In Chicago, how you arrive is who you are. A professional chauffeur, a spotless black fleet, on time and flat-rate — the city is yours.
SCAN TO BOOKdrivingmogul.com
From a 5 a.m. flight to the biggest night of your life — booked ahead so you never wait.
Flight-tracked pickups & drop-offs at O'Hare & Midway. Curbside when you land — no waiting, no surge.
Make the entrance the day deserves. Immaculate vehicle, on-schedule, chauffeur in black tie.
Dinner, the game, a night downtown. Door to door across Chicago — no parking, no rideshare roulette.
Reliable, discreet travel for meetings, clients, and roadshows. Billed simply, on time every time.
Graduations, anniversaries, birthdays. Safe, professional, and unforgettable.
Keep the car for the evening. Multiple stops, one driver, zero hassle.
Meticulously maintained for your comfort and safety — professionally detailed before every ride.
Full-size luxury SUV · our flagship
Bold, spacious, first-class ride
The executive standard
Sleek, sharp, understated luxury
Additional vehicles available on request · Larger groups & special requests — just ask.
You enjoy the moments. We'll handle the ride.
Booked in advance. Priced up front. Driven by someone whose name you'll know.
We plan around your schedule and Chicago traffic — you're never left waiting.
Know your fare before you ride. No surge, no meter anxiety, no surprises.
Fully licensed, fully insured, professionally maintained. Your safety first.
The same professional, in a suit, who treats your ride like it's the only one that day.
Flat-rate quotes — no surge, no meter. Final price confirmed when you book.
Tell us the details and we'll confirm by text or call. Prefer to talk? Call any time — we answer, 24/7.
📞 (708) 554-4028
Under a minute. We'll follow up to confirm.
Driving Mogul serves all of Chicago and the greater metro — downtown and the Loop, O'Hare (ORD) and Midway (MDW) airports, and suburbs including Naperville, Oak Brook, Evanston, and Schaumburg. Farther trips are available on request.
Yes. We provide flight-tracked airport transfers to and from both O'Hare and Midway. Your chauffeur monitors your flight and is curbside when you land — flat-rate, no surge, no waiting.
Pricing is flat-rate and quoted up front before your ride, so there's no surge and no surprises. Rates depend on distance, vehicle, and occasion — call or text (708) 554-4028, or request a quote online, for an exact price in under a minute.
Yes — you can book Driving Mogul by the hour (as-directed) for events, multiple stops, weddings, or a night out. One professional chauffeur stays with you the entire time.
We recommend booking ahead to guarantee availability, especially for airport runs, weddings, and busy nights — but we operate 24/7, so call or text (708) 554-4028 anytime and we'll do our best to accommodate same-day requests.
Our signature vehicle is the black Lincoln Navigator, alongside a luxury fleet including the Cadillac Escalade, Mercedes-Benz S-Class, and Cadillac CT5 — all immaculately maintained and professionally chauffeured.
O'Hare & Midway · Downtown & the Loop · Greater Chicago metro · Suburbs on request
Available around the clock. Book ahead for guaranteed availability.