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Classic Cars and Trucks For Sale In Chicago

Your Classic, Exotic, and Muscle Car Headquarters

176 Vehicles Found

Recent Arrival

1946 Ford Convertible

This Boyd Red, with Tan interior, 1946 Convertible is powered by a 420 CID EFI V8 engine with a 700-R4 Automatic transmission.

$95,000

2534-CHI

36 Views

1946 Ford Convertible

View Description

This classic beauty was collab project built by Hot Rod Designers and builders Boyd Coddington and Chip Foose! It is a testament to timeless design and modern engineering that they were both so well known for. This beauty features a robust Lingenfelter 420 CID EFI V8 engine under the hood. Paired with a 700-R4 automatic transmission, this Boyd Built Ford promises a driving experience that seamlessly blends vintage charm with contemporary performance. Step inside to discover tan leather interior that complements the vivid Boyd Red exterior. The cabin is equipped with features designed to enhance comfort and convenience. Enjoy the pleasure of air conditioning, power windows, power steering, and power brakes provide effortless control and ease of use, making every drive a pleasure. This classic Ford also caters to your entertainment needs with an AM/FM radio and CD player, allowing you to enjoy your favorite tunes as you cruise down the open road. The tilt steering wheel offers adjustable comfort, ensuring that drivers...

New Arrival

1969 Ford Fairlane

Cobra

This Red, with Black interior, 1969 Fairlane is powered by a 428 Cobra Jet V8 engine with a C6 Automatic transmission.

$48,000

2538-CHI

50 Views

1969 Ford Fairlane

View Description

This iconic vehicle boasts a striking red exterior that captures the essence of the muscle car era. Under the hood, you'll find the legendary 428 Cobra Jet V8 engine, a powerhouse that delivers the exhilarating performance enthusiasts crave. Paired with a C6 automatic transmission, this Fairlane Cobra offers a seamless driving experience. Inside, the Fairlane Cobra features a sleek black vinyl interior that complements its bold exterior. The cabin is equipped with an AM radio, providing a touch of nostalgia as you cruise along. For added convenience and driving comfort, this classic car comes with power steering, power brakes and radial tires ensuring a...

New Arrival

1931 Ford Model A

Convertible

This Blue, with Brown interior, 1931 Model A is powered by a 201 4 Cylinder engine with an A7006B Manual transmission.

$38,000

2526-CHI

31 Views

1931 Ford Model A

View Description

This vintage vehicle boasts a striking blue exterior that complements its era, making it a standout choice for enthusiasts and collectors alike. The Model A's timeless appeal is further accentuated by its manual convertible top, allowing you to enjoy open-air driving and fully immerse yourself in the nostalgic experience of motoring from a bygone era. Step inside, and you'll be greeted by a beautifully appointed brown leather interior. The leather seating provides both comfort and a touch of elegance, enhancing the overall aesthetic of this remarkable vehicle. The attention to detail in the interior design is a testament to the quality and care that went into manufacturing this classic car. Under the hood, the 1931 Ford Model A is powered by a reliable 201 cubic inch 4-cylinder engine, delivering a driving experience that is both smooth and engaging. Paired with the A7006B manual transmission, this vehicle offers an authentic and hands-on driving experience, allowing you to fully appreciate the mechanical simplicity and engineering of the era. Adding to the visual appeal are the distinctive white walls and wire wheels, which not only enhance the vehicle's classic look but also reflect the style and sophistication...

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Recent Arrival

1941 Buick Super

Model 50 4 door sedan

This Green, with Brown interior, 1941 Super is powered by a Straight 8 248 CID V8 engine with a Manual transmission.

$24,000

2533-CHI

34 Views

1941 Buick Super

View Description

This vintage vehicle is a testament to the elegance and craftsmanship of its era, showcasing a striking green exterior that captures the essence of timeless style. Under the hood, you'll find the robust 8 248 cubic inch V8 engine, paired with a manual transmission. This combination offers a driving experience that connects you directly with the road, providing a sense of control and engagement that modern vehicles often lack. The cabin is equipped with an AM radio, offering a touch of nostalgia and a reminder of the days when radio was king. The inclusion of seatbelts adds a layer of safety, reflecting a thoughtful integration of modern considerations into this classic vehicle. These features highlight the attention to...

