CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Convertibles for Sale near Chesterton, IN

475 results
Chesterton, IN
2004 Mercedes-Benz SL-Class SL 55 AMG The Autobarn Mazda of Evanston

2004 Mercedes-Benz SL-Class

SL 55 AMG

14,005 miles

$34,995

Fair Deal
Evanston, IL
44 mi away
Year:
2004
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
493 hp 5.4L V8
Exterior color:
Diamond Silver Metallic
Fuel type:
Gasoline
Transmission:
5-Speed Automatic Overdrive
Mileage:
14,005
Stock number:
PM21196
VIN:
WDBSK74F24F067162

Sponsored

2020 Rolls-Royce Dawn RWD

2020 Rolls-Royce Dawn

RWD

9,275 miles

$281,888

Fair Deal
Chicago, IL
36 mi away
Year:
2020
Make:
Rolls-Royce
Model:
Dawn
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
563 hp 6.6L V12
Exterior color:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
9,275
Stock number:
P27744
VIN:
SCAXZ8C07LU118324

Sponsored

2015 Ferrari California T Roadster

2015 Ferrari California T

Roadster

15,353 miles

$129,900

Fair Deal
Westmont, IL
50 mi away
Year:
2015
Make:
Ferrari
Model:
California T
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
553 hp 3.9L V8
Exterior color:
Bianco Avus
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Nero
Transmission:
7-Speed Dual Clutch
Mileage:
15,353
Stock number:
15875A
VIN:
ZFF77XJA8F0208258

Sponsored

2014 Ford Mustang V6 Premium Convertible RWD

2014 Ford Mustang

V6 Premium Convertible RWD

73,434 miles

$11,997

Good Deal
Cedar Lake, IN
28 mi away
Year:
2014
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
305 hp 3.7L V6
Exterior color:
Ingot Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
CHAR BLACK TURNED MINI LEATHER
Transmission:
6-Speed Automatic
Mileage:
73,434
VIN:
1ZVBP8EM2E5262561

2013 Volkswagen Eos Komfort SULEV

2013 Volkswagen Eos

Komfort SULEV

68,630 miles

$9,850

Good Deal
Lincolnwood, IL
44 mi away
Year:
2013
Make:
Volkswagen
Model:
Eos
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
200 hp 2L I4
Exterior color:
Indium Gray
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Interior color:
Titan Black
Transmission:
6-Speed Dual Clutch
Mileage:
68,630
Stock number:
KLW2434A
VIN:
WVWBW8AH8DV005143

2017 Mercedes-Benz S-Class S 550 Convertible

2017 Mercedes-Benz S-Class

S 550 Convertible

55,551 miles

$46,991

Good Deal
Chicago, IL
36 mi away
Year:
2017
Make:
Mercedes-Benz
Model:
S-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
449 hp 4.7L V8
Exterior color:
Gray
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
55,551
Stock number:
P0009A
VIN:
WDDXK8CB2HA019326

Preparing for a close up...

Photos coming soon

2009 Chevrolet Corvette

4LT Convertible RWD

12,437 miles

$31,500

Good Deal
Niles, MI
43 mi away
Year:
2009
Make:
Chevrolet
Model:
Corvette
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
430 hp 6.2L V8
Exterior color:
Blade Silver Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
12,437
Stock number:
N13075A
VIN:
1G1YY36W195107754

Preparing for a close up...

Photos coming soon

2012 Jaguar XK-Series

XKR Convertible RWD

39,169 miles

$27,888

Great Deal
Skokie, IL
47 mi away
Year:
2012
Make:
Jaguar
Model:
XK-Series
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
510 hp 5L V8
Exterior color:
Rhodium Silver
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black (Warm Charcoal)
Transmission:
Automatic
Mileage:
39,169
Stock number:
ICC3132
VIN:
SAJWA4EC7CMB45295

Preparing for a close up...

Photos coming soon

2021 BMW 4 Series

430i Convertible RWD

27,720 miles

$33,595

Good Deal
Valparaiso, IN
11 mi away
Year:
2021
Make:
BMW
Model:
4 Series
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
255 hp 2L I4
Exterior color:
White
Combined gas mileage:
28 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
27,720
Stock number:
CDNH03610
VIN:
WBA23AT04MCH03610

Preparing for a close up...

