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Classic Cars For Sale In Chicago

93 Vehicles For Sale

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Please contact us at (866) 383-1416 to make an appointment if you are interested in buying or selling a vehicle.

#1806-CHI

$18,500

CHICAGO - SOLD

A collector’s dream, this Red 1929 Ford Model A For Sale with a heart pounding 200.5 CID I-4 is complete with a 3 Speed Manual for $18,500 ~ Read More...

1,873 VIEWS

1 FOLLOWERS

QUICK VIEW

CHICAGO - CALL FOR AVAILABILITY

Sensational Red 1931 Ford Phaeton Replica Convertible For Sale ~ Buy for $14,000, this 3 Speed Manual transmission is the perfect complement to it’s 4 Cylinder engine ~ Read More...

10,256 VIEWS

5 FOLLOWERS

QUICK VIEW

CATEGORIES: Convertible

#1576-CHI

$38,500

CHICAGO - INVENTORY

A collector’s dream, this Green 1936 Ford Sedan For Sale with a heart pounding 350 CID V8 is complete with a 3 Speed Automatic for $38,500 ~ Read More...

3,811 VIEWS

1 FOLLOWERS

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CHICAGO - INVENTORY

A collector’s dream, this Burnt Orange 1940 Chevrolet Master Deluxe Restomod For Sale with a heart pounding 5.3l LS V8 is complete with a 4 Speed Automatic for $40,000 ~ Read More...

3,007 VIEWS

1 FOLLOWERS

CATEGORIES: Restomod

CHICAGO - INVENTORY

See for yourself! This sleek Fuchsia 1949 Lincoln Cosmopolitan Restomod For Sale is equipped with a 350 CID V8 and a 3 Speed Auto and is ready to hit the road for just $40,000 ~ Read More...

6,450 VIEWS

7 FOLLOWERS

CATEGORIES: Restomod

#1585-CHI

$7,500

CHICAGO - INVENTORY

Fabulous classic! Our Red 1949 Cushman Scooter For Sale complete with 50 CC and 2 Speed Automatic can be yours today for $7,500 ~ Read More...

5,417 VIEWS

1 FOLLOWERS

CATEGORIES: Motorcycle

CHICAGO - INVENTORY

Unbelievable White 1954 Oldsmobile 98 Holiday For Sale classic boasts a 3 Speed Auto and 324 Cu In V8 ~ This head-turner is available today for only $29,500 ~ Read More...

1,824 VIEWS

1 FOLLOWERS

#1755-CHI

$51,500

CHICAGO - INVENTORY

See for yourself! This sleek Teal and White 1955 Chevrolet Bel Air For Sale is equipped with a 265 CID V8 and a 700R4 4 Speed Automatic and is ready to hit the road for just $51,500 ~ Read More...

3,755 VIEWS

4 FOLLOWERS

#1771-CHI

$44,500

CHICAGO - INVENTORY

See for yourself! This sleek Red / Cream White 1955 Chevrolet Bel Air For Sale is equipped with a 265 CID V8 and a 2 Speed Auto and is ready to hit the road for just $44,500 ~ Read More...

1,341 VIEWS

1 FOLLOWERS

#1790-CHI

$18,500

CHICAGO - INVENTORY

Fascinating Blue 1955 Ford Customline For Sale ~ Purchase for $18,500, this 2 Speed Auto transmission is the perfect complement to it’s 272 Cu In V8 Y-Bock engine ~ Read More...

1,792 VIEWS

1 FOLLOWERS

CHICAGO - CALL FOR AVAILABILITY

Fantastic White and Red 1955 Ford Fairlane Victoria Fordomatic For Sale has a solid 272 CID V8 under the hood and a 3 Speed Automatic transmission ~ Read More...

5,948 VIEWS

3 FOLLOWERS

QUICK VIEW

CHICAGO - INVENTORY

Amazing Red 1957 Chevrolet Bel Air Convertible Conv For Sale boasts a 283 V8 engine with 2 Speed Auto transmission ~ Listed at $71,000 is a real head turner ~ Read More...

315 VIEWS

0 FOLLOWERS

CATEGORIES: Convertible

#1786-CHI

$15,000

CHICAGO - SOLD

Magnificent Gold 1959 Volkswagen Citation For Sale classic boasts a 4 Speed Manual and 1600 CC ~ This head-turner is available today for only $15,000 ~ Read More...

1,562 VIEWS

1 FOLLOWERS

#1804-CHI

$88,500

CHICAGO - INVENTORY

Unbelievable Red 1961 Chevrolet Corvette For Sale ~ Listed for $88,500, this 4 Speed Manual transmission is the perfect complement to it’s 283 Cu IN V8 engine ~ Read More...

1,546 VIEWS

0 FOLLOWERS

CATEGORIES: Sports Car

CHICAGO - INVENTORY

A collector’s dream, this Yellow and Black 1961 Volkswagen Dune Buggy Convertible For Sale with a heart pounding 1600 cc Flat 4 is complete with a 4 Speed Manual for $18,500 ~ Read More...

4,879 VIEWS

3 FOLLOWERS

CATEGORIES: Convertible

#1735-CHI

$77,500

CHICAGO - INVENTORY

Sensational Red 1962 Chevrolet Corvette For Sale has a solid 327 small block V8 under the hood and a 4 Speed transmission ~ Read More...