New Arrival

1979 Ford Ranchero

500

This Light Metallic Jade, with Jade Green interior, 1979 Ranchero is powered by a 302 V8 engine with a C4 Automatic transmission.

$20,000

2531-CHI

42 Views

1979 Ford Ranchero

View Description

This Ranchero boasts a striking light metallic jade exterior that is sure to turn heads wherever you go. Complementing its exterior is a harmonious jade green interior, creating a seamless and sophisticated look that is both inviting and timeless. Under the hood, the Ranchero 500 is powered by a robust 302 V8 engine, paired with a smooth C4 automatic transmission. This combination delivers a driving experience that is both powerful and effortless. The Ranchero's engineering is further enhanced by features such as power brakes and power steering, ensuring responsive handling and control at every turn. Inside, the Ranchero offers a range of amenities; the air conditioning provides a refreshing environment, while the am/fm radio keeps you entertained on every journey. The cruise control allows for relaxed long-distance drives, and the tilt steering wheel can...

New Arrival Today

1988 Chevrolet Corvette Grand Sport

This Granite Metallic, with Light Brown Leather interior, 1988 Corvette Grand Sport is powered by a 5.7 Tune Port V8 engine with a 700R4 Automatic transmission.

$19,000

2537-CHI

6 Views

New Arrival

1985 Buick Riviera

This Gray, with Gray interior, 1985 Riviera is powered by a 5.0 LTR V8 engine with a 4-Speed Overdrive Automatic transmission.

$16,500

2541-CHI

8 Views

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1966 Ford Mustang

Fastback

This White With Blue Stripes, with White/Blue interior, 1966 Mustang is powered by a 331 V8 engine with an Automatic transmission.

$177,000

2325R-CHI

434 Views

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Chicago

1970 Dodge Charger RT

This Sub Lime Green, with Black interior, 1970 Charger RT is powered by a V8 528 HEMI, 581 DYER'S Blower engine with a 3-Speed Automatic transmission.

$163,000

2398-CHI

163 Views

Chicago

1937 Ford Slantback

Sedan Street Rod

This Ppg 6228 Orange Crush, with White interior, 1937 Slantback is powered by a Gm ZZ4 Crate V8 engine with a 700R4 Stall Converter Automatic transmission.

$100,000

2189-CHI

876 Views

Chicago

1954 Chevrolet Corvette

This White, with Red interior, 1954 Corvette is powered by a I6 engine with an Automatic transmission.

$99,000

2381-CHI

206 Views

Chicago

1937 Ford Replica

Coupe

This Burnt Orange/ Black, with Cream interior, 1937 Replica is powered by a ZZ4 350 Crate V8 engine with a 4-Speed Automatic transmission.

$99,000

2441-CHI

147 Views

Chicago

1970 Oldsmobile 442

Convertible

This White /Black Stripes, with Black interior, 1970 442 is powered by a 455 V8 engine with a 4-Speed Manual transmission.

$99,000

2484-CHI

231 Views

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Looking to sell your classic or exotic car? Let Gateway Classic Cars make the process safe and hassle free. All of our vehicles are situated in one of our 21 indoor showrooms.

Chicago

1964 Buick Riviera

This Marlin Blue, with Blue interior, 1964 Riviera is powered by a 425 Wildcat V8 engine with a 3-Speed Automatic transmission.

$89,000

2445-CHI

185 Views

Chicago

1962 Chevrolet Impala

Convertible

This Maroon , with Black interior, 1962 Impala is powered by a 409 V8 engine with a 4-Speed Manual transmission.

$89,000

2490-CHI

168 Views

Chicago

1963 Chevrolet Impala

This Tiel Green, with White interior, 1963 Impala is powered by a 409 V8 engine with a 4-Speed Manual transmission.

