Classic Cars For Sale In Chicago

66 Classics To Choose From


1939 LaSalle 50

Color: Burgundy
Transmission: 3 speed manual
Engine: 322 Cubic Inch V8


1948 Chevrolet Coupe

Color: Magenta/ Silver
Transmission: 3 speed automatic
Engine: 350 CID V8


1949 Oldsmobile 88 2S Restomod

Color: Burgundy
Transmission: Overdrive 700 R4 Automatic
Engine: 350 Chevy V8


1951 Ford Business Coupe

Color: Burgundy
Transmission: 2 speed automatic
Engine: Flat Head V8


1955 Ford Thunderbird

Color: Red
Transmission: Automatic
Engine: 292 CI V8

New Arrival

1958 Chevrolet Corvette

Color: Silver Blue
Transmission: 4-speed Manual
Engine: 283 cubic inch dual quad V8


1959 Chevrolet Apache

Color: Silver Metallic
Transmission: 700R4 4-speed Automatic
Engine: 454 CID V8


1963 Chevrolet Impala Station Wagon

Color: White & Gold
Transmission: 700 R4 Automatic
Engine: V8 V8


1965 Buick Riviera

Color: Burgundy
Transmission: 3-speed Automatic
Engine: 425 CID Nailhead V8


1965 Ford Thunderbird

Color: Black
Transmission: Automatic
Engine: 390 V8


1965 Pontiac GTO

Color: Turquoise
Transmission: 4 speed Manual
Engine: V8


1965 AMC Rambler

Color: White
Transmission: 3 speed automatic
Engine: 327 Cubic Inch V8


1967 Pontiac Firebird Convertible

Color: Red
Transmission: 5 Speed Manual
Engine: 400 cu V8


1968 Volkswagen Beetle

Color: Blue/flames
Transmission: 4-speed manual
Engine: Flat-4 cylinder engine


1969 Ford Cobra Replica

Color: Blue/ White
Transmission: 5 speed manual
Engine: 351 Cubic Inch V8


1970 Pontiac Grand Prix

Color: Black
Transmission: Automatic
Engine: 400 Cu In V8


1978 Chevrolet Camaro

Color: Orange
Transmission: 3 Speed Automatic
Engine: V8


1978 Chevrolet Corvette Indy Pace Car

Color: Blac/Silver
Transmission: 700R4 4-speed Automatic
Engine: 350 CID V8


1978 Mercedes-Benz 450SL

Color: silver
Transmission: automatic
Engine: v8


1980 Chevrolet Corvette

Color: Blue
Transmission: 4 speed Manual
Engine: 350 V8


1980 Rolls Royce SIlver Shadow II

Color: Gold/Brown
Transmission: Au
Engine: 6.75l V8


1983 Chevrolet Camaro Z-28

Color: Red
Transmission: Manual
Engine: 305 V8


1983 Buick Riviera

Color: maroon
Transmission: Automatic
Engine: 307 V8


1984 Chevrolet Corvette

Color: White
Transmission: Automatic
Engine: 350 cu V8


1984 Chevrolet Corvette C4

Color: Gold Metallic
Transmission: 4 speed Automatic
Engine: Crossfire Fuel Injection L83 V8


1985 AC Cobra Mark 4

Color: Blue with white stripe
Transmission: tremec 5 speed race transmission Manual
Engine: 351 Cleveland bored to 357 V8


1985 Mercedes-Benz 380 SL

Color: Champagne Metallic
Transmission: Automatic
Engine: 3.8l V8


1986 Chevrolet Monte Carlo SS

Color: White
Transmission: Automatic
Engine: 305 CID V8


1986 Mercedes-Benz 560SL Convertible

Color: Cabernet Red
Transmission: 4-speed Automatic
Engine: 5549cc V8


1988 Chevrolet Corvette

Color: black
Transmission: Automatic
Engine: 383 Stroker V8

Classic Cars For Sale In Chicago

Looking To Sell Your Vehicle?

Tens of thousands of individuals have trusted Gateway Classic Cars to sell their vehicles.

Consign And Sell Your Vehicle Today

Wonderful place for car guys.

Stephen Lavooi Buyer

Cool rides! Son loves this place!

Matt S. Other

I work as a car shipper all over the US and internationally. We have worked with Gateway Classic Cars for years and Kevin is by far one of the most trustworthy gentlemen in sales I have ever worked with. He cares for his clients like family and will surely take care of you honestly in any and every transaction! Every client I have spoke with that have interacted with him consider him one of the nicest people they have ever done business with.

Ethan K. Seller

If you're looking for the perfect vintage BMW, stop in the Atlanta showroom and ask for Brent V.! He's knowledgeable, friendly, and eager to make your dreams come true. I love my 1988 BMW e28 - thanks Brent!

Laurie V. Other

My thanks to Sal and the entire Gateway team for their work in locating, evaluating, completing a transaction and arranging the delivery of my 1954 Corvette. At every step in the process they were informative, responsive and consistently honest and objective in representing the car. Follow up after the sale for delivery and documentation was outstanding. This is a great organization, both in Fairmont City and Charlotte.

John Zei - Chicago, IL Buyer

Gateway Classic Cars is always a fun trip. They have really cool old muscle cars and trucks as well as some race cars.-STL

Jon Other

I have been very satisfied for that car, Mercury Marquis. Last week we had a Hot Wheels Show here in Finland and we got the 1st prize in Classic Car serie. The car is GREAT!!!! The car is 100% original like Sal said! I dont used an appraiser or inspector because I had a lot of pictures about this car and that was enough for me. The service was great. Everything was like we were agreed. Now I'll wait for the next car from Gateway Classic Car. I want something special and Sal is going to find it? Yes, I can say that everything was better than welldone! In my opinion You can trust for Gateway Classic Car Company!!!

