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Classic Cars For Sale In Chicago

108 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.

CHICAGO - CALL FOR AVAILABILITY

Daring Red 1931 Ford Phaeton Replica Convertible For Sale boasts a 4 Cylinder engine with 3 Speed Manual transmission ~ Listed at $14,000 is a real head turner ~ Read More...

7,909 VIEWS

5 FOLLOWERS

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CATEGORIES: Convertible

CHICAGO - CALL FOR AVAILABILITY

Dramatic Red 1932 Chevrolet Sedan 2 Door Restomod For Sale ~ Listed at $33,500, this 4 Speed Auto transmission is the perfect complement to it’s 355 CID V8 engine ~ Read More...

4,145 VIEWS

3 FOLLOWERS

CATEGORIES: Restomod

#1576-CHI

$38,500

CHICAGO - INVENTORY

Wonderful Green 1936 Ford Sedan For Sale classic boasts a 3 Speed Automatic and 350 CID V8 ~ This head-turner is available today for only $38,500 ~ Read More...

2,804 VIEWS

2 FOLLOWERS

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CHICAGO - INVENTORY

Eye-catching classic! Our Red 1939 Ford Deluxe Vintage Air For Sale complete with 350 CID V8 and Automatic can be yours today for $57,500 ~ Read More...

3,752 VIEWS

3 FOLLOWERS

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CHICAGO - INVENTORY

Spectacular Burnt Orange 1940 Chevrolet Master Deluxe Restomod For Sale boasts a 5.3l LS V8 engine with 4 Speed Automatic transmission ~ Listed at $42,500 is a real head turner ~ Read More...

1,652 VIEWS

1 FOLLOWERS

CATEGORIES: Restomod

CHICAGO - SOLD

Fascinating Red 1941 Crosley Station Wagon For Sale boasts a 4-cyl OHC engine with 3 Speed Auto transmission ~ Listed at $11,500 is a real head turner ~ Read More...

4,678 VIEWS

2 FOLLOWERS

CATEGORIES: Wagon

CHICAGO - INVENTORY

Wonderful Fuchsia 1949 Lincoln Cosmopolitan Restomod For Sale has a solid 350 CID V8 under the hood and a 3 Speed Auto transmission ~ Read More...

4,293 VIEWS

6 FOLLOWERS

CATEGORIES: Restomod

#1585-CHI

$7,500

CHICAGO - INVENTORY

Sensational Red 1949 Cushman Scooter For Sale boasts a 50 CC engine with 2 Speed Automatic transmission ~ Listed at $7,500 is a real head turner ~ Read More...

3,962 VIEWS

1 FOLLOWERS

CATEGORIES: Motorcycle

CHICAGO - INVENTORY

Check out this gorgeous Red 1951 Ford F1 Restored Pickup Truck For Sale classic boasts a 3 Speed Manual and 239 Flathead V8 ~ This head-turner is available today for only $29,500 ~ Read More...

3,014 VIEWS

1 FOLLOWERS

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CATEGORIES: Truck

#1755-CHI

$51,500

CHICAGO - INVENTORY

Wonderful classic! Our Teal and White 1955 Chevrolet Bel Air For Sale complete with 265 CID V8 and 700R4 4 Speed Automatic can be yours today for $51,500 ~ Read More...

2,357 VIEWS

4 FOLLOWERS

CHICAGO - INVENTORY

Fabulous White and Red 1955 Ford Fairlane Victoria Fordomatic For Sale ~ Listed at $32,000, this 3 Speed Automatic transmission is the perfect complement to it’s 272 CID V8 engine ~ Read More...

4,417 VIEWS

3 FOLLOWERS

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CHICAGO - SOLD

See for yourself! This sleek Black 1956 Ford Customline Restomod For Sale is equipped with a 292 V8 and a 3 Speed Automatic and is ready to hit the road for just $24,500 ~ Read More...

4,815 VIEWS

6 FOLLOWERS

CATEGORIES: Restomod

CHICAGO - CALL FOR AVAILABILITY

Daring Turquoise 1957 Chevrolet Bel Air Convertible For Sale ~ Listed at $83,000, this 3 Speed Manual transmission is the perfect complement to it’s 283 CID V8 engine ~ Read More...

5,357 VIEWS

8 FOLLOWERS

CATEGORIES: Convertible

CHICAGO - SOLD

Wonderful classic! Our Dark Blue 1957 Pontiac Star Chief Station Wagon For Sale complete with V8 and Automatic can be yours today for $16,000 ~ Read More...

