Chicago Car Service
& Executive Transportation
Experience premier luxury car service in Chicago with professional chauffeurs, O'Hare and Midway airport transfers, and executive transportation for the Windy City's most discerning travelers.
BACKED BY WORLD CLASS BRANDS
Preferred choice for assistants, planners, and travel managers who need it done right.
The
Windy City's
Finest
Chicago stands as one of America's great business hubs—and getting around this magnificent city demands transportation that matches its stature.
As the gateway to American commerce, Chicago's O'Hare International Airport ranks among the world's busiest airports, welcoming over 80 million passengers annually. Whether you're arriving for meetings at the Chicago Board of Trade, attending conventions at McCormick Place, or visiting clients along the Magnificent Mile, your ground transportation sets the tone for every engagement.
Detailed Drivers provides premier chauffeur service throughout Chicagoland, combining Midwestern hospitality with luxury service standards. Our professional chauffeurs navigate the city's iconic grid system, Lake Shore Drive traffic, and complex expressway interchanges with the expertise that only local knowledge provides.
From seamless airport transfers to hourly charters for corporate roadshows, our Chicago black car service delivers consistent excellence whether you're headed to the Loop financial district, Lincoln Park dining, or the North Shore suburbs.
Areas Served
Downtown Chicago, O'Hare & Midway, North Shore & Suburbs
Chicago Transportation Solutions
From O'Hare airport arrivals to McCormick Place conventions, discover comprehensive luxury transportation tailored to Chicago's unique demands.
O'Hare & Midway Airport Transfers
Seamless Chicago airport transfers with real-time flight tracking and meet-and-greet service. Our chauffeurs know every terminal at O'Hare International and Midway, ensuring stress-free arrivals and departures from one of the world's busiest airport hubs.
- Real-time flight tracking
- All O'Hare terminals covered
- Midway Airport service
- Complimentary wait time
Corporate & Financial District Travel
Executive transportation for Chicago's bustling business community. From the Chicago Board of Trade to LaSalle Street financial firms, we understand the demands of corporate travel in the Windy City with dedicated account management and monthly billing.
- Loop & financial district expertise
- Corporate account billing
- Roadshow logistics
- Client entertainment
McCormick Place Convention Service
Specialized transportation for North America's largest convention center. Whether you're attending a trade show, hosting delegates, or coordinating group logistics, our team delivers flawless convention transportation with Sprinter vans and executive sedans.
- Convention center specialists
- Group transportation
- Multi-day event support
- Executive shuttle service
Chicago Sports & Entertainment
Luxury transportation to every major Chicago venue. From Bears games at Soldier Field to Bulls and Blackhawks at United Center, Cubs at Wrigley, and Sox at Guaranteed Rate Field—arrive in style and avoid parking hassles.
- Soldier Field & United Center
- Wrigley Field service
- VIP venue access
- Game-day traffic navigation
Magnificent Mile & Gold Coast
Premium chauffeur service for Chicago's most prestigious neighborhoods. From Michigan Avenue shopping excursions to Gold Coast dining, our drivers provide discreet, sophisticated transportation for the city's most discerning clientele.
- Shopping & dining transport
- Gold Coast specialists
- River North nightlife
- VIP concierge service
North Shore & Suburban Service
Comprehensive coverage extending throughout Chicagoland. From Evanston and the North Shore estates to Naperville, Oak Brook, and Schaumburg, we connect Chicago's suburbs to airports, downtown, and destinations throughout the region.
- North Shore coverage
- Naperville & western suburbs
- Suburban airport transfers
- City-to-suburb connections
Hourly Charter Service
Flexible as-directed service for business meetings, city tours, or multi-stop itineraries. Your dedicated chauffeur and vehicle remain at your disposal throughout your reserved hours, perfect for executives with packed Chicago schedules.
- Unlimited stops
- Flexible scheduling
- Full-day availability
- Business meeting transport
Sprinter Van Group Transportation
Executive group travel in our Mercedes Sprinter fleet. Ideal for corporate teams, wedding parties, convention groups, and family gatherings requiring comfortable, stylish transportation for up to 14 passengers throughout Chicago.
- Up to 14 passengers
- Corporate group travel
- Airport group transfers
- Event shuttle service
Chicago Neighborhoods & Areas We Serve
Comprehensive luxury car service coverage throughout Chicago's diverse neighborhoods, from the iconic downtown core to the distinguished suburbs.
The Loop
Financial district & downtown core
Magnificent Mile
Michigan Avenue shopping & hotels
River North
Dining, galleries & nightlife
Gold Coast
Upscale residential & lakefront
Lincoln Park
Parks, dining & entertainment
Wicker Park
Trendy boutiques & restaurants
Oak Park
Historic suburb & Frank Lloyd Wright
Evanston
Northwestern University & North Shore
Naperville
Western suburb business district
Schaumburg
Corporate campuses & convention hotels
Plus comprehensive coverage throughout Will, DuPage, Lake, and Cook counties
Book Chicago ServiceOur Chicago Luxury Fleet
From executive sedans for Loop meetings to Sprinter vans for McCormick Place groups, our meticulously maintained fleet serves every Chicago transportation need.
