Chicago Lakefront Scenic Drive

A full-size executive sedan that seats 3 passengers with room for 3 full bags in the trunk, the Lincoln Continental is our workhorse for solo and pair travel around Chicago. Riders get heated and cooled rear leather seats, a quiet cabin that holds up on the Kennedy at rush hour, and rear climate controls they can set themselves. It is the car most O'Hare and Midway regulars book for early-morning pickups: the chauffeur tracks the flight, meets arrivals at baggage claim, and handles bags. Corporate accounts use it for downtown client runs and roadshow legs between the Loop and the suburbs, and couples book it for anniversary dinners and theater nights. Two-hour minimum, flat $130 to O'Hare.

Chicago's most requested SUV. The Escalade ESV combines commanding presence with luxurious comfort — perfect for corporate groups, wedding parties, and VIP airport transfers.

Hand-built in Goodwood, England — 6.75L twin-turbo V12, 563 hp, rear-hinged coach doors, and a fiber-optic Starlight Headliner with 1,340 hand-set points of light. Seats 3 in lambswool-rugged rear executive seating with a chilled champagne cooler between the rear quarters. Used for Drake / Peninsula / Four Seasons wedding exits, downtown proposals, and red-carpet arrivals at the Lyric Opera or the Auditorium Theatre. $500/hr, 3-hour minimum, white-glove chauffeur in formal attire.

The Bentley Flying Spur is a hand-built British sedan that seats 3 to 4 with 2 to 3 bags, and it splits the difference between a chauffeured limousine and a driver's car, with a twin-turbo W12 under the hood and a hand-stitched cabin in back. Rear passengers get diamond-quilted leather, massaging seats, the Naim audio system, mood lighting, rear touchscreens, and chilled champagne flutes. Couples book it as a wedding getaway car when they want something more exclusive than a stretch, and it photographs beautifully outside Gold Coast and downtown venues. It also serves as a discreet VIP sedan for visiting executives and high-profile arrivals who recognize the badge and want privacy rather than a parade. Three-hour minimum, $495 flat to O'Hare.