Used Oldsmobile Classic Cars in Chicago, IL For Sale (23 results)
Sort by:
Refine search
Sort by:
Year
-
(1)1986
-
(1)1976
-
(4)1972
-
(2)1971
-
(3)1970
-
(1)1969
-
(3)1968
-
(2)1967
-
(2)1966
-
(1)1963
-
(1)1961
-
(1)1959
-
(1)1955
Zip
Price
-
(5)under $10,000
-
(6)under $11,000
-
(7)under $12,000
-
(7)under $13,000
-
(8)under $14,000
-
(8)under $15,000
-
(11)under $20,000
-
(14)under $25,000
-
(15)under $30,000
-
(15)under $40,000
-
(17)under $50,000
Mileage
-
(9)0 - 50000
-
(12)50000 - 100000
-
(2)100000 - 150000
Make
-
(327)Chevrolet
-
(239)Ford
-
(55)Pontiac
-
(44)Porsche
-
(39)Cadillac
-
(38)Volkswagen
-
(34)Mercedes-Benz
-
(33)Plymouth
-
(27)Dodge
-
Oldsmobile
-
(22)Toyota
-
(18)Buick
-
(17)Jaguar
-
(16)Jeep
-
(15)Rolls-Royce
-
(13)Lincoln
-
(10)Chrysler
-
(10)Datsun
-
(10)VAZ (Lada)
-
(9)Alfa Romeo
-
(9)Ferrari
-
(9)International
-
(9)MG
-
(8)Austin-healey
-
(8)BMW
-
(8)Willys-overland
-
(7)Shelby
-
(6)AMC
-
(6)GMC
-
(5)Land Rover
Model
-
(9)Cutlass
-
(7)442
-
(1)98
-
(1)Dynamic 88
-
(1)Hurst
-
(1)Ninety-Eight
-
(1)Starfire
-
(1)Super 88
-
(1)Toronado
Transmission type
-
(14)automatic
-
(3)manual
Color
-
(5)Red
-
(3)White
-
(1)Silver
Body
-
(8)
![]()
Convertible -
(7)
![]()
Coupe
Drive
-
(1)fwd
-
(1)rwd
Fuel
-
(12)gasoline
Category
-
classic cars
-
(1)hot rod
State
City
Features
-
(9)Air conditioning
-
(9)Power steering
-
(8)Power windows
-
(6)Power brakes
-
(4)AM/FM radio
-
(4)Bucket seats
-
(2)Power disc brakes
-
(2)Power locks
-
(2)Tachometer
-
(2)Tilt wheel
-
(1)Chrome bumpers
-
(1)Clear title
-
(1)Leather seats
-
(1)New tires
-
(1)Power seats
-
(1)Rear spoiler
1970 oldsmobile 442 in chicago, illinois
This stunning 1970 Oldsmobile 442 showcases a superb restoration with its Matador Red paint and immaculate Pearl White interior. Equipped with a powerful 455 CI V-8 and factory A/C, it's a classic that combines performance with elegance
![]()
Coupe
Chicago, IL
57,320 mi.
Red
Coupe
automatic
gasoline
Chicago, IL
$139,500
1966 oldsmobile cutlass 95470 miles almond coupe 330 cid v8 automatic
Discover a time capsule with this 1966 Oldsmobile Cutlass 2-door. With its original Almond Beige exterior and a comfortable red bench seat, this classic car features a high compression V8 engine, power steering, and newly upgraded disc brakes for a smooth ride
![]()
$1 door
Chicago, IL
95,470 mi.
Almond
$1 door
automatic
Chicago, IL
1968 oldsmobile 98 71054 miles bright red convertible 455 cid v8 automatic
This 1968 Oldsmobile Ninety-Eight convertible combines vintage charm with a powerful big block 455 Rocket V8 engine. Perfect for cruising, it comfortably seats six and features a power convertible top, making it a luxurious drive
![]()
Convertible
Chicago, IL
71,054 mi.
Red
Convertible
automatic
Chicago, IL
1967 oldsmobile cutlass supreme 442 convertible 4-speed
This classic 1967 Oldsmobile Cutlass Supreme 442 Convertible features a powerful 400ci V8 and a four-speed manual transmission. Enjoy the smooth ride with air conditioning and power windows
![]()
Convertible
Chicago, IL
60,000 mi.
Red
Convertible
manual
gasoline
Chicago, IL
$21,600
1971 oldsmobile cutlass convertible painted a creamy white color
This stunning 1971 Oldsmobile Cutlass convertible in creamy white boasts a powerful Rocket 350 V8 engine and classic features like a power convertible top, air conditioning, and an upgraded stereo system
![]()
Convertible
Chicago, IL
80,000 mi.
White
Convertible
automatic
Chicago, IL
$8,100
1955 oldsmobile super 88
Experience classic American muscle with this beautifully maintained 1955 Oldsmobile Super 88, featuring a powerful Rocket V8 engine, automatic transmission, and comfortable 2 Tone vinyl interior
Chicago, IL
automatic
gasoline
Chicago, IL
$15,000
1959 oldsmobile 98 convertible coupe
This 1959 Oldsmobile 98 Convertible Coupe is a classic beauty in Cardinal Red with a stunning tri-color interior. It's loaded with power options and boasts a powerful 394 cubic inch engine with 315 horsepower. A true collector's dream!
