Used Convertibles for Sale Under $40,000 inChicago, IL

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126 vehicles found

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Year:
2024
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
315 hp 2.3L I4
Exterior color:
Oxford White
Combined gas mileage:
27 MPG
Fuel type:
Gasoline
Interior color:
Space Gray
Transmission:
Automatic
Mileage:
58,039
Stock #:
CU7778
VIN:
1FAGP8UH7R5117198
Oxford White 2024 Ford Mustang Convertible Rear-Wheel Drive Automatic
Price drop

-$900

Countryside Mitsubishi

Sponsored by Countryside Mitsubishi

2024 Ford Mustang

EcoBoost Premium Convertible RWD

58,039 mi

Countryside, IL
14 mi away
Good Deal

$24,773

$23,873

Year:
2023
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
134 hp 1.5L I3
Exterior color:
British Racing Green
Fuel type:
Gasoline
Interior color:
Carbon Black
Transmission:
7-Speed Automatic
Mileage:
14,252
Stock #:
MW19747
VIN:
WMW23DL02P3R13528
British Racing Green 2023 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
New arrival

Sponsored Listing

2023 MINI Cooper

Convertible FWD

14,252 mi

Naperville, IL
30 mi away
Good Deal
Manufacturer certified

$26,190

Year:
2022
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Snowflake White Pearl Mica
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Manual
Mileage:
26,211
Stock #:
27711G
VIN:
JM1NDAM74N0505876
Snowflake White Pearl Mica 2022 Mazda MX-5 Miata Convertible Rear-Wheel Drive 6-Speed Manual

Sponsored Listing

2022 Mazda MX-5 Miata

RF Grand Touring RWD

26,211 mi

Highland Park, IL
25 mi away
Fair Deal

$27,712

Year:
2026
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
315 hp 2.3L I4
Exterior color:
White
Combined gas mileage:
27 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5
Stock #:
261375
VIN:
1FAGP8UH4T5130224
White 2026 Ford Mustang Convertible Rear-Wheel Drive Automatic
Price drop

-$1,348

 

2026 Ford Mustang

EcoBoost Convertible RWD

Niles, IL
16 mi away

New car

MSRP $44,930

$40,849

$39,501

Year:
2020
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
310 hp 2.3L I4
Exterior color:
Oxford White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black (Ebony)
Transmission:
Automatic
Mileage:
101,000
Stock #:
36594
VIN:
1FATP8UH3L5136594
Oxford White 2020 Ford Mustang Convertible Rear-Wheel Drive Automatic

 

2020 Ford Mustang

EcoBoost Premium Convertible RWD

101,000 mi

Plano, IL
48 mi away
Fair Deal
Manufacturer certified

$16,998

Year:
2024
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
189 hp 2L I4
Exterior color:
Nanuq White Metallic
Fuel type:
Gasoline
Interior color:
Satellite Gray
Transmission:
7-Speed Automatic
Mileage:
20,826
Stock #:
T2585
VIN:
WMW43DL08R3S17543
Nanuq White Metallic 2024 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
Price drop

-$1,300

 

2024 MINI Cooper

S Convertible FWD

20,826 mi

Schaumburg, IL
25 mi away
Good Deal

$29,301

$28,001

Year:
2026
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
2L I4
Exterior color:
Green Metallic
Fuel type:
Gasoline
Interior color:
Nightshade Blue
Transmission:
7-Speed Automatic
Mileage:
6,295
Stock #:
MX47900
VIN:
WMW23GX01T2X90087
Green Metallic 2026 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic

 

2026 MINI Cooper

S Convertible FWD

6,295 mi

Naperville, IL
30 mi away
Good Deal
Manufacturer certified

$36,390

Year:
2026
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
2L I4
Exterior color:
Gray Metallic
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
7-Speed Automatic
Mileage:
5,753
Stock #:
MX48140
VIN:
WMW23GX03T2X94464
Gray Metallic 2026 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
Price drop

-$891

 

