Chicago Car Service | Car Service Chicago IL
Detailed Drivers is Chicago's premier car service, providing flat-rate transportation across the Loop, Magnificent Mile, North Shore suburbs, and both airports. Sedan from $100/hr. O'Hare from $100. No surge pricing — not during Friday rush on the Kennedy, not during convention week, not on Bears game day.
Chicago car service rates and pricing
Flat rates locked at booking. No surge during rush hour, conventions, game days, or weather events.
| Vehicle | Hourly rate | O'Hare (ORD) | Midway (MDW) | Min hours |
|---|---|---|---|---|
| Mercedes-Benz S-Class Sedan | $100/hr | from $100 | from $100 | 2 hr |
| Cadillac Escalade ESV SUV | $115/hr | from $100 | from $100 | 2 hr |
| Mercedes-Benz Sprinter Van | $150/hr | from $135 | from $110 | 3 hr |
Rates include vehicle, chauffeur, fuel, tolls on I-90/I-94 Skyway, and meet-and-greet. Gratuity not included. Prices effective March 2026.
Chicago car service vs Uber and Lyft
Uber Black and Lyft Lux use surge pricing. Detailed Drivers does not — your rate is locked at booking.
| Feature | Detailed Drivers | Uber Black | Lyft Lux |
|---|---|---|---|
| O'Hare to Loop | from $100 | $65-$195 | $60-$180 |
| Surge risk | None | 2.5-4.0x peak | 2.0-3.5x peak |
| Flight tracking | Included | None | None |
| Meet-and-greet | Included | No | No |
| Driver vetting | Licensed, background checked, drug tested | Self-reported | Self-reported |
| Corporate billing | Centralized invoicing | Personal card only | Personal card only |
| Vehicle condition | Inspected fleet | Owner's personal car | Owner's personal car |
Friday rush hour (4-7 PM on the Kennedy)
Uber Black O'Hare to Loop: $65 base x 3.0x surge = $195
Detailed Drivers flat rate: from $100
You save $120 (62%)
McCormick Place convention week + snow
Uber Black O'Hare to Loop: $65 base x 4.0x surge = $260
Detailed Drivers flat rate: from $100
You save $185 (71%)
Chicago airport transfers
O'Hare International Airport (ORD) handled 83.3 million passengers in 2024 (Chicago Department of Aviation). Midway Airport (MDW) served 23.6 million. Detailed Drivers provides flat-rate transfers from both airports to every Chicagoland destination.
O'Hare International Airport (ORD)
17 miles from the Loop via I-90/94 Kennedy Expressway. 30 min off-peak, 45-75 min rush hour. 4 terminals + International Terminal 5.
Midway International Airport (MDW)
11 miles from the Loop via I-55 Stevenson Expressway. 20 min off-peak, 30-50 min rush hour. Single terminal.
All airport transfers include flight tracking, meet-and-greet at the terminal exit, luggage assistance, and complimentary wait time (60 min international, 30 min domestic). Your chauffeur monitors your inbound flight and adjusts arrival time if you land early or late.
Chicago fleet — vehicles and capacity
Every vehicle is commercially registered, inspected quarterly, and maintained to executive standards. No personal cars.
Mercedes-Benz S-Class Sedan
3 passengers, 2 bags
$100/hr | O'Hare from $100
Executive airport runs, solo or couple travel
Cadillac Escalade ESV SUV
6 passengers, 6 bags
$115/hr | O'Hare from $100
Groups, families, luggage-heavy trips
Mercedes-Benz Sprinter Van
10-14 passengers
$150/hr | O'Hare from $135
Convention groups, corporate teams, wedding parties
Chicago car service options
Detailed Drivers provides airport transfers, hourly hire, corporate travel, and event transportation across Chicagoland.
Airport transfers
Flat-rate O'Hare and Midway transfers with flight tracking and meet-and-greet at all terminals.
Learn moreChauffeur service
Professional chauffeur hire for multi-stop business days, shopping, dining, and city tours.
Learn moreBlack car service
Executive black car for corporate travel, client entertainment, and premium transportation.
Learn moreLimousine service
Stretch and SUV limousines for weddings, proms, galas, and special occasions.
Learn moreSprinter van rental
Mercedes Sprinter vans for convention groups, corporate outings, and wedding parties up to 14.
Learn moreCorporate travel
Centralized billing, priority booking, and dedicated account management for Chicago businesses.
Learn moreCity-to-city
Chicago to Milwaukee (92 mi), Indianapolis (184 mi), Detroit (283 mi), and St. Louis (297 mi).
