41.46457909999999 -87.57982349999999

Classic Cars and Trucks For Sale In Chicago

Find Your Dream Classic Here

127 Vehicles Found

1970 Dodge Charger

Experience the thrill of driving with this 1970 Dodge Charger R/T, a classic American muscle car that is sure to turn heads wherever you go. This beauty is dressed in a striking Rallye Green (EF6) exterior, a color that instantly commands attention and showcases its iconic design. Under its hood, the Charger R/T houses a beast - a 528 Hemi dyers 871 Blower V8 engine. This robust engine is paired with a 3-Speed automatic transmission that promises smooth gear changes and a powerful performance every time. Whether you're cruising down open highways or navigating tight city streets, this Charger R/T delivers an invigorating and exhilarating driving experience. Step inside the Charger R/T and be greeted by an all-black vinyl interior, an ode to the timeless styling...

New Arrival

1933 Plymouth Coupe

This vehicle is powered by a V8 engine with an Automatic transmission.

$79,000

2314-CHI

32 Views

Recent Arrival

1955 Chevrolet Bel Air

This Red/White, with Red?tan interior, 1955 2nd Gen Bel Air is powered by a 283 V8 engine with a 3-Speed Column Shift Manual transmission.

$53,000

2291-CHI

64 Views

Recent Arrival

1981 Jeep Scrambler

This vehicle is powered by a 4.2 L I6 engine with a 4-Speed Manual transmission.

$40,000

2315-CHI

38 Views

Advertisement

Sell Your Classic Safely And Smoothly!

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.

Recent Arrival

1946 Ford Coupe

This vehicle is powered by a 350 V8 engine with an Automatic transmission.

$36,000

2309-CHI

55 Views

New Arrival

1987 Mercedes-Benz 560SL

This vehicle is powered by a 5.6 L V8 engine with an Automatic transmission.

$33,000

2321-CHI

20 Views

Recent Arrival

1930 Ford Model A

Deluxe Roadster

This vehicle is powered by a 200.5 4 Cylinder engine with a 4-Speed Manual transmission.

$32,000

2313-CHI

33 Views

New Arrival

1975 Chevrolet Corvette

This Red, with Silver interior, 1975 C3 Corvette is powered by a 350 V8 engine with a Manual transmission.

$29,000

2317-CHI

30 Views

New Arrival

2012 BMW 650 I

This vehicle is powered by a 4.4 Liter Twin Turbo V8 engine with a 8-Speed Automatic transmission.

$28,000

2318-CHI

31 Views

Advertisement

Advertise Your Business Here!

Elevate your brand and showcase your products on our site. Millions of views every month!

New Arrival

1980 Chevrolet Corvette

This Red, with Black interior, 1980 C3 Corvette is powered by a 350 V8 engine with an Automatic transmission.

$27,000

2316-CHI

37 Views

Recent Arrival

1988 Chevrolet Camaro

RS Convertible

This Orange And Black, with Gray And Black interior, 1988 3rd Gen Camaro is powered by a 350 V8 engine with an Automatic transmission.

$24,000

2311-CHI

44 Views

1988 Chevrolet Camaro (2311-CHI)

For sale: a stunning 1988 Chevrolet Camaro RS Convertible, a standout model with its bold orange and black exterior. The stylish aesthetic extends to the interior with a classic gray and black cloth finish, offering a comfortable and appealing environment for both driver and passenger. Under the hood, this Camaro RS comes with a robust 350 V8 engine, coupled with a smooth automatic transmission, providing an exhilarating driving experience synonymous with the Chevrolet Camaro lineage. This vehicle is not just about looks and power - it is also fully-equipped with an array of key features for your comfort and convenience. Stay cool during those hot summer drives with the built-in air conditioning system and keep the entertainment alive with an AM/FM radio and CD player at...

Recent Arrival

1993 Toyota Pickup

This vehicle is powered by a 2.4 Liter 4 Cylinder engine with a Manual transmission.

$22,500

2308-CHI

52 Views

New Arrival

2011 Lincoln Town Car

Signature L

This vehicle is powered by a 4.6 Liter V8 engine with an Automatic transmission.

$22,000

2320-CHI

30 Views

Recent Arrival

1984 Chevrolet C20

Pickup

This vehicle is powered by a 350 CID V8 engine with an Automatic transmission.

$21,000

2095-CHI

564 Views

Advertisement

Weekly Online Auction

Click – Bid – Win – Drive! Our weekly classic car auction platform features the newest in the Gateway Classic Car inventory. Check out this week's auction - click now!

Recent Arrival

1985 Buick Riviera

This vehicle is powered by a V-8 V8 engine with an Automatic transmission.

$17,500

2290-CHI

88 Views

Recent Arrival

1999 BMW 328iC

This vehicle is powered by a 2.8 Liter I6 engine with a 5-Speed Manual transmission.

$16,500

2306-CHI

39 Views

Chicago

1970 Dodge Charger

RT

This Rallye Green (ef6), with Black interior, 1970 2nd Gen Charger is powered by a 528 Hemi Dyers 871 Blower V8 engine with a 3-Speed Automatic transmission.

$209,000

2279-CHI

374 Views

Chicago

1937 Ford Slantback

Sedan

This vehicle is powered by a Gm ZZ4 Crate V8 engine with a 700R4 Stall Converter Automatic transmission.

