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Used 1969 Oldsmobile 442 for sale near Chicago, IL

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6 matches All miles from 60608
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Est. $400 /mo*
Down Payment
$0
Net trade-in value
$0
Months
72
APR
7.0%
Sales tax
0.0%

*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.

**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.

1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442 View all 53 photos

Used

1969 Oldsmobile 442

24,000 mi.
$43,990
Est. $827/mo*
Get the AutoCheck Report
Exotic Car Trader
(10 reviews)
Fort Lauderdale, FL (1,167 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Gold
Int. color: Black
Drivetrain: Rear-wheel Drive
Fuel type: Gasoline
Transmission: 3-Speed Automatic
Engine: 400ci V8
Stock #: NE-250129307
VIN: 3448791113710

Reviews

Exotic Car Trader review

Very professional and patient with my schedule, and

July 17, 2025
By Scott from Monterey, California

Very professional and patient with my schedule, and always disciplined in following up with my inquiries in a timely fashion.

1969 Oldsmobile 442 review

Muscle Car Mania

July 31, 2017
By Cutlass442tenir from Missouri
Used to own this car

All time favorite car. I owned one at the age of 18 in 1975. Sold it in 2008. Should have never sold it for $18,000 I regret ever selling it
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442 View all 99 photos

Used

1969 Oldsmobile 442

94,020 mi.
$38,900
Est. $731/mo*
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GR Auto Gallery
(283 reviews)
Grand Rapids, MI (130 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Burgundy
Int. color: Black
Drivetrain: Rear-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 455ci V8
Stock #: B6070 J
VIN: 336879M106384

Features

Exterior: Sunroof/Moonroof
Seating: Leather Seats

Reviews

GR Auto Gallery review

Fair negotiation.

July 27, 2025
By Laurent from Berkeley, CA

Fair negotiation. Fast process. No complaints, I’d buy a vehicle from here again. Jacob helped me and I appreciated his transparency and help throughout the entire process.
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442 View all 80 photos

Used

1969 Oldsmobile 442

88,732 mi.
$189,969
Est. $3,571/mo*
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Joe Basil Chevrolet
(1,556 reviews)
Depew, NY (464 mi.)
Call Check availability Check availability

Vehicle information

Stock #: C189
VIN: 344879M406294

Reviews

Joe Basil Chevrolet review

Joe Basil was very quick to respond to my inquiry!

July 31, 2025
By M.Berry from Simpsonville, SC

Joe Basil was very quick to respond to my inquiry! They even reached back out to me to see if there were any other questions I might have.
1969 Oldsmobile 442 Hardtop
1969 Oldsmobile 442 Hardtop
1969 Oldsmobile 442 Hardtop
1969 Oldsmobile 442 Hardtop
1969 Oldsmobile 442 Hardtop
1969 Oldsmobile 442 Hardtop View all 27 photos

Used

1969 Oldsmobile 442 Hardtop

96,917 mi.
$29,900
Est. $562/mo*
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Kinion Auto Sales
(25 reviews)
Clarence, IA (175 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Silver
Int. color: Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 455
Stock #: 1969a
VIN: 344879E182884

Reviews

Kinion Auto Sales review

Michael and Adam are the two best salesman in the

July 24, 2025
By John Christie from CADIZ Kentucky,

Michael and Adam are the two best salesman in the country. They tell you the truth they deliver a beautiful product if I was looking for another classic, those would be the two guys I’d go see you can believe them and they will deliver. There’s no games played no hassles these guys take really good care. They are awesome and I want to thank them one more time for everything they did in that GTO is beautiful.
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442
1969 Oldsmobile 442 View all 99 photos

Used

1969 Oldsmobile 442

39,539 mi.
$60,000
Est. $1,128/mo*
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Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Blue
Int. color: White
Transmission: Automatic
Engine: V8
Stock #: PHY1855
VIN: GCCPHY1855

Reviews

Gateway Classic Cars review

Very helpful when looking for a car will definitely be

July 27, 2025
By Rgjudd from Snowflake az

Very helpful when looking for a car will definitely be doing business with them in the future

There are 14 matching cars close to your year range.

