom™ Mystic Purple Flake

Hard Candy Gold Flake

Hard Candy Hot Rod Red Flake

HC SHATTEREDFLK

HCCHROMEFLAKE

Heirloom Red Fade

INDGRYDNM/BLKDM W/PINSTRIPE

INDGRYDNM/BLKDN W/PINSTRIPE

INDSTRL GRY DNM

INDSTRL GRYDNM

Industrial Gray Denim/Black Denim

Industrial Yellow

Iron Horse Metallic

Iron Horse Metallic - Black Finish

Iron Horse Metallic w/Cast Wheels

Iron Horse Metallic w/Laced Wheels

Kinetic Green

Legend Blue Denim

LT/DK ROOT BEER

LUXURY BLUE/ICE W/STRIPES

MAROON

MDNGHT FIRSTORM

MDNTBLU/BARSLVR W/PINSTRIPE

MERLOT

MERLOT SUNGLO

MERLOT/BLK

Midnight Blue

Midnight Crimson

Midnight Crimson/Vivid Black

Midnight Firestorm - Black Finish

MIDNIGHT PEARL

MIDNIGHT PEARL W/ PINSTRIPE

MIDNIGHT PEARL/

MIDNIGHT/SLVER

Mineral Green Metallic

MIRAGE ORANGE

Moonlight Blue & Deep Sea Blue

Morocco Gold Pearl

MOROCCO GOLD W/ PINSTRIPE

MYS RED/CAYENNE W/ PINSTRIP

MYSTERIOUS RED W/ PINSTRIPE

Mystic Shift - Black Finish

Olive Gold

PAC BLUE/BLK W/PINSTRIPE

PEWTER PRL

Prospect Gold - Black Finish

Purple Abyss Denim - Black Finish

Raven Metallic

RED PEARL

Red Pepper & Magnetic Gray with Black Hole

Red Rock

RED/BLACK

RED/BLACK PEARL

RED/GRAY

Redline Red

Redline Red/Vivid Black (Black Finish w/Cast Wheels)

Reef Blue/Vivid Black - Black Finish

River Rock Gray

ROOTBEER

RVR RCK GRY/BLK W/PINSTRIPE

SAND CAMO DENIM

Scorched Orange/Black Denim

Sharkskin Blue - Black Finish

SIERRA RED

Silver

Silver Fortune

Silver Fortune/Black Tempest

SILVER/BLACK

SINISTER BLUE PRL/DIAMOND I

SMKYGRY/BLKHOLE W/PINSTRIPE

Snake Venom

ST SLV/TW BLUE

Starfire Black/Atomic Red with Contrast Chrome Aggressor Wheels

Stiletto Red

Stone Washed White Pearl

Superior Blue

Tahitian Teal

Twisted Cherry

Twisted Cherry/Silver Fortune

Two-Tone Amber Whiskey/Vivid Black

Two-Tone Anniversary Diamond Dust/Obsidian with Palladium Graphics

Two-Tone Black Hills Gold/Black Quartz

Two-Tone Mysterious Red Sunglo/Velocity Red Sunglo

UNKNOWN

V BLK/BLK ICE

V BLK/BRIL SLVR

Velocity Red Sunglo

Vivid Black

Vivid Black - Black Finish

Vivid Black w/Laced Wheels

VIVID BLACK W/STRIPE

Vivid Black with Orange Pin Stripe Wheels

VIVID BLACK/BRILLIANT SILVE

Whiskey Fire

Whiskey Fire / Vivid Black

WHITE

WHITE HOT PEARL W/

White Onyx Pearl

White Onyx Pearl Black Trim

White Sand Pearl

WHT GOLD/COBALT W/PINSTRIPE

Wicked Red

WINEBERRY/CHARCOAL

WKDRED/TWTDCHRY

YELLO PRL/V BLK W/ PINSTRIP

Price from

Price to

Year from 2026 Year from 2025 Year from 2024 Year from 2023 Year from 2022 Year from 2021 Year from 2020 Year from 2019 Year from 2018 Year from 2017 Year from 2016 Year from 2015 Year from 2014 Year from 2013 Year from 2012 Year from 2011 Year from 2010 Year from 2009 Year from 2008 Year from 2007 Year from 2006 Year from 2005 Year from 2004 Year from 2003 Year from 2002 Year from 2001 Year from 2000 Year from 1999 Year from 1998 Year from 1997 Year from 1996 Year from 1995 Year from 1994 Year from 1993 Year from 1992 Year from 1991 Year from 1990 Year from 1989 Year from 1988 Year from 1987 Year from 1986