2026 MINI Cooper

S Convertible FWD

5,753 mi

Naperville, IL
30 mi away
Fair Deal
Manufacturer certified

$38,302

$37,411

Year:
2026
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Blue
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Transmission:
Manual
Mileage:
5
Stock #:
NM6347
VIN:
JM1NDAC73T0708885
Blue 2026 Mazda MX-5 Miata Convertible Rear-Wheel Drive Manual

 

2026 Mazda MX-5 Miata

Club RWD

Chicago, IL
9 mi away

New car

MSRP $35,530

$35,037

Year:
2025
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Jet Black Mica
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Manual
Mileage:
3,292
Stock #:
PM21607
VIN:
JM1NDAL74S0659484
Jet Black Mica 2025 Mazda MX-5 Miata Convertible Rear-Wheel Drive 6-Speed Manual

 

2025 Mazda MX-5 Miata

RF Club RWD

3,292 mi

Evanston, IL
11 mi away
Fair Deal
Manufacturer certified

$37,188

Year:
2021
Make:
Mercedes-Benz
Model:
C-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
All-Wheel Drive
Engine:
255 hp 2L I4
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Transmission:
9-Speed Automatic
Mileage:
44,337
Stock #:
P28001A
VIN:
W1KWK8EB5MG075213
 2021 Mercedes-Benz C-Class Convertible All-Wheel Drive 9-Speed Automatic

 

2021 Mercedes-Benz C-Class

C 300 Cabriolet 4MATIC

44,337 mi

Lisle, IL
23 mi away
Fair Deal

$34,012

Year:
2020
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
460 hp 5L V8
Exterior color:
Shadow Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black (Ebony W/Metal Gray Stitch)
Transmission:
Automatic
Mileage:
41,675
Stock #:
OF101152AA
VIN:
1FATP8FF4L5151925
Shadow Black 2020 Ford Mustang Convertible Rear-Wheel Drive Automatic

Sponsored Listing

2020 Ford Mustang

GT Premium Convertible RWD

41,675 mi

Oak Lawn, IL
13 mi away
Good Deal
Manufacturer certified

$32,743

Year:
2024
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
315 hp 2.3L I4
Exterior color:
Oxford White
Combined gas mileage:
27 MPG
Fuel type:
Gasoline
Interior color:
Space Gray
Transmission:
Automatic
Mileage:
58,039
Stock #:
CU7778
VIN:
1FAGP8UH7R5117198
Oxford White 2024 Ford Mustang Convertible Rear-Wheel Drive Automatic
Price drop

-$900

Countryside Mitsubishi

Sponsored by Countryside Mitsubishi

2024 Ford Mustang

EcoBoost Premium Convertible RWD

58,039 mi

Countryside, IL
14 mi away
Good Deal

$24,773

$23,873

Year:
2023
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
134 hp 1.5L I3
Exterior color:
British Racing Green
Fuel type:
Gasoline
Interior color:
Carbon Black
Transmission:
7-Speed Automatic
Mileage:
14,252
Stock #:
MW19747
VIN:
WMW23DL02P3R13528
British Racing Green 2023 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
New arrival

Sponsored Listing

2023 MINI Cooper

Convertible FWD

14,252 mi

Naperville, IL
30 mi away
Good Deal
Manufacturer certified

$26,190

Year:
2022
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Snowflake White Pearl Mica
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Manual
Mileage:
26,211
Stock #:
27711G
VIN:
JM1NDAM74N0505876
Snowflake White Pearl Mica 2022 Mazda MX-5 Miata Convertible Rear-Wheel Drive 6-Speed Manual

Sponsored Listing

2022 Mazda MX-5 Miata

RF Grand Touring RWD

26,211 mi

Highland Park, IL
25 mi away
Fair Deal

$27,712

Year:
2026
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
315 hp 2.3L I4
Exterior color:
White
Combined gas mileage:
27 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5
Stock #:
261375
VIN:
1FAGP8UH4T5130224
White 2026 Ford Mustang Convertible Rear-Wheel Drive Automatic
Price drop

-$1,348

 

2026 Ford Mustang

EcoBoost Convertible RWD

Niles, IL
16 mi away

New car

MSRP $44,930

$40,849

$39,501

Year:
2020
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
310 hp 2.3L I4
Exterior color:
Oxford White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black (Ebony)
Transmission:
Automatic
Mileage:
101,000
Stock #:
36594
VIN:
1FATP8UH3L5136594
Oxford White 2020 Ford Mustang Convertible Rear-Wheel Drive Automatic

