Used Convertibles for Sale near Chicago, IL

1,519 results

Chicago, IL

Sort by:

2013 BMW Z4

sDrive28i Roadster RWD

53,288 miles

$17,500

Good Deal

Lemont, IL

20 mi away

Year:: 2013
Make:: BMW
Model:: Z4
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 240 hp 2L I4
Exterior color:: Black
Combined gas mileage:: 27 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 53,288
Stock number:: 17676
VIN:: WBALL5C51DJ104762

Sponsored

2023 Ford Mustang

EcoBoost Premium Convertible RWD

59,294 miles

$23,000

Fair Deal

Chicago, IL

9 mi away

Year:: 2023
Make:: Ford
Model:: Mustang
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 310 hp 2.3L I4
Exterior color:: Gray Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black (Ebony)
Transmission:: Automatic
Mileage:: 59,294
Stock number:: P22646
VIN:: 1FATP8UH3P5103455

Sponsored

2014 Mercedes-Benz E-Class

E 350 Cabriolet

45,285 miles

$19,991

Fair Deal

Highland Park, IL

24 mi away

Year:: 2014
Make:: Mercedes-Benz
Model:: E-Class
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 302 hp 3.5L V6
Exterior color:: Black
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 45,285
Stock number:: P260112A
VIN:: WDDKK5KFXEF251457

Sponsored

2005 Chrysler Crossfire

Limited Roadster RWD

67,296 miles

$7,871

Good Deal

North Aurora, IL

39 mi away

Year:: 2005
Make:: Chrysler
Model:: Crossfire
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 215 hp 3.2L V6
Exterior color:: Black Clearcoat/Black Cloth Top
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Dark Gray/Med Gray
Transmission:: 5-Speed Automatic
Mileage:: 67,296
Stock number:: 52393A1
VIN:: 1C3AN65LX5X043839

2008 Volkswagen Beetle

2.5 Convertible

124,929 miles

$5,995

Good Deal

Portage, IN

31 mi away

Year:: 2008
Make:: Volkswagen
Model:: Beetle
Body type:: Convertible
Exterior color:: Red
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 124,929
Stock number:: 5779
VIN:: 3VWRF31Y68M415969

2008 Chrysler Sebring

Limited Convertible FWD

104,047 miles

$4,950

Good Deal

Maywood, IL

11 mi away

Year:: 2008
Make:: Chrysler
Model:: Sebring
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Front-Wheel Drive
Engine:: 235 hp 3.5L V6
Exterior color:: Brilliant Black Crystal Pearlcoat
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: 6-Speed Automatic
Mileage:: 104,047
Stock number:: 2281
VIN:: 1C3LC65M18N637923

Preparing for a close up...

Photos coming soon

2004 Ford Mustang

Deluxe Convertible RWD

145,000 miles

$4,950

Good Deal

Maywood, IL

11 mi away

Year:: 2004
Make:: Ford
Model:: Mustang
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 193 hp 3.9L V6
Exterior color:: White
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 4-Speed Automatic
Mileage:: 145,000
Stock number:: 2054
VIN:: 1FAFP44614F240940

Preparing for a close up...

Photos coming soon

2014 Mercedes-Benz SLK

250

65,791 miles

$14,475

Great Deal

Highland, IN

25 mi away

Year:: 2014
Make:: Mercedes-Benz
Model:: SLK
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 201 hp 1.8L I4
Exterior color:: Silver
Combined gas mileage:: 28 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: 7-Speed Automatic
Mileage:: 65,791
Stock number:: ML8747
VIN:: WDDPK4HAXEF084321

Preparing for a close up...

Photos coming soon

2015 Jaguar XK-Series

XKR Convertible RWD

27,314 miles

$37,991

Great Deal

Crystal Lake, IL

42 mi away

Year:: 2015
Make:: Jaguar
Model:: XK-Series
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 510 hp 5L V8
Exterior color:: Black Amethyst Metallic
Fuel type:: Gasoline
Interior color:: Black (Warm Charcoal)
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 27,314
Stock number:: P6801A
VIN:: SAJWA4EC4FMB55786

Preparing for a close up...

