Classic Cars For Sale In Chicago

127 Vehicles For Purchase

127 Vehicles For Purchase

CHICAGO - INVENTORY

See for yourself! This sleek 1931 Ford Phaeton Replica Convertible For Sale is equipped with a 4 Cylinder and a 3 Speed Manual and is ready to hit the road for just $15,000 ~ Call Us Today! Read More...

5,353 VIEWS

4 FOLLOWERS

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CHICAGO - INVENTORY

Spectacular Red 1932 Chevrolet Sedan 2 Door Restomod For Sale boasts a 355 CID V8 engine ~ Listed at $33,500 is a real head turner ~ Call Us Today! Read More...

1,731 VIEWS

1 FOLLOWERS

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#1576-CHI

$45,000

CHICAGO - INVENTORY

Splendid classic! Our 1936 Ford Sedan For Sale complete with 350 CID V8 and 3 Speed Automatic can be yours today for $45,000 ~ Call Us Today! Read More...

1,700 VIEWS

1 FOLLOWERS

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CHICAGO - INVENTORY

Fascinating Red 1939 Ford Deluxe Vintage Air For Sale has a solid 350 CID V8 under the hood and a Automatic transmission ~ Call Us Today! Read More...

2,929 VIEWS

2 FOLLOWERS

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CHICAGO - INVENTORY

Fabulous 1940 Chevrolet Master Deluxe Restomod For Sale classic boasts a 4 Speed Automatic and 5.3l LS V8 ~ This head-turner is available today for only $45,000 ~ Call Us Today! Read More...

401 VIEWS

1 FOLLOWERS

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CHICAGO - INVENTORY

See for yourself! This sleek 1941 Crosley Station Wagon For Sale is equipped with a 4-cyl OHC and a 3 Speed Auto and is ready to hit the road for just $14,000 ~ Call Us Today! Read More...

2,278 VIEWS

1 FOLLOWERS

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CHICAGO - INVENTORY

See for yourself! This sleek 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 $46,500 ~ Call Us Today! Read More...

1,797 VIEWS

3 FOLLOWERS

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#1585-CHI

$8,000

CHICAGO - INVENTORY

A collector’s dream, this 1949 Cushman Scooter For Sale with a heart pounding 50 CC is complete with a 2 Speed Automatic for $8,000 ~ Call Us Today! Read More...

2,235 VIEWS

0 FOLLOWERS

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CHICAGO - INVENTORY

See for yourself! This sleek 1951 Ford F1 Restored Pickup Truck For Sale is equipped with a 239 Flathead V8 and a 3 Speed Manual and is ready to hit the road for just $29,500 ~ Call Us Today! Read More...

1,016 VIEWS

2 FOLLOWERS

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#1470-CHI

$19,500

CHICAGO - INVENTORY

Wonderful 1952 MG TD Convertible For Sale classic boasts a 4 Speed Manual and Inline 4 ~ This head-turner is available today for only $19,500 ~ Call Us Today! Read More...

3,640 VIEWS

2 FOLLOWERS

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#1703-CHI

$8,000

CHICAGO - SOLD

Fascinating Blue & Orange 1954 Ford Anglia For Sale has a solid 327 CI V8 under the hood and a TH350 transmission ~ Call Us Today! Read More...

2,498 VIEWS

2 FOLLOWERS

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CHICAGO - INVENTORY

Magnificent 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 ~ Call Us Today! Read More...

2,842 VIEWS

2 FOLLOWERS

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CHICAGO - INVENTORY

See for yourself! This sleek 1956 Ford Customline Restomod For Sale is equipped with a 302 CID V8 and a C6 Automatic and is ready to hit the road for just $77,500 ~ Call Us Today! Read More...

4,444 VIEWS

3 FOLLOWERS

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CHICAGO - INVENTORY

Wonderful Black 1956 Ford Customline Restomod For Sale ~ Listed for only $24,500, this 3 Speed Automatic transmission is the perfect complement to it’s 292 V8 engine ~ Call Us Today! Read More...

2,503 VIEWS

5 FOLLOWERS

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CHICAGO - INVENTORY

Fantastic classic! Our 1957 Chevrolet Bel Air Convertible For Sale complete with 283 CID V8 and 3 Speed Manual can be yours today for $83,000 ~ Call Us Today! Read More...

3,542 VIEWS

5 FOLLOWERS

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CHICAGO - INVENTORY

Striking Matador Red 1957 Chevrolet Bel Air Convertible For Sale boasts a 283 V8 engine ~ Listed at $64,500 is a real head turner ~ Call Us Today! Read More...

1,857 VIEWS

3 FOLLOWERS

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#1672-CHI

$29,500

CHICAGO - INVENTORY

See for yourself! This sleek 1957 Oldsmobile Super 88 For Sale is equipped with a 371 Cid V8 and a 3 Speed Auto and is ready to hit the road for just $29,500 ~ Call Us Today! Read More...