Year to 2026 Year to 2025 Year to 2024 Year to 2023 Year to 2022 Year to 2021 Year to 2020 Year to 2019 Year to 2018 Year to 2017 Year to 2016 Year to 2015 Year to 2014 Year to 2013 Year to 2012 Year to 2011 Year to 2010 Year to 2009 Year to 2008 Year to 2007 Year to 2006 Year to 2005 Year to 2004 Year to 2003 Year to 2002 Year to 2001 Year to 2000 Year to 1999 Year to 1998 Year to 1997 Year to 1996 Year to 1995 Year to 1994 Year to 1993 Year to 1992 Year to 1991 Year to 1990 Year to 1989 Year to 1988 Year to 1987 Year to 1986

Length from

Length to

Mileage < 100 mi Mileage < 500 mi Mileage < 1000 mi Mileage < 3000 mi Mileage < 5000 mi Mileage < 10000 mi Mileage < 15000 mi Mileage < 20000 mi Mileage < 25000 mi Mileage < 30000 mi Mileage < 35000 mi Mileage < 40000 mi Mileage < 45000 mi Mileage < 50000 mi Mileage < 55000 mi Mileage < 60000 mi Mileage < 65000 mi Mileage < 70000 mi Mileage < 75000 mi Mileage < 80000 mi Mileage < 85000 mi Mileage < 90000 mi Mileage < 95000 mi Mileage < 100000 mi Mileage < 105000 mi Mileage < 110000 mi Mileage < 115000 mi Mileage < 120000 mi Mileage < 125000 mi Mileage < 130000 mi Mileage < 135000 mi Mileage < 140000 mi Mileage < 145000 mi Mileage < 150000 mi Mileage < 155000 mi Mileage < 160000 mi Mileage < 165000 mi Mileage < 170000 mi Mileage < 175000 mi Mileage < 180000 mi Mileage < 185000 mi Mileage < 190000 mi Mileage < 195000 mi Mileage < 200000 mi

Chicago Harley-Davidson®

Illinois Harley-Davidson®

Starved Rock Harley-Davidson

Windy City Harley-Davidson®

Woodstock Harley-Davidson®

Other

Petrol

Other

Featured

Custom

Sold as seen

Manufacturer certified

Dealer certified

Cal spec

In Stock

New arrivals

Cruiser

Touring

Sport

Off-Road

XL 883N 2019 Iron 883™ $10,694.00 $7,999.00

415124

Pre-owned

2019

1780 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD4LE214KC415124

Black Denim

Feel the purity of two wheels, a handle bar and an engine. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, the Iron 883™ model has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with …

Find out more CHECK AVAILABILITY
Harley-Davidson® Ultra Limited 2019 FLHTK INDGRYDNM/BLKDN W/PINSTRIPE $30,489.00 $16,999.00

676824

Pre-owned

2019

44253 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KEF12KB676824

INDGRYDNM/BLKDN W/PINSTRIPE

From its new Twin-Cooled™ Milwaukee-Eight® 114 (1868cc) V-Twin engine right down to its heated hand grips, the Ultra Limited has it all. Batwing fairing and splitstream air vent for optimal air flow and reduced head buffeting. All new BOOM!™ GTS infotainment system. Electronic cruise control, …

Find out more CHECK AVAILABILITY
Harley-Davidson® Ultra Limited 2019 FLHTK GRAY $18,999.00

619496

Pre-owned

2019

59405 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KEF11KB619496

Industrial Gray Denim/Black Denim

From its new Twin-Cooled™ Milwaukee-Eight® 114 (1868cc) V-Twin engine right down to its heated hand grips, the Ultra Limited has it all. Batwing fairing and splitstream air vent for optimal air flow and reduced head buffeting. All new BOOM!™ GTS infotainment system. Electronic cruise control, …