Photos coming soon

2019 Buick Cascada

Sport Touring FWD

68,357 miles

$15,999

Great Deal

Lincolnwood, IL

10 mi away

Year:: 2019
Make:: Buick
Model:: Cascada
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Front-Wheel Drive
Engine:: 1.6L I4
Exterior color:: Black (Ebony Twilight Metallic)
Combined gas mileage:: 25 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 68,357
Stock number:: PA8276
VIN:: W04WJ3N50KG359835

Preparing for a close up...

Photos coming soon

2022 Mercedes-Benz SL-Class

AMG SL 63 4MATIC

4,754 miles

$108,750

Great Deal

Certified Pre-Owned

Lincolnwood, IL

11 mi away

Year:: 2022
Make:: Mercedes-Benz
Model:: SL-Class
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 577 hp 4L V8
Exterior color:: Obsidian Black Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Red Pepper/Black
Transmission:: 9-Speed Automatic
Mileage:: 4,754
Stock number:: PP2416
VIN:: W1KVK8BBXNF001602

Preparing for a close up...

Photos coming soon

2017 Mercedes-Benz SLC

AMG SLC 43

19,692 miles

$32,500

Good Deal

Barrington, IL

31 mi away

Year:: 2017
Make:: Mercedes-Benz
Model:: SLC
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 362 hp 3L V6
Exterior color:: Obsidian Black Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 9-Speed Automatic
Mileage:: 19,692
Stock number:: PPR4112
VIN:: WDDPK6GA4HF128122

Preparing for a close up...

Photos coming soon

2014 Volkswagen Beetle

R-Line Convertible

70,064 miles

$13,991

Great Deal

Crystal Lake, IL

42 mi away

Year:: 2014
Make:: Volkswagen
Model:: Beetle
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Front-Wheel Drive
Engine:: 210 hp 2L I4
Exterior color:: Platinum Gray Metallic
Combined gas mileage:: 26 MPG
Fuel type:: Gasoline
Interior color:: Titan Black
Transmission:: 6-Speed Dual Clutch
Mileage:: 70,064
Stock number:: PV10198
VIN:: 3VW7T7AT7EM801601

Preparing for a close up...

Photos coming soon

2024 Chevrolet Corvette

Stingray 1LT Convertible RWD

9,670 miles

$67,988

Fair Deal

Glenview, IL

15 mi away

Year:: 2024
Make:: Chevrolet
Model:: Corvette
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 6.2L V8
Exterior color:: Gray
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 9,670
Stock number:: P4381
VIN:: 1G1YA3D49R5118071

Preparing for a close up...

Photos coming soon

2004 Porsche 911

Carrera Cabriolet RWD

74,354 miles

$25,980

Good Deal

Waukegan, IL

35 mi away

Year:: 2004
Make:: Porsche
Model:: 911
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 315 hp 3.6L H6
Exterior color:: Arctic Silver Metallic
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Manual
Mileage:: 74,354
Stock number:: 8586
VIN:: WP0CA29984S653371

Preparing for a close up...

Photos coming soon

2017 Audi A5

2.0T quattro Sport Cabriolet AWD

25,721 miles

$22,587

Good Deal

Highland Park, IL

24 mi away

Year:: 2017
Make:: Audi
Model:: A5
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 220 hp 2L I4 Flex Fuel Vehicle
Exterior color:: Gray
Combined gas mileage:: 25 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Black
Transmission:: Automatic
Mileage:: 25,721
Stock number:: A260089A
VIN:: WAUD2AFH6HN002703

Preparing for a close up...

Photos coming soon

2007 Chrysler Crossfire

Roadster RWD

46,013 miles

$10,500

Good Deal

Naperville, IL

27 mi away

Year:: 2007
Make:: Chrysler
Model:: Crossfire
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 215 hp 3.2L V6
Exterior color:: Black
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Manual
Mileage:: 46,013
Stock number:: 0198
VIN:: 1C3LN59L47X071250

Preparing for a close up...