Photos coming soon

2007 Mercedes-Benz SL-Class

SL 55 AMG

43,843 miles

$24,950

Good Deal
Stone Park, IL
47 mi away
Year:
2007
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
510 hp 5.4L V8
Exterior color:
Black
Combined gas mileage:
14 MPG
Fuel type:
Gasoline
Interior color:
Stone Leather Interior
Transmission:
5-Speed Automatic
Mileage:
43,843
Stock number:
118422
VIN:
WDBSK72F77F118422

Preparing for a close up...

Photos coming soon

2011 Ford Mustang

V6 Premium Convertible RWD

122,355 miles

$9,495

Fair Deal
Mishawaka, IN
45 mi away
Year:
2011
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
305 hp 3.7L V6
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Saddle
Transmission:
Automatic
Mileage:
122,355
Stock number:
1972
VIN:
1ZVBP8EMXB5111107

Preparing for a close up...

Photos coming soon

2019 Buick Cascada

Sport Touring FWD

68,918 miles

$15,799

Good Deal
Lincolnwood, IL
44 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:
68,918
Stock number:
PA8276
VIN:
W04WJ3N50KG359835

Preparing for a close up...

Photos coming soon

2012 Chrysler 200

S Convertible FWD

98,649 miles

$8,500

Good Deal
Oak Forest, IL
38 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:
Tungsten Metallic Clear Coat
Combined gas mileage:
24 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
98,649
Stock number:
45483A
VIN:
1C3BCBGG3CN279910

Preparing for a close up...

Photos coming soon

2018 Mercedes-Benz SL-Class

SL 450

28,685 miles

$39,900

Good Deal
Westmont, IL
50 mi away
Year:
2018
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
362 hp 3L V6
Exterior color:
Iridium Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Bengal Red/Black
Transmission:
9-Speed Automatic
Mileage:
28,685
Stock number:
PJW6697A
VIN:
WDDJK6GAXJF053275

Preparing for a close up...

Photos coming soon

2018 Mercedes-Benz C-Class

C 300 Cabriolet 4MATIC

40,719 miles

$24,791

Good Deal
Orland Park, IL
41 mi away
Year:
2018
Make:
Mercedes-Benz
Model:
C-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
All-Wheel Drive
Engine:
241 hp 2L I4
Exterior color:
Diamond White Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Porcelain Black
Transmission:
Automatic
Mileage:
40,719
Stock number:
26266A
VIN:
WDDWK4KB8JF594626

Preparing for a close up...

Photos coming soon

2014 Mercedes-Benz E-Class

E 550 Cabriolet

44,662 miles

$24,695

Fair Deal
Skokie, IL
45 mi away
Year:
2014
Make:
Mercedes-Benz
Model:
E-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
402 hp 4.7L V8
Exterior color:
Diamond White Metallic
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
7-Speed Automatic
Mileage:
44,662
Stock number:
NAC1053
VIN:
WDDKK7DF9EF257677

Preparing for a close up...

Photos coming soon

1999 Porsche Boxster

Base

55,556 miles

$12,900

Good Deal
Alsip, IL
37 mi away
Year:
1999
Make:
Porsche
Model:
Boxster
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
201 hp 2.5L H6
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
5-Speed Manual
Mileage:
55,556
Stock number:
299410
VIN:
WP0CA2980XU626715

Preparing for a close up...

Photos coming soon

2003 Mercedes-Benz SL-Class

SL 500

81,010 miles

$9,995

Good Deal
Chicago, IL
44 mi away
Year:
2003
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
302 hp 5L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Brown (Tan)
Transmission:
Automatic
Mileage:
81,010
Stock number:
A3410
VIN:
WDBSK75F63F054766

Preparing for a close up...

Photos coming soon

2009 Mercedes-Benz SL-Class

SL 550

53,067 miles

$17,523

Great Deal
Merrillville, IN
16 mi away
Year:
2009
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
382 hp 5.5L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
53,067
Stock number:
V0N147492
VIN:
WDBSK71F29F147492

Preparing for a close up...