1,638 VIEWS

1 FOLLOWERS

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CHICAGO - SOLD

A collector’s dream, this 1957 Ford Thunderbird Convertible For Sale with a heart pounding 312 CID V8 is complete with a Automatic for $31,000 ~ Call Us Today! Read More...

8,989 VIEWS

6 FOLLOWERS

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CHICAGO - INVENTORY

Dramatic 1961 Ford Thunderbird Hardtop For Sale classic boasts a 3 Speed Auto and 390 CID V8 ~ This head-turner is available today for only $18,500 ~ Call Us Today! Read More...

2,279 VIEWS

2 FOLLOWERS

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CHICAGO - INVENTORY

Sensational Black 1962 Pontiac Catalina Bubble Top Mickey Thompson Big Block For Sale ~ Listed for only $87,000, this 4 Speed Manual transmission is the perfect complement to it’s 389 CID V-8 engine ~ Call Us Today! Read More...

2,927 VIEWS

2 FOLLOWERS

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#1735-CHI

$77,500

CHICAGO - INVENTORY

Sensational Red 1962 Chevrolet Corvette For Sale ~ Priced at $77,500, this 4 Speed transmission is the perfect complement to it’s 327 small block V8 engine ~ Call Us Today! Read More...

2,520 VIEWS

3 FOLLOWERS

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CHICAGO - INVENTORY

Grand Blue 1963 Chevrolet Nova II Dart Block Race For Sale ~ Priced at $25,000, this TH400 Auto transmission is the perfect complement to it’s 350 CID V8 Dart Block engine ~ Call Us Today! Read More...

2,174 VIEWS

0 FOLLOWERS

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#1488-CHI

$23,000

CHICAGO - INVENTORY

Wonderful White 1963 Buick Riviera For Sale boasts a 401 CID V8 Nailhead engine ~ Listed at $23,000 is a real head turner ~ Call Us Today! Read More...

10,643 VIEWS

9 FOLLOWERS

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#1691-CHI

$21,000

CHICAGO - INVENTORY

Grand Champagne 1963 Ford Galaxie For Sale boasts a 302 CID engine ~ Listed at $21,000 is a real head turner ~ Call Us Today! Read More...

3,839 VIEWS

6 FOLLOWERS

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CHICAGO - INVENTORY

See for yourself! This sleek 1964 Pontiac GTO V-8 Big Block For Sale is equipped with a V-8 and a 4 Speed Manual and is ready to hit the road for just $51,500 ~ Call Us Today! Read More...

2,812 VIEWS

1 FOLLOWERS

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Sell My Classic/Exotic Car

CHICAGO - INVENTORY

See for yourself! This sleek 1964 Chevrolet Malibu Convertible For Sale is equipped with a 327 CI V8 and a 4 Speed Manual and is ready to hit the road for just $33,500 ~ Call Us Today! Read More...

1,132 VIEWS

4 FOLLOWERS

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CHICAGO - INVENTORY

Magnificent classic! Our 1964 Chevrolet Corvair monza convertible For Sale complete with 110 Flat 6 and 4 Speed Manual can be yours today for $14,000 ~ Call Us Today! Read More...

2,225 VIEWS

3 FOLLOWERS

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CHICAGO - INVENTORY

Fascinating 1965 Shelby Cobra Factory-Five Racing For Sale classic boasts a 5 Speed Manual and 302 CID V8 ~ This head-turner is available today for only $49,000 ~ Call Us Today! Read More...

2,467 VIEWS

4 FOLLOWERS

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CHICAGO - INVENTORY

Awesome Yellow 1965 Ford Mustang 1964.5 Convertible For Sale boasts a 289 CI V8 engine ~ Listed at $32,000 is a real head turner ~ Call Us Today! Read More...

1,592 VIEWS

4 FOLLOWERS

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#1666-CHI

$29,000

CHICAGO - INVENTORY

Astonishing Black 1965 Chevrolet Chevelle For Sale has a solid 350 CID V8 under the hood and a 3 Speed Automatic transmission ~ Call Us Today! Read More...

936 VIEWS

2 FOLLOWERS

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Our Chicago Showroom proudly offers these amazing classic cars. Whether you are looking for a roadster or a stylish convertible, we have the car that you are looking for. Please enjoy browsing through our current inventory of 127 classic and exotic cars. When you find the one you are looking for, we are here to answer any additional questions you may have. We can assist with classic car financing and vehicle shipping to anywhere in the world. Visited us before? Please check out our growing list of new arrivals. You may also sign up here to receive a weekly email about our inventory. Classic cars are a solid investment that will surely turn heads at every corner. Do you have a classic car that you are interested in selling? One of our consignment concierge specialists will answer any questions you may have.

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

3,575 Classic and Exotics For Sale Today

Our vehicles were viewed 3,249,902 times in Jan 2020