Jori Rintam'ki - Finland Buyer

Bill & I really appreciate the way you handled the sale of our '49 Ford & our '33 Ford Roadster. We can't believe how quickly they sold & how very easy you are to do business with. Your website is very professional & it showed with the interest in our cars! Everything was handled so efficiently! And we were able to make what we wanted to on each sale! You were so very easy to work with, we will recommend you to anyone who asks, believe me! Thank you SO much for everything!

Bill & Judy Schrader Seller

I would like to express my experience in buying my first car from Sal at Gateway. I bought a Nice ElCamino and the very evening that I brought it home I had the trans. pump go out and it was several months before I could get it repaired, but Sal was good to his word he said he would work with me and when it was done He was there for me.

Robert Matrisch - Springfield, IL Buyer

What an excellent place to visit if you love cars. The Staff is very helpful and will answer all your questions. They're walking the floor the whole time. I will purchase a few cars in the very near future. Some vehicles aren't for sale. Must see!!!-ATL

Brian Other

Haven't visited the showroom yet.But talked to Duke,he answered all my questions.He informed me about upcoming events.Looking forward to visiting and I know y'all will give the other local classic car dealerships a run for their money. Time to play with the big boys.

Jesus Other

Smooth transaction and great communication throughout. Scott made the whole process very easy. Gateway has a great network of shipping contacts too, and provided several qoutes to pick from.

DD S, Buyer

A place most of us can dream of owning an amazing, beautiful car or truck!! Some vintage, some newer. Love going to Gateway and checking them out often. So many great vehicles to check out!!

Sharon F. Buyer

Must see. Check them out!!!

Michael Other

Love this place, amazing cars.. most of the cars were already sold... So that's a plus for people interested in selling with this establishment,

David G. Seller

My boyfriend's cousin, celebrated ???? ???? his 50th/retirement party @ Gateway Classic Cars on yesterday!!! It was fabulous!!! The showcase of all the classic cars ???? on the showcase floor was beautiful!!!! The decor ???? they had for his birthday/retirement was on point ???? I really loved ???? this and had a fabulous time, he had a dj, photo booth, balloons, candy ???? bar!!! Lounge chairs, cozy chairs, love seats!!! If your thinking about having a party ???? for your birthday, retirement, anniversary or for whatever reason ???? I recommend this place!!! We had a ball!!!

Rita W. Other

These guys are the best. Once I finally made the decision to sell my car, there was no question who I would trust that to. Thanks for a great job!

Ray Z. Seller

Bought a 1968 pontiac firebird here. Happy with the service

Damien Buyer

Duke was very helpful and help make sure that i was happy with the purchase of my 1985 monte carlo. Thanks Gateway and Duke I highly recommend if your looking to buy or sale a classic car.

Craig P. Buyer

I stopped in and was impressed. Brent was very knowledgeable and answered all my questions. I was extremely appreciative of the time he took with me. By the way the car is great!

Ben L. Buyer

This is a wonderful place to visit. It's a museum and also a place where you can purchase anyone of those vehicles on display.

Efrain D. Seller

...I'm having fun with this car. Thank you for the experience allowing me to come up and get it. Everyone who sees this car turns their heads. It's absolutely awesome...Every car has it's issues and that's just the way getting a classic 36 years old is. You were right and honest the whole time. A buyer has to weight the want vs. the output to decide and buy. I got what I wanted that was definitely not available anywhere in this area (El Paso Desert Southwest Area).

Scott Buyer

The family had a blast there and enjoyed it with all the vehicles and food from the areas. We had 2 3 year olds and really loved it there. Thank you will be back in time lol maybe looking at a wedding venue. Great time and awesome vehicles.

Tammy W. Other

I just wanted to pass along to other car enthusiasts that my experience with Gateway Classic Cars was a good one. Damon, Tyler, Ben and Mason along with the rest of the team at GCC were professional, and very knowledgeable about their cars. It’s definitely the best way to get your car noticed by thousands of people.

Daniel Sellers Seller

Hey Brad ! Thanks. I really do appreciate your effort. Good customer service is quickly becoming extinct in this day and age. I certainly will direct all my friends that dabble in vintage vehicles/hotrods/muscle cars to look you up!

Mike - Louisville, CO Buyer

These guys really did a great job for me! Jeff, Duke, and the whole team managed to sell five of my classic cars, even during Covid-19! A big thanks to them all!

David Robinson Seller

Highly recommend the Scottsdale Gateway Classics location to consign your vehicle. Tim and AL made me feel like my vehicle was the most important vehicle in their showroom.

Richard L. Seller

Brent was great helping us at the Atlanta Georgia showroom. Really good guy, knows his cars. while we didn't make a purchase on this visit, we'll deal with Brent again if a car that interest us shows up in the Atlanta showroom. Thanks Brent.

Jim W. Buyer

I recently bought a 1971 Dodge Charger from the Gateway Classic Cars Dealership in Milwaukee and was assisted by their representative Zach . I was an out of state buyer and their multi pictures and video of this car were outstanding and allowed me to make the decision to buy it sight unseen. I wanted to pass the word that for me it was a very pleasurable experience and I received a beautiful car. Thank you Zach and your team.

Larry Koerwer Buyer

A great squad to work with - the relationship doesn’t end after the sale - Cody & team go above and beyond to take care of their customers. Glad i came across these guys!!!

Jim L. Buyer

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Rel. August 9, 2022