$120,000

2189-CHI

612 Views

Chicago

1965 Chevrolet Corvette

Convertible

This Rally Red, with Black interior, 1965 C2 Corvette is powered by a 350 CID V8 engine with a 4-Speed Manual transmission.

$109,000

2214-CHI

224 Views

Advertisement

Bid Today!

Each week Gateway Classic Cars features their newest inventory . Click the image above to see the latest classic and exotic vehicles available.

Chicago

1941 Willys Coupe

This vehicle is powered by a Sm Blk (GM) With Weiand Blower V8 engine with an Automatic transmission.

$99,000

2283-CHI

159 Views

Call For Availability

2013 Chevrolet Corvette

Convertible Custom

This Black, with Black interior, 2013 C6 Corvette is powered by a 6.2L V8 engine with a 6-Speed Automatic transmission.

$79,000

2165-CHI

865 Views

2013 Chevrolet Corvette (2165-CHI)

Under the hood is a peppy 6. 2L V8 sending power through a 6-speed automatic overdrive transmission to the rear wheels. This triple-black Corvette is accented by a collection of Custom blue lights scattered around the interior, exterior, engine bay, and trunk of this drop-top 'Vette. Additionally, a full aftermarket sound system has been fitted that turns this Corvette into a concert on wheels. The doors have been converted to a Lamborghini-style vertical-opening function. This Custom show-car is sure to turn heads anywhere you go. The massive carbon-fiber wing affixed to the trunk lid gives off a race-inspired vibe. The sun visors are fitted with 7' display screens connected to the GPS-enabled radio in...

Chicago

1969 AMC Rambler

This vehicle is powered by a 390 V8 engine with a 4-Speed Manual transmission.

$72,000

2292-CHI

136 Views

Chicago

1965 Factory Five Cobra

This vehicle is powered by a 306 Small Block Ford V8 engine with a 5-Speed Manual transmission.

$67,000

2199-CHI

537 Views

Chicago

1934 Ford 3 Window

This vehicle is powered by a 350 Chevy V8 engine with a Jeg 700 R 4 Automatic transmission.

$62,000

2240-CHI

470 Views

Advertisement

Calling All Car Clubs!

Our Featured Car Club Program helps car clubs raise their visibility in the market along with money for their organization. Contact us to learn more today!

Chicago

2010 Chevrolet Camaro

SS

This Black/Custom Flames , with Black interior, 2010 5th Gen Camaro is powered by a Procharged LS3 V8 engine with a 6-Speed Manual transmission.

$60,000

2205-CHI

295 Views

Chicago

1965 Chevrolet Chevelle

Malibu SS

This Metallic Red, with Tan and Gold interior, 1965 1st Gen Chevelle is powered by a 502 CID Crate V8 engine with a 4-Speed Manual transmission.

$60,000

2234-CHI

611 Views

Chicago

1960 Chevrolet Brookwood

Station Wagon

This vehicle is powered by a 6.2 L LSA V8 engine with a Tremec Supermag 6-Speed Manual transmission.

$59,000

2269-CHI

259 Views

Chicago

2011 Mercedes-Benz SL 63 AMG

This vehicle is powered by a 6.2 L V8 engine with an Automatic transmission.

$59,000

2299-CHI

82 Views

Call For Availability

1963 Chevrolet C10

This Red, with Black And Red interior, 1963 1st Gen C10 is powered by a 350 V8 engine with a 3-Speed Automatic transmission.

$58,000

2248-CHI

174 Views

Advertisement

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.

Chicago

1967 Chevrolet Nova

This Red/Blue Flames, with Blue/Red interior, 1967 2nd Gen Nova is powered by a 383 STROKER/ Dual Quads V8 engine with a 700 R4 Automatic transmission.

$57,000

2293-CHI

135 Views

Chicago

1967 Dodge Coronet

This Spinaker White/With A Touch Of Blue Pearl, with Black/Blue interior, 1967 5th Gen Coronet is powered by a 440 V8 engine with a 3-Speed 727 Tourque Flight Automatic transmission.

$55,000

2243-CHI

262 Views

1967 Dodge Coronet (2243-CHI)

Introducing the imposing 1967 Dodge Coronet that speaks volumes about your refined taste in classic vehicles. This esteemed automobile has been crafted in a gorgeous Spinaker White exterior, adding a touch of Blue Pearl, a combination that impeccably expresses both elegance and performance. The Coronet's luxurious interior is tastefully designed in a black and blue leather upholstery, creating a stylish and comfortable environment that brings out the nostalgia of the classic era while providing the comfort of modern luxury. Beneath its stunning exterior is a beastly 440 V8 engine that doesn't compromise on power or performance. It comes fully equipped with a 3-speed 727 Torque Flight automatic transmission, known for its smooth gear shifts and iconic performance. This 1967 Dodge Coronet stands on a set of...

Contact Us

Chicago Showroom

Please provide a first name.
Please provide a last name.
Please provide an email address.
Please provide a subject.
Please provide a message.
WARNING: Please do not upload private or confidential documents or files using this form.
Drag and drop here to upload
Allowed file types: JPG, PNG, GIF, PDF (max size: 10 MB)
You must agree before submitting.

Price Range

$ K
$ K

Year Range

Transmission

Colors

[ All | None ]

Settings

Vehicle Card Size
Alert