$83,000

2473-CHI

268 Views

Chicago

1938 LaSalle Series 50

4 Door Convertible

This Beige/ Black Convertible Top, with Red interior, 1938 Series 50 is powered by a Flat Head V8 engine with a 3-Speed On Column Manual transmission.

$80,000

2346-CHI

132 Views

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2021 Chevrolet Corvette Stingray

2LT

This Dark Shadow Gray Metallic, with Jet Black/Adrenaline Red interior, 2021 Corvette Stingray is powered by a 6.2 LTR V8 engine with a 8-Speed Dual Clutch Automatic transmission.

$77,000

2368R-CHI

202 Views

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Check Out Our Selection of Custom Apparel

Perfect for car enthusiasts! Sport one of these soft-style custom t-shirts at your favorite car cruise.

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1974 Dodge Challenger

440

This Sciaena Poly Red , with Black interior, 1974 Challenger is powered by a 440 V8 engine with a Manual transmission.

$77,000

2369R-CHI

391 Views

Chicago

1933 Plymouth Coupe

This Black, with Burgundy interior, 1933 Coupe is powered by a V8 engine with an Automatic transmission.

$76,000

2314-CHI

276 Views

Chicago

1941 Ford Sedan Delivery

This Lime Green, with Tan interior, 1941 Sedan Delivery is powered by a 350 V8 engine with a 3-Speed Automatic transmission.

$70,000

2487-CHI

103 Views

Chicago

1950 Ford Deluxe / Super Deluxe

Convertible

This Maroon Pearl, with Black/Tan interior, 1950 Deluxe / Super Deluxe is powered by a Olds 350 V8 engine with an Automatic transmission.

$70,000

2442-CHI

108 Views

Chicago

1968 Pontiac GTO

Convertible

This Red, with Off White interior, 1968 GTO is powered by a 400 V8 engine with a 3-Speed Automatic transmission.

$69,000

2415-CHI

181 Views

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Vintage Automobilia!

Check out our complete collection of vintage automobilia featuring this unique 'Racing With The Devil' sign. Easy to hang and perfect for any garage, workshop or man-cave!

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2010 Ford Mustang Shelby GT500

Convertible

This Blue With Red, with Black With Red interior, 2010 Mustang Shelby GT500 is powered by a Supercharged 5.4 LTR V8 engine with a 6-Speed Manual transmission.

$69,000

2375R-CHI

111 Views

Chicago

1978 Pontiac Firebird Trans-Am

This Gold, with Camel interior, 1978 Firebird Trans-Am is powered by a 455 V8 engine with a 4-Speed Manual transmission.

$66,000

2491-CHI

90 Views

Chicago

1970 Dodge Challenger

Convertible

This Burnt Orange , with Burnt Orange interior, 1970 Challenger is powered by a 318 V8 engine with a 704 Automatic transmission.

$66,000

2496-CHI

136 Views

Chicago

1969 Buick Gran Sport

This Copper Mist, with Black interior, 1969 Gran Sport is powered by a 455 V8 engine with a 3-Speed Automatic transmission.

$63,000

2419-CHI

233 Views

Chicago

2010 Ford F-150 SVT Raptor

This Molten Orange, with Black And Molten Orange interior, 2010 F-150 SVT Raptor is powered by a 5.4 LTR V8 engine with a 6-Speed Automatic transmission.

$63,000

2480-CHI

150 Views

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Vehicle Enthusiast Gift

The perfect gift for any gearhead! Surprise that special person in your life with a gift card for Gateway Classic Collectibles. Multiple Denominations Available

Chicago

1967 Chevrolet Nova

This Red, with Black interior, 1967 Nova is powered by a 383 V8 engine with a Turbo 350 Automatic transmission.

$57,000

2474-CHI

161 Views

Chicago

1969 Chevrolet Camaro

This Purple, with Black interior, 1969 Camaro is powered by a 572 Steve Morris V8 11:1 Compression engine with an Automatic Turbo 400 transmission.

$57,000

2405-CHI

317 Views

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