![]()
Convertible coupe
Chicago, IL
102,694 mi.
Red
Convertible coupe
automatic
Chicago, IL
$7,100
1971 oldsmobile 442 4 speed convertible with minimal body rust
This rare 1971 Oldsmobile 442 4-speed convertible, one of only 183 produced, features minimal body rust with a solid bottom condition for its age. It hasn't run since the '90s but is a hard-to-find gem worth restoring
![]()
Convertible
Chicago, IL
91,000 mi.
Convertible
Chicago, IL
$7,100
oldsmobile cutlass 442 coupe
This stunning 1969 Oldsmobile Cutlass 442 Coupe features a rebuilt numbers matching 400 CI engine, delivering classic performance and charm in a timeless design
![]()
Coupe
Chicago, IL
4,168 mi.
Coupe
gasoline
Chicago, IL
$23,100
1986 oldsmobile cutlass ciera sl 2dr coupe fwd v6 2.8l gasoline
This elegant 1986 Oldsmobile Cutlass SL 2dr Coupe, finished in crisp white, sports a powerful 2.8L V6 engine. It comes equipped with modern conveniences such as power windows and air conditioning, making it a timeless classic for any collector
Chicago, IL
137,526 mi.
White
automatic
gasoline
Chicago, IL
$450,000
1967 oldsmobile 442 rally red finish excellent chrome
This stunning 1967 Oldsmobile 442 boasts a beautiful Rally Red finish and features a full restoration that includes a powerful 455ci engine and a luxurious black interior with Strato-bucket seats. A true classic ready to impress!
Chicago, IL
32,597 mi.
Chicago, IL
$18,500
1966 oldsmobile toronado in chicago, illinois
This highly original 1966 Oldsmobile Toronado from California has just 77,000 miles on the clock, making it a rare find for classic car enthusiasts
Chicago, IL
77,000 mi.
Chicago, IL
$46,500
1970 oldsmobile 442 convertible 455 auto 12 bolt ac ps pdb tac
This stunning 1970 Oldsmobile 442 Convertible boasts a matching numbers 455 engine, a pristine Matador Red exterior, and a new white power convertible top. Enjoy the classic power steering and upgraded tach gauges in a stylish white bucket seat interior
![]()
Convertible
Chicago, IL
91,300 mi.
Red
Convertible
automatic
Chicago, IL
$13,300
1972 oldsmobile cutlass
This classic 1972 Oldsmobile Cutlass features a sleek coupe design with a manual transmission, making it a perfect choice for enthusiasts looking for a vintage ride
![]()
Coupe
Chicago, IL
91,093 mi.
Coupe
manual
gasoline
Chicago, IL
$24,200
1976 oldsmobile cutlass s colonnade ht coupe one owner only 63k miles
This 1976 Oldsmobile Cutlass S is a rare one-owner coupe with only 63,442 miles. It's well-documented with a clear title and original paperwork. Featuring a full vinyl roof and rustproofing, this classic car is a charming find for any enthusiast
![]()
Coupe
Chicago, IL
63,442 mi.
Silver
Coupe
automatic
gasoline
Chicago, IL
1963 oldsmobile dynamic 88
Discover the classic elegance of this 1963 Oldsmobile Dynamic 88 Convertible, a stunning Starfire Clone that combines timeless style with modern comfort. Perfect for cruising around town or taking to car shows
![]()
Convertible
Chicago, IL
46,101 mi.
Convertible
automatic
gasoline
Chicago, IL
$15,900
1968 oldsmobile hurst
This 1968 Oldsmobile Hurst is a well-maintained example of a rare model, showcasing its uniqueness and above-average condition
![]()
Unspecified
Chicago, IL
92,957 mi.
Unspecified
automatic
gasoline
Chicago, IL
$45,000
1970 oldsmobile 442 oldsmobile sports roof original 455 upgraded
This 1970 Oldsmobile 442 Sports Roof is a true classic featuring an original 455 engine and a Turbo 400 automatic transmission. It includes upgrades like a new AC system, fresh tires, and a Flow Master exhaust, making it a thrilling drive
![]()
Sports roof
Chicago, IL
59,241 mi.
Sports roof
automatic
Chicago, IL
$11,400
1972 oldsmobile cutlass convertible cool classic attitude 25239 miles
Experience the charm of the 1972 Oldsmobile Cutlass Convertible, boasting classic vintage style with an eye-catching saddle bronze paint and a cool A/C interior – a true road-ready cruiser with a nostalgic feel
![]()
Convertible
Chicago, IL
25,239 mi.
Convertible
Chicago, IL
$10,800
1968 oldsmobile 442
This 1968 Oldsmobile 442 is a meticulously restored muscle car, featuring a complete frame-off restoration. Every detail has been attended to, making it truly one-of-a-kind
![]()
Coupe
Chicago, IL
31,400 mi.
Coupe
manual
gasoline
Chicago, IL
$26,600
- 1
- 2