Date night
A Wraith at the door at seven. Lake Shore Drive as the sky turns, a table in River North, and the skyline from somewhere high before the long way home.
Occasions
Wedding & date night car rentals in Chicago
Weddings, anniversaries, proposals, quiet dinners and important arrivals.
Proposals
The lakefront at the last of the light, the city across the water, a car waiting a few steps away. The Adler overlook and the quiet paths of Northerly Island were made for the question.
Anniversaries
Mark the year with something unhurried: dinner, a drive, a view. With a chauffeur, neither of you has to think about the road.
Weddings
The Cullinan, the Ghost and the Wraith, alone or together in a package for the whole party. Portraits at the Riverwalk, Buckingham Fountain or the Cultural Center.
Birthdays & celebrations
A Huracán EVO Spyder for the milestone, or a Maybach for an evening with friends. Some birthdays should be impossible to forget.
Corporate & VIP
Client dinners on the Gold Coast, meetings in the Loop, a guest collected from O’Hare or Midway in a Maybach GLS 600 or an S580, with a professional chauffeur.
Photo shoots, reels & content days
Sometimes the photograph is the point: a portrait, a reel, a music video, a campaign. Share the place and the hour and the car will be ready for the light. See the photo spots guide or ask about creator collaborations.
Drives
Chicago, slowly
Lake Shore Drive, end to end
The classic. Hollywood Avenue to the Museum Campus with Lake Michigan on one side and the skyline on the other. Best at sunrise or after 8 pm when traffic thins.
Wacker Drive & the river bridges
Lower and Upper Wacker trace the Chicago River past Marina City, the Wrigley Building and the Merchandise Mart. Lights on the water make night drives unforgettable.
The Magnificent Mile
A slow cruise down Michigan Avenue from Oak Street Beach past the Water Tower and the Tribune Tower to the river. Best taken slowly.
Museum Campus & Adler overlook
Park with the full skyline across the harbor. The single best photo backdrop in the city.
Gold Coast & Astor Street
Historic mansions and tree-lined streets, then dinner on Rush and Oak.
Sheridan Road to the North Shore
Lakefront curves through Evanston, Wilmette and Winnetka. A favorite convertible afternoon.
Southwest suburbs evening loop
From Orland Park out along the Palos forest preserves and La Grange Road — easy access, quieter roads, beautiful in autumn.
Where to arrive
Places worth an entrance
- The Langham, The Peninsula and the Waldorf Astoria for hotel arrivals
- Rooftop lounges in River North and the West Loop
- Steakhouses and supper clubs on Rush Street and in River North
- Fulton Market restaurant row
- Chicago Cultural Center, Ivy Room and Riverwalk venues for weddings
- Navy Pier and the Museum Campus for lakefront photos
Venue names are ideas for planning, not partnerships. Always follow venue valet and parking rules.
Reserve
Plan the occasion
Tell us the car, the date and where the day begins. Every booking is confirmed personally.