Reserve a Car
1935
Est. 1995  ·  Chicagoland

Chicago
VintageCharters

Since 1995, specializing in chauffeured motorcars

Avid vintage car restorers bringing excitement, comfort and style to your most cherished occasions and film production throughout the Midwest.

1935 Packard Twelve Club Sedan
1935 Packard 12-Cylinder Club Sedan
Bentley R Type
1962 Alfa Romeo
30+Years of Service
16Classic Motorcars
4thGeneration Family
Memories Created

Our Story

Third & Fourth
Generation
Restorers

✦ ✦ ✦

Chicago Vintage Charters has specialized in chauffeured motorcars — delivering excitement, comfort, and style for your most special occasions throughout the Midwest.

Our family's passion for motorcars is not merely a business — it is a calling passed through generations. Friendly and knowledgeable chauffeurs deliver exceptional vehicles for weddings, graduations, anniversaries, photography, film production, and Chicagoland guided tours.

Let our experienced staff cater to your special event with exceptional customer service. Our distinctive vehicles rekindle memories and generate new excitement for every occasion. Guided movie location and architectural tours are tailored to your needs.

The Team

John McNabola

"From my earliest years, I have had an insatiable fascination with cars, the remarkable history of motorcars and the joy and excitement they bring to persons of all ages." — Avid car enthusiast, writer, and restoration specialist.

Connor Harrington

Worked extensively in the restoration of vintage sports cars with Roadster Salon, Inc. Active member of the Classic Car Club of America. Both John and Connor have served as Geneva Concours d'Élégance judges and attended Pebble Beach, Meadowbrook, and CCCA Concours LeGrande.

Joseph Lynaugh

Joe is remarkably gifted with restoring and maintaining vintage cars. As a retired machinist and certified ASE mechanic, he coordinates the "tender, loving care" required for our vintage cars.

John McNabola
Chicago Vintage Charters history
John McNabola with a classic car
Joseph Lynaugh
💍Weddings

Arrive in timeless style on your most precious day

🎓Graduations

Celebrate achievement with a ride worth remembering

🎬Film & Photography

Period-correct vehicles for production excellence

🏛️Chicago Tours

Guided architectural & movie location tours

The Collection

Sensational
Motorcars

Fifteen meticulously restored classics — from pre-war American grand tourers to the finest European roadsters of the sixties. Each one a living, breathing piece of automotive history.

The Complete Collection
1966 Mercedes-Benz Cabriolet
MB
Photo
1966Mercedes-Benz Cabriolet
1941 Buick Convertible
Buick
Photo
1941Buick Convertible
1959 Porsche 356 Cabriolet
356
Photo
1959Porsche 356 Cabriolet
1982 Mercedes-Benz SL
SL
Photo
1982Mercedes-Benz SL
1967 Toronado Deluxe
Olds
Photo
1967Toronado Deluxe
1969 MG C Roadster
MG
Photo
1969MG 'C' Roadster
1955 Austin-Healey
AH
Photo
1955Austin-Healey
1940 Packard 110
1940Packard 110
1949 Triumph Rumbleseat Convertible
TR
Photo
1949Triumph Rumbleseat Convertible

A Century of Passion

The Trainor Legacy

— ✦ —

The First Trainor Motorcar

Our family passion for motorcars dates back to the first Trainor family car — an imposing 1912 Stoddard Dayton delivered with closed coachwork for harsh Chicago winters and a warm weather body. Description on photo from the late Edward Vincent Trainor (EVT).

1912 Stoddard Dayton — first Trainor motorcar

The Lincoln Automobile Company

Chicago's Motor Row was home to 116 carmakers with elaborate showrooms in architecturally significant buildings. Here is a picture of EVT's Lincoln Automobile Company showroom — at the heart of the golden age of American motoring.

Lincoln Automobile Company showroom on Motor Row

The Ed Trainor Special

E.V. and son Tully are pictured here with the Ed Trainor Special at the 1951 Indianapolis qualification trials. The Miller supercharged race car was the first rear-engined car to compete in the Indianapolis 500 and was owned by Preston Tucker to promote his ground-breaking car.

Ed Trainor Special at the 1951 Indianapolis qualification trials

A Legacy Tested

One hundred shares of Lincoln Automobile Company stock were issued just months prior to the stock market crash of 1929. Litigation brought by industrialist Henry Ford challenged the naming rights of EVT's dealership, following Ford's purchase of Lincoln Motor Company from renowned engineer Henry Leland in 1922.

Lincoln Automobile Company stock certificates, 1929

A Name Reinvented

EVT's original Motor Row showroom was renamed Trainor Motors and relocated to Hyde Park — carrying the family's passion for exceptional motorcars into a new chapter. A legacy that endures to this day through Chicago Vintage Charters.

Trainor Motors, Hyde Park
"From my earliest years, I have had an insatiable fascination with cars, the remarkable history of motorcars and the joy and excitement they bring to persons of all ages."
— John McNabola, Restoration Specialist & Geneva Concours d'Élégance Judge

Inquiries

Reserve
Your Motorcar

We look forward to making your occasion unforgettable. Reach out directly or use the reservation inquiry form.

Telephone847 845-1494
Service AreaGreater Chicagoland & the Midwest
John McNabola with a classic car

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