7,964 VIEWS

7 FOLLOWERS

CHICAGO - CALL FOR AVAILABILITY

Incredible Black 1962 Pontiac Catalina Bubble Top For Sale ~ Listed for $85,000, this 4 Speed Manual transmission is the perfect complement to it’s 389 CID V-8 engine ~ Read More...

6,284 VIEWS

2 FOLLOWERS

#1758-CHI

$32,000

CHICAGO - INVENTORY

See for yourself! This sleek Wimbleton White Pearl 1963 Ford Galaxie For Sale is equipped with a 427 CID V8 and a 3 Speed Automatic and is ready to hit the road for just $32,000 ~ Read More...

4,439 VIEWS

4 FOLLOWERS

QUICK VIEW

#1761-CHI

$24,500

CHICAGO - INVENTORY

Wonderful Off White 1963 Pontiac Grand Prix For Sale ~ Buy for $24,500, this 3 Speed Automatic transmission is the perfect complement to it’s 389 CI V8 engine ~ Read More...

2,703 VIEWS

1 FOLLOWERS

#1488-CHI

$22,000

CHICAGO - INVENTORY

Astonishing classic! Our White 1963 Buick Riviera For Sale complete with 401 CID V8 Nailhead and 3 Speed Automatic can be yours today for $22,000 ~ Read More...

18,823 VIEWS

17 FOLLOWERS

QUICK VIEW

CHICAGO - INVENTORY

Dazzling Yellow 1964 Chevrolet Corvette Convertible For Sale ~ Listed for $48,000, this 4 Speed Manual transmission is the perfect complement to it’s 327 CID V8 engine ~ Read More...

5,684 VIEWS

6 FOLLOWERS

CATEGORIES: ConvertibleSports Car

#1795-CHI

$31,000

CHICAGO - INVENTORY

Grand Red 1964 Chevrolet Malibu For Sale ~ Listed at $31,000, this 4 Speed Manual transmission is the perfect complement to it’s 327 CID V8 engine ~ Read More...

1,806 VIEWS

2 FOLLOWERS

#1797-CHI

$28,500

CHICAGO - SOLD

Astonishing Black 1964 Buick Riviera For Sale has a solid 383 Cu In V8 under the hood and a 3 Speed Auto transmission ~ Read More...

2,862 VIEWS

3 FOLLOWERS

QUICK VIEW

#1805-CHI

$27,000

CHICAGO - INVENTORY

Astounding Black 1965 Ford Mustang For Sale classic boasts a 3 Speed Auto and 351 W V8 ~ This head-turner is available today for only $27,000 ~ Read More...

3,334 VIEWS

4 FOLLOWERS

QUICK VIEW

CATEGORIES: Sports Car

#1783-CHI

$33,500

CHICAGO - SOLD

Awesome classic! Our Red 1965 Chevrolet Impala For Sale complete with 396 Cu In V8 and 3 Speed Auto can be yours today for $33,500 ~ Read More...

1,925 VIEWS

0 FOLLOWERS

CATEGORIES: Muscle Car

CHICAGO - INVENTORY

Daring White 1966 Buick Riviera 425 CI V8 Wildcat For Sale classic boasts a 3 Speed Automatic and 425 CID V8 ~ This head-turner is available today for only $31,000 ~ Read More...

8,468 VIEWS

7 FOLLOWERS

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#1811-CHI

$24,500

CHICAGO - INVENTORY

Dramatic Wimbledon White 1966 Ford Mustang For Sale has a solid 302 CID V8 under the hood and a AOD 4 Speed automatic overdrive transmission ~ Read More...

2,680 VIEWS

2 FOLLOWERS

QUICK VIEW

CATEGORIES: Sports Car

CHICAGO - INVENTORY

Spectacular White 1967 Alfa Romeo Giulia Super For Sale boasts a 1570 CC Straight 4 engine with 5 Speed Manual transmission ~ Listed at $26,500 is a real head turner ~ Read More...

5,674 VIEWS

6 FOLLOWERS

#1773-CHI

$16,000

CHICAGO - INVENTORY

Fantastic Fawn Beige 1967 Mercury Cougar For Sale classic boasts a 3 Speed Automatic and 289 CID V8 200HP ~ This head-turner is available today for only $16,000 ~ Read More...

5,286 VIEWS

3 FOLLOWERS

QUICK VIEW

CATEGORIES: Muscle Car

#1781-CHI

$24,500

CHICAGO - SOLD

A collector’s dream, this Red 1967 Chevrolet Camaro For Sale with a heart pounding 327 Cu In V8 is complete with a 2 Speed Automatic for $24,500 ~ Read More...

5,191 VIEWS

10 FOLLOWERS

CATEGORIES: Sports CarMuscle Car

Turning the key and feeling the engine roar to life is what motivates classic car buyers all over the world. At Gateway Classic Cars of Chicago we have 93 amazing vehicles which are sure to take your breath away. Whether it’s a hot rod or maybe something from the roaring 20’s, Gateway Classic Cars has the classic or exotic car for you. Contact one of our inventory specialists today! Financing available for all qualified buyers.

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Our vehicles are published on several websites including ~ Autotrader Classics ~ Hemmings ~ ClassicCars ~ Carsforsale ~ AllCollectorCars ~ eBay ~ Facebook ~ YouTube

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Gateway Classic Cars
1237 Central Park Dr. O'Fallon, IL. 62269 | 618.271.3000 | 800.231.3616

3,121 Classic and Exotics For Sale Today

Our vehicles were viewed 7,750,729 times in Sep 2020