1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442 View all 87 photos

Used

1968 Oldsmobile 442

80,807 mi.
$42,768
Est. $804/mo*
Get the AutoCheck Report
Joe Basil Chevrolet
(1,556 reviews)
Depew, NY (464 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Blue
Stock #: CC917
VIN: 00003448781105753
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442 View all 71 photos

Used

1970 Oldsmobile 442

91,443 mi.
$89,950
Est. $1,691/mo*
Get the AutoCheck Report
Fusion Luxury Motors
Los Angeles, CA (1,752 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: White
Transmission: 3-Speed
Engine: 8
Stock #: 5682113
VIN: 344870M228696
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442 View all 59 photos

Used

1970 Oldsmobile 442

62,279 mi.
$84,900 $5,000 price drop
Est. $1,596/mo*
Get the AutoCheck Report
L.R.A. Enterprises
Bristol, PA (677 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: White
Stock #: P2277C
VIN: 344670M311038
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442 View all 99 photos

Used

1970 Oldsmobile 442

38,347 mi.
$75,000
Est. $1,410/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Bamboo
Int. color: Tan
Transmission: Automatic
Engine: 455 CID V8
Stock #: CHA645
VIN: GCCCHA645
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442 View all 99 photos

Used

1967 Oldsmobile 442

68,795 mi.
$58,000
Est. $1,090/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Black
Int. color: White
Transmission: Automatic
Engine: V8
Stock #: ATL2821
VIN: GCCATL2821

Features

Seating: Leather Seats
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442 View all 99 photos

Used

1967 Oldsmobile 442

3,094 mi.
$36,000 $4,000 price drop
Est. $677/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Blue
Int. color: Black
Transmission: 4 Speed Manual
Engine: 400 CI V8
Stock #: LOU3114
VIN: GCCLOU3114
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442
1970 Oldsmobile 442 View all 99 photos

Used

1970 Oldsmobile 442

94,619 mi.
$93,000
Est. $1,748/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: White /Black Stripes
Int. color: Black
Transmission: 4 speed Manual
Engine: 455 V8
Stock #: CHI2484
VIN: GCCCHI2484
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442
1968 Oldsmobile 442 View all 99 photos

Used

1968 Oldsmobile 442

62,232 mi.
$33,000 $1,000 price drop
Est. $620/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Willow Gold
Int. color: Willow Gold
Transmission: Automatic
Engine: 455ci V8
Stock #: LVS1165
VIN: GCCLVS1165
1970 Oldsmobile 442 Convertible
1970 Oldsmobile 442 Convertible
1970 Oldsmobile 442 Convertible
1970 Oldsmobile 442 Convertible
1970 Oldsmobile 442 Convertible
1970 Oldsmobile 442 Convertible View all 99 photos

Used

1970 Oldsmobile 442 Convertible

26,189 mi.
$99,000
Est. $1,861/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Twilight Blue
Int. color: White
Transmission: 4 Speed Muncie Manual
Engine: L31 455 CID V8
Stock #: DFW2889
VIN: GCCDFW2889
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442 View all 99 photos

Used

1967 Oldsmobile 442

3,410 mi.
$31,000
Est. $583/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Gray
Int. color: Black
Transmission: 700R4 Automatic
Engine: 383CID V8
Stock #: TUL547
VIN: GCCTUL547
1968 Oldsmobile 442 Convertible
1968 Oldsmobile 442 Convertible
1968 Oldsmobile 442 Convertible
1968 Oldsmobile 442 Convertible
1968 Oldsmobile 442 Convertible
1968 Oldsmobile 442 Convertible View all 99 photos

Used

1968 Oldsmobile 442 Convertible

4,319 mi.
$80,000
Est. $1,504/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Maroon
Int. color: Black
Transmission: 4L60E Automatic
Engine: 5.3l V8
Stock #: TPA2985
VIN: GCCTPA2985
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442
1967 Oldsmobile 442 View all 99 photos

Used

1967 Oldsmobile 442

62,131 mi.
$36,000
Est. $677/mo*
Get the AutoCheck Report
Gateway Classic Cars
(319 reviews)
O Fallon, IL (256 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Champaign
Int. color: Black
Transmission: Manual
Engine: V8
Stock #: CHI2373
VIN: GCCCHI2373
No photo available

Used

1971 Oldsmobile 442 W30

6,838 mi.
$69,997
Est. $1,316/mo*
Get the AutoCheck Report
Skyway Classics
Bradenton, FL (1,031 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Silver
Int. color: Black
Fuel type: Gasoline
Transmission: automatic
Engine: 455 V8
Stock #: SN2615
VIN: 344871M218633
1971 Oldsmobile 442
1971 Oldsmobile 442
1971 Oldsmobile 442
1971 Oldsmobile 442
1971 Oldsmobile 442
1971 Oldsmobile 442 View all 99 photos

Used

1971 Oldsmobile 442

114 mi.
$64,900 $2,000 price drop
Est. $1,220/mo*
Get the AutoCheck Report
GR Auto Gallery
(283 reviews)
Grand Rapids, MI (130 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Green
Int. color: White
Drivetrain: Rear-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 455ci V8
Stock #: B6034 B
VIN: 342671M218579

Features

Entertainment: USB Port
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*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.

**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.

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Research the 1969 Oldsmobile 442
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