First Class
Mercedes S-Class
SUV
Cadillac Escalade
Van
Mercedes Sprinter
Black SUV
Lincoln Navigator
Executive
BMW 7 Series
Business
Cadillac XT6
The Chicago Chauffeur Experience
Midwestern hospitality meets world-class luxury service. Our professional chauffeur service delivers an exceptional travel experience that reflects Chicago's legacy as a hub of commerce, culture, and sophistication.
O'Hare & Midway Expertise
As one of the world's busiest airport hubs, O'Hare demands expert navigation. Our chauffeurs know every terminal, every pickup point, and the optimal routes to get you downtown efficiently whether you're arriving or departing.
Loop & Financial District
From the Chicago Board of Trade to LaSalle Street's financial towers, our drivers understand executive transportation in the city's business core. We navigate construction, game-day diversions, and rush-hour patterns seamlessly.
Midwestern Hospitality
Chicago is known for warm, genuine hospitality—and our service reflects that tradition. Expect professional courtesy, local recommendations, and the kind of personalized attention that makes every ride memorable.
Included in Every Chicago Ride
- Bottled water & refreshments
- Complimentary WiFi
- Phone chargers (all types)
- Flight tracking & monitoring
- Climate-controlled interior
- Real-time trip updates
- Door-to-door service
- Luggage assistance
- Professional chauffeur
- 24/7 Chicago dispatch
- Meet-and-greet options
- Flexible scheduling
Ready to experience Chicago's finest car service?
Book Your RideWhy Chicago Chooses Detailed Drivers
From Fortune 500 executives to visiting dignitaries, discerning travelers trust our luxury chauffeur service for their Chicago ground transportation needs.
Chicago Licensed & Insured
Fully licensed for Chicago and Illinois commercial transportation. All vehicles carry comprehensive insurance, and every chauffeur meets city and state requirements for professional ground transportation.
Professional Chicago Chauffeurs
Our drivers know Chicago intimately—from navigating Loop traffic patterns to finding the best routes during Cubs games. Each chauffeur undergoes rigorous background checks and training in executive protocol.
On-Time Guarantee
We understand Chicago time. From O'Hare's complex terminals to McCormick Place's multiple buildings, our chauffeurs arrive 15 minutes early and navigate the city's famously unpredictable traffic with expertise.
5-Star Chicago Service
Midwestern hospitality meets luxury service. Our Chicago clients consistently rate us 5 stars for our combination of warm, professional service and uncompromising attention to detail.
Global Network Access
Need car service beyond Chicago? Your Detailed Drivers account provides access to our worldwide network in 200+ cities, maintaining the same standards whether you're in the Loop or London.
Transparent Chicago Pricing
No surge pricing during conventions or game days. Our all-inclusive quotes include tolls, parking, and gratuity guidelines. What you see is what you pay—every trip, every time.
What Chicago Clients Say
Our reputation in Chicago is built on consistently exceeding expectations for executives, event planners, and discerning travelers throughout Chicagoland.
"We've used Detailed Drivers for three years of quarterly board meetings and investor roadshows. Their drivers know the Loop like the back of their hand, and the consistency is remarkable. Whether we're picking up clients at O'Hare or shuttling between the Board of Trade and our offices, they never miss."
Michael D.
Managing Director, LaSalle Street Firm
"Coordinating transportation for major conventions is complex. Detailed Drivers handles our VIP delegates, speaker shuttles, and executive airport transfers with military precision. Their Sprinter vans are always immaculate, and their communication during multi-day events is exceptional."
Patricia W.
Event Director, McCormick Place
"Living in Winnetka and commuting to the Loop, I've tried every service. Detailed Drivers stands apart—the cars are spotless, the chauffeurs are professional, and they understand that my time matters. They've become an extension of how I do business in Chicago."
James K.
North Shore Executive
Book Your Chicago Car Service
Reserving luxury transportation in Chicago is simple. Here's how to book your premium chauffeur service in just a few steps.
Select Your Service
Choose from O'Hare/Midway airport transfers, hourly charter, point-to-point, or McCormick Place convention service.
Choose Your Vehicle
Select from executive sedans for Loop meetings, SUVs for North Shore trips, or Sprinter vans for group transportation.
Confirm Your Details
Enter your Chicago pickup location, destination, date, time, and any special requirements for your trip.
Enjoy Your Ride
Your professional Chicago chauffeur arrives 15 minutes early. Relax and experience the finest ground transportation in the Windy City.
Chicago Car Service FAQs
Everything you need to know about luxury transportation in Chicago
Explore Our Services
Discover more ways Detailed Drivers can serve your Chicago transportation needs.
Airport Transfers
O'Hare & Midway service with flight tracking
Corporate Travel
Executive transportation for Chicago businesses
Black Car Service
Premium sedan service throughout Chicagoland
Hourly Hire
Flexible charter service for meetings & events
Sprinter Van Rental
Group transportation for conventions & events
Chauffeur Service
Professional drivers for every occasion
Limousine Service
Special occasions & celebrations
Our Fleet
View our luxury Chicago vehicles