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Classic Cars For Sale In Chicago

99 Classics To Choose From

Chicago

Powered by a 350 V-8 GM V8 engine with a Turbo 400 3-Speed Automatic transmission. Champagne exterior. Camel interior.

Powering this beast is a 350 cubic inch Chevrolet V8 paired with a TH-400 3-speed automatic transmission. Power is sent to a chrome Ford 9' rear axle spinning the massive 'steamroller'... See More

Chicago

Powered by a I4 engine with a 3-Speed Manual transmission. Light Green Gray Black exterior. Brown interior.

The model A was the replacement of the very popular model T and was the first Ford to use a standard set of driver controls including a conventional clutch and brake... See More

Chicago

Powered by a 350 CID Crate V8 engine with a 5-Speed Tremec Manual transmission. Flat Black exterior. Black interior.

Powering this flat black custom is a 350 cubic inch Chevrolet small block V8. Power is sent through a T5 5-speed manual transmission to a 10-bolt rear axle. The engine is... See More

Chicago

1936 Ford Custom

Humpback

Powered by a 350 CID V8 engine with a 4-Speed Manual transmission. Dark Blue exterior. Brown interior.

Under the hood is a healthy 350 cubic inch Chevrolet V8 sending power through a 4-speed manual transmission to the rear wheels. The bright blue metallic paint sparkles in the sun... See More

Chicago

1939 Ford Cabriolet

Coast to Coast

Powered by a 5.7L LS1 engine with a T56 transmission. Tangerine Pearl with Flames exterior. Saddle interior.

Built on a Coast to Coast body, this fiberglass replica has dimensions that a steel body can only dream about. the long, swooping fenders, the extra wide side steps, the chopped... See More

Chicago

Powered by a 322 Cubic Inch V8 engine with a 3-Speed Manual transmission. Burgundy exterior. Red/ Tan interior.

The luxury and class of a bygone era are apparent in this fine Automobile. The LaSalle was marketed as a companion marque to the Cadillac, priced slightly lower but just as... See More

Chicago

Powered by a Inline 8 CYL. engine with a 3-Speed Manual//W Overdrive Manual transmission. Matador Maroon exterior. Beige interior.

A true American Luxury Car, This Elegant cruiser boasts the 327 in line 8 cyl and 3 speed with overdrive transmission. For its first new postwar models of 1948's the 22... See More

Chicago

Powered by a 350 CID V8 engine with a 3-Speed Automatic transmission. Magenta/ Silver exterior. Gray interior.

This hot-rodded Chevy has come a long way since 1948! Under the hood sits a healthy 350 cubic inch small block Chevrolet V8 paired to a 3-speed automatic transmission. That's a... See More

Chicago

1949 Oldsmobile 88

2S Restomod

Powered by a 350 Chevy V8 engine with an Overdrive 700 R4 Automatic transmission. Burgundy exterior. Burgundy interior.

This vehicle has been lovingly restored to be better than new. It features a Mustang 2 front end with a 1992 GM 350 bored to 30 over, and a 700 R... See More

Chicago

Powered by a 472 Cadillac V8 engine with a 200R Overdrive Automatic transmission. Sienna Red exterior. White Pearl interior.

This chop-top and dropped Merc is a true beauty. this lean mean machine was recently finished, and was modified in all the old-school ways. Rather than bondo and filler, the chop... See More

Chicago

Powered by a Flat Head V8 engine with a 2-Speed Automatic transmission. Burgundy exterior. Gray interior.

Under the hood is a strong-running flathead V8 engine paired to a Ford-O-Matic automatic transmission. The vehicle has had a restoration done 20+ years ago and has been maintained very well.... See More

Chicago

Powered by a 302 V8 engine with a 3-Speed Automatic transmission. Blue exterior. Gray interior.

This Ford has come a long way since it first rolled off the assembly line. Many modern upgrades have been fitted on the classic steel body, making for all the stylish... See More

Chicago

1953 Chevrolet 3100

Pick Up 5 Window

Powered by a I6 engine with a 3 On The Tree Manual transmission. Green exterior. Tan interior.

This is part of Chevy's advance-design after war production of cab over fenders Pick Up trucks. This one still features the 216 CI Inline 6 cylinder paired to the 3 speed,... See More

Chicago

Powered by a 235 I6 engine with a Power Glide Automatic transmission. Red/White exterior. Red/White interior.

This Red and White beauty is powered by a Corvette Engine! That's right! The smooth-running 235 cubic inch Blue Flame inline-6 cylinder engine is paired to a 2-speed Powerglide automatic transmission... See More

Chicago

Powered by a 292 CID V8 engine with an Automatic transmission. Red exterior. Red White interior.

An icon for everything from a sports car to a luxury coupe, and even as a forced-fed, muscle-bound stoplight warrior and NASCAR champion in the 80's and '90s. Most consider the... See More

Chicago

Powered by a 482 CID V8 engine with a TH400 Automatic transmission. Beige exterior. Beige interior.

