Corporate Travel
Chicago
Elevate your executive transportation with Chicago's premier corporate car service. From Loop board meetings to O'Hare arrivals, we deliver the punctuality, discretion, and professionalism that Fortune 500 companies headquartered in the Windy City demand.
Executive Ground Transportation for the Midwest Business Capital
Chicago stands as the commercial heart of the Midwest, home to more Fortune 500 headquarters than any city outside New York. With Boeing, United Airlines, Abbott Laboratories, Caterpillar, Walgreens Boots Alliance, and McDonald's calling Chicago home, the demand for reliable executive transportation is constant. Detailed Drivers has built its reputation serving the C-suites and corporate travelers who drive the region's economy.
Our corporate travel services extend far beyond simple point-to-point transportation. We understand that when a CFO needs to reach meetings at three Loop law firms, a lunch on the Magnificent Mile, and a 5 PM flight from O'Hare, every minute counts. Our coordination team manages complex itineraries with precision, adjusting routes based on Chicago traffic patterns and CTA disruptions.
For executive assistants managing travel for multiple executives, our corporate account platform simplifies booking, tracking, and expense reconciliation. Custom billing codes enable department-level cost allocation, while our API integrations sync with Concur, SAP Concur, and major corporate travel management systems.
Whether you're coordinating board arrivals at O'Hare, managing daily executive commutes from the North Shore, or planning transportation for a McCormick Place trade show, Detailed Drivers delivers the consistency and professionalism your organization requires.
Serving Every Chicago Business District
From the Loop's canyons to suburban campuses, we know Chicago's corporate geography.
The Loop
LaSalle Street financial district and corporate headquarters
Magnificent Mile
Michigan Avenue hotels and executive offices
River North
Creative agencies, tech companies, and hospitality
West Loop / Fulton Market
Google Chicago, corporate innovation centers
Suburban Corridors
Schaumburg, Deerfield, Lake Forest headquarters
McCormick Place
Convention center and Soldier Field events
Corporate Account Features
Purpose-built for enterprise travel management, our platform streamlines every aspect of executive transportation.
Monthly Billing & NET-30 Terms
Streamlined invoicing with detailed trip breakdowns by cost center, department, or project. Compatible with Concur, SAP, and all major expense systems.
Chicago-Based Account Management
Your account manager knows Chicago—from navigating the Loop during rush hour to understanding suburban corporate campus logistics.
Roadshow & Convention Support
Expert coordination for investor roadshows, trade shows at McCormick Place, and multi-stop executive itineraries across Chicagoland.
Confidentiality Protocols
NDA-bound chauffeurs, encrypted booking systems, and discretion protocols trusted by law firms, financial institutions, and Fortune 500 executives.
Custom Reporting
Detailed analytics on travel spend, usage patterns, and carbon footprint. Monthly reports delivered to travel managers and finance teams.
Global Network
One account for ground transportation worldwide. We coordinate with trusted partners in 500+ cities for seamless executive travel beyond Chicago.
McCormick Place & Trade Show Specialists
Chicago hosts more trade shows than any other U.S. city. Our team has coordinated executive transportation for major conventions at McCormick Place, Navy Pier, and downtown conference hotels. We understand the logistics of high-volume arrivals and the importance of impeccable timing.
- Dedicated coordinator for multi-day conventions
- VIP shuttle services between hotels and venues
- O'Hare arrival coordination for out-of-town executives
- After-hours service for client dinners and events
Chicago Corporate Metrics
Trusted by Chicago's Business Leaders
From LaSalle Street to the Mag Mile, corporate clients rely on our executive car service.
"Detailed Drivers has been our exclusive ground transportation partner for three years. Their reliability is exceptional—never a missed pickup, even during Chicago's worst weather. The monthly billing integrates perfectly with our expense system, and their drivers know every shortcut in the Loop."
Thomas Brennan
Chief Operating Officer
Fortune 100 Industrial Company
"Our partners demand perfection, and Detailed Drivers delivers. From O'Hare pickups to courthouse arrivals, they understand the time-sensitive nature of legal work. Their confidentiality is absolute—essential for our high-profile clients."
Michelle Rodriguez
Executive Assistant to Managing Partner
LaSalle Street Law Firm
"We consolidated Chicago ground transportation to Detailed Drivers last year. The result: 28% cost savings, zero complaints from partners, and a corporate portal that makes booking and reporting effortless. Their McCormick Place coordination during our annual conference was flawless."
David Kim
Director of Corporate Travel
Global Consulting Firm
Complete Chicago Executive Transportation
Explore our full range of services for corporate travelers in Chicago.
Airport Transfers
O'Hare & Midway service
Black Car Service
Executive sedans & SUVs
Chauffeur Service
Professional drivers on demand
Sprinter Van
Group executive transport
Hourly Charter
Flexible as-directed service
City-to-City
Chicago to Milwaukee, Indy & more
Our Fleet
View luxury vehicles
EA Program
Executive assistant tools