3,601 VIEWS

2 FOLLOWERS

CATEGORIES: Wagon

CHICAGO - INVENTORY

Unbelievable White 1961 Ford Thunderbird Hardtop For Sale has a solid 390 CID V8 under the hood and a 3 Speed Auto transmission ~ Read More...

4,462 VIEWS

4 FOLLOWERS

CHICAGO - INVENTORY

Prodigious Yellow and Black 1961 Volkswagen Dune Buggy Convertible For Sale boasts a 1600 cc Flat 4 engine with 4 Speed Manual transmission ~ Listed at $18,500 is a real head turner ~ Read More...

2,741 VIEWS

1 FOLLOWERS

CATEGORIES: Convertible

CHICAGO - INVENTORY

A collector’s dream, this Black 1962 Pontiac Catalina Bubble Top "Mickeys Magic Motor" For Sale with a heart pounding 389 CID V-8 is complete with a 4 Speed Manual for $87,000 ~ Read More...

4,809 VIEWS

2 FOLLOWERS

#1735-CHI

$77,500

CHICAGO - INVENTORY

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

5,716 VIEWS

6 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...

1,584 VIEWS

4 FOLLOWERS

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#1761-CHI

$27,000

CHICAGO - INVENTORY

Wonderful Off White 1963 Pontiac Grand Prix For Sale ~ Listed at $27,000, this 3 Speed Automatic transmission is the perfect complement to it’s 389 CI V8 engine ~ Read More...

879 VIEWS

1 FOLLOWERS

#1488-CHI

$23,000

CHICAGO - INVENTORY

See for yourself! This sleek White 1963 Buick Riviera For Sale is equipped with a 401 CID V8 Nailhead and a 3 Speed Automatic and is ready to hit the road for just $23,000 ~ Read More...

14,777 VIEWS

15 FOLLOWERS

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CHICAGO - SOLD

A collector’s dream, this Blue 1963 Chevrolet Nova II Dart Block Race For Sale with a heart pounding 350 CID V8 Dart Block is complete with a TH400 Auto for $24,000 ~ Read More...

5,165 VIEWS

2 FOLLOWERS

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CATEGORIES: Race CarMuscle Car

#1691-CHI

$21,000

CHICAGO - SOLD

Incredible classic! Our Champagne 1963 Ford Galaxie For Sale complete with 302 CID and Automatic can be yours today for $21,000 ~ Read More...

8,876 VIEWS

11 FOLLOWERS

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CHICAGO - INVENTORY

A collector’s dream, this Yellow 1964 Chevrolet Corvette Convertible For Sale with a heart pounding 327 CID V8 is complete with a 4 Speed Manual for $51,500 ~ Read More...

3,620 VIEWS

3 FOLLOWERS

CATEGORIES: ConvertibleSports Car

CHICAGO - INVENTORY

Unbelievable classic! Our Black 1964 Pontiac GTO V-8 Big Block For Sale complete with V-8 and 4 Speed Manual can be yours today for $50,500 ~ Read More...

5,013 VIEWS

1 FOLLOWERS

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Sell My Classic/Exotic Car

CHICAGO - SOLD

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

4,556 VIEWS

5 FOLLOWERS

CATEGORIES: Convertible

CHICAGO - CALL FOR AVAILABILITY

See for yourself! This sleek Yellow 1965 Ford Mustang 1964.5 Convertible For Sale is equipped with a 289 CI V8 and a 3 Speed Auto and is ready to hit the road for just $32,000 ~ Read More...

3,472 VIEWS

6 FOLLOWERS

QUICK VIEW

CATEGORIES: ConvertibleSports Car

#1666-CHI

$25,500

CHICAGO - SOLD

Remarkable classic! Our Black 1965 Chevrolet Chevelle For Sale complete with 350 CID V8 and 3 Speed Automatic can be yours today for $25,500 ~ Read More...

5,072 VIEWS

4 FOLLOWERS

CATEGORIES: Muscle Car

CHICAGO - INVENTORY

Fascinating White 1966 Buick Riviera 425 CI V8 Wildcat For Sale boasts a 425 CID V8 engine with 3 Speed Automatic transmission ~ Listed at $31,000 is a real head turner ~ Read More...

6,157 VIEWS

7 FOLLOWERS

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#1679R-CHI

$38,000

CHICAGO - CALL FOR AVAILABILITY

A collector’s dream, this White 1966 Chevrolet Nova II SS For Sale with a heart pounding 350 CID V8 is complete with a Automatic for $38,000 ~ Read More...

6,771 VIEWS

7 FOLLOWERS

QUICK VIEW

CATEGORIES: Muscle Car

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 108 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

3,328 Classic and Exotics For Sale Today

Our vehicles were viewed 4,713,874 times in Jun 2020