 

2020 Ford Mustang

EcoBoost Premium Convertible RWD

101,000 mi

Plano, IL
48 mi away
Fair Deal
Manufacturer certified

$16,998

Year:
2024
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
189 hp 2L I4
Exterior color:
Nanuq White Metallic
Fuel type:
Gasoline
Interior color:
Satellite Gray
Transmission:
7-Speed Automatic
Mileage:
20,826
Stock #:
T2585
VIN:
WMW43DL08R3S17543
Nanuq White Metallic 2024 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
Price drop

-$1,300

 

2024 MINI Cooper

S Convertible FWD

20,826 mi

Schaumburg, IL
25 mi away
Good Deal

$29,301

$28,001

Year:
2026
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
2L I4
Exterior color:
Green Metallic
Fuel type:
Gasoline
Interior color:
Nightshade Blue
Transmission:
7-Speed Automatic
Mileage:
6,295
Stock #:
MX47900
VIN:
WMW23GX01T2X90087
Green Metallic 2026 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic

 

2026 MINI Cooper

S Convertible FWD

6,295 mi

Naperville, IL
30 mi away
Good Deal
Manufacturer certified

$36,390

Year:
2026
Make:
MINI
Model:
Cooper
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Front-Wheel Drive
Engine:
2L I4
Exterior color:
Gray Metallic
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
7-Speed Automatic
Mileage:
5,753
Stock #:
MX48140
VIN:
WMW23GX03T2X94464
Gray Metallic 2026 MINI Cooper Convertible Front-Wheel Drive 7-Speed Automatic
Price drop

-$891

 

2026 MINI Cooper

S Convertible FWD

5,753 mi

Naperville, IL
30 mi away
Fair Deal
Manufacturer certified

$38,302

$37,411

Year:
2026
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Blue
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Transmission:
Manual
Mileage:
5
Stock #:
NM6347
VIN:
JM1NDAC73T0708885
Blue 2026 Mazda MX-5 Miata Convertible Rear-Wheel Drive Manual

 

2026 Mazda MX-5 Miata

Club RWD

Chicago, IL
9 mi away

New car

MSRP $35,530

$35,037

Year:
2025
Make:
Mazda
Model:
MX-5 Miata
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
181 hp 2L I4
Exterior color:
Jet Black Mica
Combined gas mileage:
30 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Manual
Mileage:
3,292
Stock #:
PM21607
VIN:
JM1NDAL74S0659484
Jet Black Mica 2025 Mazda MX-5 Miata Convertible Rear-Wheel Drive 6-Speed Manual

 

2025 Mazda MX-5 Miata

RF Club RWD

3,292 mi

Evanston, IL
11 mi away
Fair Deal
Manufacturer certified

$37,188

Year:
2021
Make:
Mercedes-Benz
Model:
C-Class
Body type:
Convertible
Doors:
2 doors
Drivetrain:
All-Wheel Drive
Engine:
255 hp 2L I4
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Transmission:
9-Speed Automatic
Mileage:
44,337
Stock #:
P28001A
VIN:
W1KWK8EB5MG075213
 2021 Mercedes-Benz C-Class Convertible All-Wheel Drive 9-Speed Automatic

 

2021 Mercedes-Benz C-Class

C 300 Cabriolet 4MATIC

44,337 mi

Lisle, IL
23 mi away
Fair Deal

$34,012

Year:
2020
Make:
Ford
Model:
Mustang
Body type:
Convertible
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
460 hp 5L V8
Exterior color:
Shadow Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black (Ebony W/Metal Gray Stitch)
Transmission:
Automatic
Mileage:
41,675
Stock #:
OF101152AA
VIN:
1FATP8FF4L5151925
Shadow Black 2020 Ford Mustang Convertible Rear-Wheel Drive Automatic

Sponsored Listing

2020 Ford Mustang

GT Premium Convertible RWD

41,675 mi

Oak Lawn, IL
13 mi away
Good Deal
Manufacturer certified

$32,743

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