Powering this full-size heavy-hitter is a 409-base 482 cubic inch V8 sending power through a 3-speed automatic TH-400 transmission that was rebuilt by T. S. I. Our back sits a Ford... See More

Chicago

1965 Austin Mini

Cooper S

Powered by a 1275 with Twin CARBS, LCB Headers and Singl engine with a 4-Speed Manual transmission. Silver/Black exterior. Grey/Black interior.

This right hand drive Mini is an absolute riot to speed around town thanks to a rev-happy 1275cc inline 4-cylinder. Though only rated around 60 horsepower, the low weight of around... See More

Chicago

1965 Ford Mustang

Convertible

Powered by a V8 engine with an Automatic transmission. Rangoon Red exterior. Black interior.

This one Boasts a peppy V-8 mated to an automatic transmission that really makes this a fun car to drive. Its done up in the Classic Ford Ragoon Red with a... See More

Chicago

Powered by a 390 V8 engine with an Automatic transmission. Black exterior. White interior.

This beauty is equipped with the standard 390 cubic inch V8 and an automatic transmission. The black exterior offsets nicely with the white interior, making this one sharp car. Start up... See More

Chicago

Powered by a V8 engine with a 4-Speed Manual transmission. Turquoise exterior. Black interior.

This hardtop Pontiac is sporting a 389 cubic inch V8 that is believed to be original to the car. The 3-speed manual that was factory has been removed in favor of... See More

Chicago

1966 Ford Mustang

Rad Rides by Troy

Powered by a 302 CID V8 engine with a 4R70W 4-Speed Overdrive Automatic transmission. Gunmetal Blue Metallic exterior. Black interior.

This was an in-house build by the very well renowned Rad Rides by Troy as a 10-year build. The Mustang saw a complete transformation as it was completely stripped to bare... See More

Chicago

Powered by a 327 V-8 V8 engine with an Automatic transmission. Yellow exterior. Black interior.

This Caprice's exterior is Chevy's Lemonwood yellow, with a luxurious black vinyl roof and a black vinyl and cloth inlaid bench seat that really shows well. The 1966 is part of... See More

Chicago

1966 Ford Mustang

200 CID I-6

Powered by a 200 CID I6 engine with a 3-Speed Manual transmission. Rangoon Red exterior. Black interior.

This '66 coupe has a 200 cubic inch inline-six engine with a 3-speed manual transmission. The Mustang is wearing a clean coat of red paint over a black vinyl interior. Though... See More

Chicago

Powered by a 496 V8 engine with a TH400 3-Speed with Lock Out Automatic transmission. Black exterior. Black interior.

Under the scooped hood is a monstrous 496 cubic inch big block. With fuel injection, a thumping camshaft, and a build sheet nearing $10k, this engine is built to do it... See More

Chicago

Powered by a 289 CID V8 engine with a 3-Speed Automatic transmission. Burgundy exterior. Black interior.

Under the hood is a peppy 289 cubic inch Ford V8 paired to a 3-speed automatic transmission. The Mustang saw a lot of restoration work between 1999 and 2007 and has... See More

Chicago

1966 Ford Mustang

Convertible

Powered by a V8 engine with a 5-Speed Manual transmission. Turquoise exterior. Light Blue interior.

Though badged as a 289, a strong running 302 cubic inch V8 is tucked under the hood. Adding to the 'sleeper' status, the shift knob shows a 4-speed pattern, but its... See More

Chicago

Powered by a Straight 4 Cylinder I4 engine with a 4-Speed Manual transmission. White exterior. Black interior.

We never see these vehicles anymore. Like just about every postwar all-wheel drive vehicle, the genesis of the original Land Rover is based upon the success of the World War II... See More

Chicago

Powered by a 289 CID V8 engine with a 4-Speed Manual transmission. Emerald Green Metallic exterior. Black interior.

The Ranchero's are becoming very rare. Many people think the El Camino came first but actually Chevy brought that to market to compete with the popularity of the already established Ranchero.... See More

Chicago

1967 Pontiac Firebird

Convertible

Powered by a 400 Cu V8 engine with a 5-Speed Manual transmission. Red exterior. Red interior.

Under the hood is a Pontiac 400 V8 engine, with a Holley sniper electronic fuel injection, paired to a Tremec TKO 5-speed manual transmission. It has the classic old school sound... See More

Chicago

Powered by a FLAT-4 Cylinder engine with a 4-Speed Manual transmission. Blue/Flames exterior. Gray interior.

As you can see, many changes have been made from when this car was new! Powering this little Bug is a 4-cylinder and 4-speed manual transmission. the stinger-style exhaust makes for... See More

Classic Cars For Sale In Chicago

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Rel. November 18, 2022