Photos coming soon

2018 Mazda MX-5 Miata

Grand Touring RWD

24,596 miles

$19,698

Great Deal

Countryside, IL

15 mi away

Year:: 2018
Make:: Mazda
Model:: MX-5 Miata
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 155 hp 2L I4
Exterior color:: Jet Black Mica
Combined gas mileage:: 29 MPG
Fuel type:: Gasoline
Interior color:: Black W/Red Stitching
Transmission:: 6-Speed Manual
Mileage:: 24,596
Stock number:: CS38439A
VIN:: JM1NDAD72J0203173

Preparing for a close up...

Photos coming soon

2015 Maserati GranTurismo

Convertible

75,293 miles

$25,250

Fair Deal

Palos Hills, IL

16 mi away

Year:: 2015
Make:: Maserati
Model:: GranTurismo
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 444 hp 4.7L V8
Exterior color:: White
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Brown (BEIGE)
Transmission:: Automatic
Mileage:: 75,293
Stock number:: PH1750
VIN:: ZAM45MMA2F0157045

Preparing for a close up...

Photos coming soon

2009 Porsche 911

Carrera Cabriolet RWD

26,551 miles

$57,997

Fair Deal

Batavia, IL

33 mi away

Year:: 2009
Make:: Porsche
Model:: 911
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 345 hp 3.6L H6
Exterior color:: Basalt Black Metallic
Fuel type:: Gasoline
Interior color:: Brown (Sand Beige)
Transmission:: 7-Speed Automatic
Mileage:: 26,551
Stock number:: 1318
VIN:: WP0CA29939S740487

Preparing for a close up...

Photos coming soon

2005 Audi TT

1.8T quattro Roadster AWD

76,814 miles

$8,995

Great Deal

McHenry, IL

45 mi away

Year:: 2005
Make:: Audi
Model:: TT
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 225 hp 1.8L I4
Exterior color:: Silver
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Manual
Mileage:: 76,814
Stock number:: C302
VIN:: TRUUT28N751002940

Preparing for a close up...

Photos coming soon

2017 Mercedes-Benz SL-Class

SL 550 RWD

23,525 miles

$47,995

Good Deal

Chicago Heights, IL

26 mi away

Year:: 2017
Make:: Mercedes-Benz
Model:: SL-Class
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 449 hp 4.7L V8
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Transmission:: 9-Speed Automatic
Mileage:: 23,525
Stock number:: Consignment
VIN:: WDDJK7DA7HF043310

Preparing for a close up...

Photos coming soon

2022 BMW M4

Competition xDrive Convertible AWD

20,296 miles

$63,995

Good Deal

Joliet, IL

34 mi away

Year:: 2022
Make:: BMW
Model:: M4
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 503 hp 3L I6
Exterior color:: Frozen Brilliant White Metallic
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Ivory White
Transmission:: 8-Speed Automatic
Mileage:: 20,296
Stock number:: 7991-TR
VIN:: WBS33BA07NCJ71910

Sponsored

Reviews

4.6 Overall rating

(36,558 reviews)

Kevin B

5.0

Reviewed a 2021 Porsche 911 on Jan 16, 2024

Outstanding. There are so many words that have already been written to describe the singular driving experience of the Porsche 911, but none that can actually convey that experience. Having bought my first Porsche 911, I finally get it. What a vehicle.

Thomas J S

5.0

Reviewed a 2021 Bentley Continental GTC on Nov 05, 2024

Car was exactly as advertised. Great condition and low mileage.

Mark T

5.0

Reviewed a 2014 Audi RS 5 on Oct 26, 2024

This is an amazing car! It does everything well. It’s fast it corners well and you can drive it across the country if you want.

Antonio B

5.0

Reviewed a 2017 Mercedes-Benz SL-Class on Jul 05, 2024

The SL450 is missing nothing. Its gorgeous and an incredible GT.

Brady G

5.0

Reviewed a 2003 Honda Roadster on May 05, 2024

The absolute most fun you can have for the money.

Shop by Price

Shop By City

Convertibles by Make

Popular Convertibles

Shop by Fuel Type

Used Electric Convertibles for Sale