Photos coming soon

2005 Ford Mustang

V6 Premium Convertible RWD

52,645 miles

$10,995

Great Deal
New Lenox, IL
47 mi away
Year:
2005
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
210 hp 4L V6
Exterior color:
Gray
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
52,645
Stock number:
US 3003
VIN:
1ZVFT84N855188795

Preparing for a close up...

Photos coming soon

2006 Mercedes-Benz SL-Class

SL 500

74,097 miles

$11,997

Good Deal
Frankfort, IL
42 mi away
Year:
2006
Make:
Mercedes-Benz
Model:
SL-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
302 hp 5L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Brown (TAN)
Transmission:
Automatic
Mileage:
74,097
Stock number:
10181
VIN:
WDBSK75F96F110056

Preparing for a close up...

Photos coming soon

2013 Volkswagen Beetle

Turbo Convertible

101,425 miles

$11,963

Good Deal
Demotte, IN
31 mi away
Year:
2013
Make:
Volkswagen
Model:
Beetle
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
210 hp 2L I4
Exterior color:
Pearl Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Titan Black
Transmission:
6-Speed Dual Clutch
Mileage:
101,425
Stock number:
CHY26003A
VIN:
3VW7S7AT5DM826966

Preparing for a close up...

Photos coming soon

2025 Porsche 718 Boxster

514 miles

$94,991

Fair Deal
Certified Pre-Owned
Chicago, IL
36 mi away
Year:
2025
Make:
Porsche
Model:
718 Boxster
Body type:
Convertible
Engine:
300 hp 2L H4
Exterior color:
Jet Black Metallic
Fuel type:
Gasoline
Interior color:
Black/Bordeaux Red
Transmission:
7-Speed Automatic
Mileage:
514
Stock number:
TL001685AA
VIN:
WP0CA2A83SK212019

Sponsored

  1. Home
  2. / Used Cars
  3. / Convertible
  4. / Indiana
  5. / Chesterton
Reviews

4.6 Overall rating

(36,586 reviews)
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.

Alba C
5.0
Reviewed a 2025 MINI S Signature Trim 2-door Hatchback on Dec 07, 2024

Love everything about it except all the beeping. Great ride, BMW comfort and power and cute as a button.

  • Used Convertibles for Sale Under $10,000

  • Used Convertibles for Sale Under $15,000

  • Used Convertibles for Sale Under $20,000

  • Used Convertibles for Sale Under $25,000

  • Used Convertibles for Sale Under $30,000

  • Used Convertibles for Sale Under $40,000

  • Convertibles in Chicago IL

  • Convertibles in South Bend IN

  • Convertibles in Palatine IL

  • Convertibles in Aurora IL

  • Convertibles in Kenosha WI

  • Convertibles in Lafayette IN

  • Convertibles in Kalamazoo MI

  • Convertibles in Kokomo IN

  • Convertibles in Holland MI

  • MINI Convertibles for Sale in Chesterton IN

  • BMW Convertibles for Sale in Chesterton IN

  • Ford Mustang GLX Convertible RWD

  • BMW 3 Series 328i Convertible RWD

  • Mercedes-Benz C-Class AMG C 43 Cabriolet

  • Chevrolet Corvette Sting Ray Convertible in Chesterton IN

  • Mercedes-Benz E-Class E 320 Convertible

  • MINI Cooper Convertible

  • BMW 4 Series 428i Convertible RWD

  • Chevrolet Camaro Convertible RWD

  • Mercedes-Benz S-Class S 550 Convertible

  • BMW 2 Series 228i xDrive Convertible AWD

  • Porsche 911 Carrera Targa Coupe RWD

  • Audi A5 2.0T Premium Cabriolet FWD

  • Used Electric Convertibles for Sale

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Highline Auto Sales

  • Adam Auto Group

  • Haus of Imports

  • Driven Auto Sales

  • Blue Sky Auto Sales - Crestwood

  • CCR Auto Sales

  • Baha Auto Sales

  • iDrive Motor Sports

  • Aston Martin Glenview

  • Loeber Motors

  • McGrath Lexus of Westmont

  • Silver Auto Sales and Service

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.