Used Convertibles for Sale near Chicago, IL

1,528 results

Chicago, IL

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2013 Mercedes-Benz SLK

250

70,834 miles

$15,549

Good Deal

Arlington Heights, IL

23 mi away

Year:: 2013
Make:: Mercedes-Benz
Model:: SLK
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 201 hp 1.8L I4
Exterior color:: Palladium Silver Metallic
Combined gas mileage:: 28 MPG
Fuel type:: Gasoline
Interior color:: Brown (Sahara Beige)
Transmission:: Automatic
Mileage:: 70,834
Stock number:: 4121
VIN:: WDDPK4HAXDF056162

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2022 Ford Mustang

EcoBoost Premium Convertible RWD

84,000 miles

$18,400

Fair Deal

Roselle, IL

26 mi away

Year:: 2022
Make:: Ford
Model:: Mustang
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 310 hp 2.3L I4
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 84,000
Stock number:: 121811
VIN:: 1FATP8UH5N5121811

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2023 Porsche 911

Turbo S Cabriolet AWD

19,477 miles

$248,991

Fair Deal

Certified Pre-Owned

Barrington, IL

31 mi away

Year:: 2023
Make:: Porsche
Model:: 911
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 640 hp 3.8L H6
Exterior color:: Guards Red
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 19,477
Stock number:: PPN4024
VIN:: WP0CD2A91PS263185

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2005 Chrysler Crossfire

Limited Roadster RWD

67,296 miles

$7,571

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

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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

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2017 Mercedes-Benz SLC

AMG SLC 43

44,533 miles

$26,388

Great Deal

St Charles, IL

34 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:: Diamond Silver Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 9-Speed Automatic
Mileage:: 44,533
Stock number:: C9337
VIN:: WDDPK6GA5HF127819

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2018 Mazda MX-5 Miata

Grand Touring RWD

24,596 miles

$19,498

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

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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

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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

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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

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2014 Mercedes-Benz SLK

250

65,791 miles

$14,575

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

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2021 Chevrolet Corvette

Stingray 3LT Convertible RWD

1,010 miles

$67,600

Great Deal

Downers Grove, IL

19 mi away

Year:: 2021
Make:: Chevrolet
Model:: Corvette
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 6.2L V8
Exterior color:: Black
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Natural
Transmission:: 8-Speed Dual Clutch
Mileage:: 1,010
Stock number:: AMD5454B
VIN:: 1G1YC3D40M5121816

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2001 Chevrolet Corvette

Convertible RWD

91,043 miles

$12,880

Great Deal

Villa Park, IL

18 mi away

Year:: 2001
Make:: Chevrolet
Model:: Corvette
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 350 hp 5.7L V8
Exterior color:: Silver
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 4-Speed Automatic
Mileage:: 91,043
VIN:: 1G1YY32G415131050

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2025 Ford Mustang

GT Premium Convertible RWD

3,152 miles

$49,995

Great Deal

Crete, IL

29 mi away

Year:: 2025
Make:: Ford
Model:: Mustang
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 480 hp 5L V8
Exterior color:: Vapor Blue
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Off White/Black
Transmission:: 6-Speed Manual
Mileage:: 3,152
Stock number:: EN115225
VIN:: 1FAGP8FF5S5115225

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2012 Chrysler 200

Limited Convertible FWD

66,703 miles

$10,000

Fair Deal

Chicago, IL

8 mi away

Year:: 2012
Make:: Chrysler
Model:: 200
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Front-Wheel Drive
Engine:: 283 hp 3.6L V6 Flex Fuel Vehicle
Exterior color:: Bright White Clearcoat
Combined gas mileage:: 24 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Black/Pearl
Transmission:: 6-Speed Automatic
Mileage:: 66,703
Stock number:: P2005A
VIN:: 1C3BCBFG0CN123003

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2013 Audi S5

3.0T quattro Prestige Cabriolet AWD

29,685 miles

$16,287

Great Deal

Highland Park, IL

24 mi away

Year:: 2013
Make:: Audi
Model:: S5
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: All-Wheel Drive
Engine:: 333 hp 3L V6
Exterior color:: Blue
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 29,685
Stock number:: A260084A
VIN:: WAUVGAFHXDN016992

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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

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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

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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

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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

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2019 Porsche 911

Carrera S Cabriolet RWD

19,016 miles

$106,999

Good Deal

Lincolnwood, IL

10 mi away

Year:: 2019
Make:: Porsche
Model:: 911
Body type:: Convertible
Doors:: 2 doors
Drivetrain:: Rear-Wheel Drive
Engine:: 420 hp 3L H6
Exterior color:: Jet Black Metallic
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 7-Speed Automatic
Mileage:: 19,016
Stock number:: PA8119A
VIN:: WP0CB2A95KS136261

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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.

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