Learn moreHourly hire
As-directed service from $100/hr with unlimited stops and flexible scheduling.
Learn moreExecutive car service
C-suite transportation with NDA-ready chauffeurs and discreet, premium vehicles.
Learn moreCorporate car service in Chicago
Chicago is home to 36 Fortune 500 headquarters — more than any U.S. city except New York. Detailed Drivers provides executive ground transportation for companies in the Loop financial district, along the Magnificent Mile, and across the western suburbs.
Loop and financial district
Boeing global headquarters on Wacker Drive, CME Group on South Wacker, BMO Financial Group, Northern Trust, and the Chicago Board of Trade at LaSalle and Jackson. Detailed Drivers provides daily executive transportation for traders, portfolio managers, and C-suite executives across LaSalle Street.
Suburban headquarters
Abbott Laboratories in Abbott Park, Baxter International in Deerfield, Walgreens Boots Alliance in Deerfield, Caterpillar in Irving (Texas HQ relocated, but large Chicago presence), McDonald's West Loop HQ, and Kraft Heinz on Wacker Drive. Airport-to-suburban-campus transfers are our most-booked corporate route.
Corporate account features
McCormick Place, sports, and events
McCormick Place is North America's largest convention center at 2.6 million square feet of exhibit space, hosting over 200 events per year. Detailed Drivers provides convention transportation from O'Hare and Midway to McCormick Place and Loop hotels.
Convention and trade show transportation
Major McCormick Place events include the Chicago Auto Show (1 million+ attendees), NRA Show, PACK EXPO, IMTS (International Manufacturing Technology Show), and RSNA (radiology). Detailed Drivers coordinates multi-vehicle airport pickups, hotel shuttles, and door-to-door executive transfers for convention attendees and exhibitors.
O'Hare to McCormick Place: $100 sedan (22 miles via I-90/94 to Lake Shore Drive, 35-60 min depending on traffic). Midway to McCormick Place: $100 sedan (8 miles via I-55, 15-25 min).
Chicago sports venues
Soldier Field — Chicago Bears (NFL), 61,500 seats. Museum Campus Drive off Lake Shore Drive. Game-day VIP drop-off at Gate 0.
United Center — Chicago Bulls (NBA) and Blackhawks (NHL), 23,500 seats. 1901 W Madison St, West Loop.
Wrigley Field — Chicago Cubs (MLB), 41,649 seats. 1060 W Addison St, Lakeview. Skip the parking nightmare on Clark Street.
Guaranteed Rate Field — Chicago White Sox (MLB), 40,615 seats. 333 W 35th St, Bridgeport.
Areas we serve in Chicago
Detailed Drivers covers all of Chicagoland — downtown neighborhoods, North Shore, western suburbs, and south suburbs.
How to book Chicago car service
Book online in 2 minutes or call for immediate assistance.
Request a quote
Visit detaileddrivers.com/reservations or call (888) 420-0177. Enter your pickup and drop-off locations with date and time.
Select your vehicle
Choose from Mercedes-Benz S-Class sedan ($100/hr), Cadillac Escalade ESV ($115/hr), or Mercedes-Benz Sprinter Van ($150/hr).
Confirm booking
Receive instant confirmation with flat-rate pricing. No surge, no hidden fees. Your rate is locked.
Meet your chauffeur
Your chauffeur contacts you 24 hours before pickup. Airport pickups include flight tracking and meet-and-greet at the terminal.
Or call (888) 420-0177 — available 24/7
Car service near Chicago
Detailed Drivers also serves these nearby cities with the same flat-rate pricing and professional chauffeurs.
Chicago car service FAQ
Common questions about booking car service in Chicago.
Detailed Drivers is Chicago's premier car service, providing flat-rate executive transportation across Chicagoland 24/7. As of 2026, Detailed Drivers serves 67+ cities across the United States with a fleet of Mercedes-Benz S-Class sedans, Cadillac Escalade ESV SUVs, and Mercedes-Benz Sprinter Vans. Chicago car service starts at $100/hr for a sedan with O'Hare International Airport (ORD) transfers from $100 and Midway Airport (MDW) transfers from $100. All pricing is locked at booking-rate with no surge during rush hour on the Kennedy Expressway, McCormick Place convention weeks, Bears game days at Soldier Field, or winter weather events. Corporate accounts are available with centralized billing for Loop financial district firms, Fortune 500 headquarters, and law practices.
Last Updated: April 2026