Find out more CHECK AVAILABILITY
Harley-Davidson® Road King® Special 2019 FLHRXS BNVL SALT DENIM $23,539.00 $17,499.00

645198

Pre-owned

2019

14152 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KVP14KB645198

Bonneville Salt Denim

If you want to know what ruling the road truly feels like, reach for the mini-apehanger bars on the Road King® Special and send some fuel to its new Milwaukee-Eight® 114 engine. This is top-of-the-line power and a look that will stop traffic. Blacked out, stripped down, rolling on turbine wheels. …

Find out more CHECK AVAILABILITY
Harley-Davidson® Road King® Special 2019 FLHRXS BLACK $25,289.00 $16,995.00

602309

Pre-owned

2019

19952 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KVP13KB602309

Vivid Black

If you want to know what ruling the road truly feels like, reach for the mini-apehanger bars on the Road King® Special and send some fuel to its new Milwaukee-Eight® 114 engine. This is top-of-the-line power and a look that will stop traffic. Blacked out, stripped down, rolling on turbine wheels. …

Find out more CHECK AVAILABILITY
Harley-Davidson® Road Glide® Special 2019 FLTRXS Vivid Black $29,789.00 $15,999.00

668216

Pre-owned

2019

92657 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1KTP11KB668216

Vivid Black

WELL MAINTAINED BIKE, REGULAR CUSTOMER WHO DID ALL HIS SERVICES AT THE DEALERSHIP.

Find out more CHECK AVAILABILITY
Harley-Davidson® Low Rider® 2019 FXLR BLACK $15,649.00 $12,999.00

044957

Pre-owned

2019

9984 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YNJ28KB044957

Vivid Black

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

Find out more CHECK AVAILABILITY
Harley-Davidson® Iron 883™ 2019 XL 883N BLACK $7,999.00

404670A

Pre-owned

2019

12251 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD4LE219KC404670

Black Denim

Feel the purity of two wheels, a handle bar and an engine. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, the Iron 883™ model has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with …

Find out more CHECK AVAILABILITY

Harley-Davidson® Fat Bob® 107 2019 FXFB BLACK $10,999.00

MSRP: $17,049.00

: 029281

: Pre-owned

: 2019

: 56492 mi

: Harley-Davidson®

: Woodstock Harley-Davidson®

: 1HD1YKJ23KB029281

: Black Denim

The Fat Bob® is all Harley-Davidson, but at the same time, it’s unlike any Harley® motorcycle that ever existed before. From the modern, aggressive look of its 2-1-2 upswept exhaust and tarmac-devouring fat tyres to the massive torque of the Milwaukee-Eight® engine to the ride of the Softail® frame,…

Find out more CHECK AVAILABILITY

Harley-Davidson® Electra Glide® Ultra Classic® 2019 FLHTCU MDNTBLU/BARSLVR W/PINSTRIPE $26,089.00 $15,999.00

616993

Pre-owned

2019

31441 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1FCC14KB616993

MDNTBLU/BARSLVR W/PINSTRIPE

The 2019 Electra Glide® Ultra Classic® is the essential long-haul touring machine with classical style, unsurpassed comfort, and the power of the soul-satisfying Milwaukee-Eight® 107 engine.

Find out more CHECK AVAILABILITY
Harley-Davidson® CVO™ Limited 2019 FLHTKSE AUBURN / BLACK $44,089.00 $20,999.00

951539

Pre-owned

2019

44034 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1TEH16KB951539

Auburn Sunglo & Black Hole with Rich Bourbon

The CVO™ Limited model brings an unparalleled level of class to the Grand American Touring class. It starts with the massive power of the Twin-Cooled™ Milwaukee-Eight®117 (1923cc) V-Twin engine and just keeps rolling from there. The paint is show stopping. You get 19” front and 18” rear Tomahawk …

Find out more CHECK AVAILABILITY
FXLR 2019 Low Rider® $15,649.00 $11,499.00

026109

Pre-owned

2019

6309 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YNJ27KB026109

UNKNOWN

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

Find out more CHECK AVAILABILITY