Rent a Bentley in Chicago
Compare 4 companies offering Bentley rentals in Chicago. Browse ratings, reviews, and contact info.
4 Companies with Bentley in Chicago
Next LVL Exotics
Chicago, Illinois
Luxury Rentals USA
Chicago, Illinois
CelebLux Limos
Chicago, Illinois
Luxury Car Rental Chicago | Exotic Cars IL
Chicago, Illinois
Bentley Rentals in Other Cities
Market Snapshot
Bentley Rental Market in Chicago
Pricing, availability, and what to know before you book
Our directory tracks 4 operators offering Bentley rentals in Chicago. The market is mid-sized: enough operators to compare rates, but not so many that last-minute bookings are reliably available for peak weekends.
Bentayga and Flying Spur are the most commonly listed Bentley models across Chicago fleets. Availability skews toward the models operators find easiest to source locally — if you need a specific variant not listed here, contact operators directly as fleet rotation happens throughout the year.
Across United States, Bentley rental rates typically run $1,200–$2,500 per day. Chicago pricing tends to track national norms, though rates shift with demand: high-profile events, holidays, and local sports seasons can push prices to the top of that range or beyond. The lowest rates are generally available Tuesday through Thursday outside of peak season.
Chicago sits within a United States market where Bentley rentals serve a mix of corporate, leisure, and event clients. Use the operator listings above to compare pricing, availability, and verified reviews before booking.
Rental Guide
Renting a Bentley in Chicago
Renting a Bentley in Chicago
Chicago's Bentley rental market is modest in scale but serves the city's strong luxury event and corporate demand. Companies operate in the Gold Coast and River North. Rates: $650–$900/day for a Continental GT, $1,000–$1,500/day for a Flying Spur W12.
Models & Pricing
The Continental GT and Flying Spur are available through Chicago specialty companies. The Bentayga is available at some companies and practical for North Shore drives. Deposits: $4,000–$7,000. Mileage: 150–200 miles/day. The market is almost entirely seasonal — April through October.
Where to Drive
Lake Shore Drive south from Foster Beach to the Museum Campus is Chicago's signature boulevard — 10 miles of lakeshore driving with the skyline as a constant presence. The Continental GT's grand proportions suit the broad, well-maintained asphalt. Sheridan Road north along the North Shore through Evanston, Wilmette, and Winnetka runs alongside Lake Michigan through wealthy residential bluffs — unhurried, architecturally impressive. Green Bay Road through Lake Forest and Lake Bluff continues the North Shore to the Wisconsin border for those wanting a longer rural run. Michigan Avenue (Magnificent Mile) between Oak Street and the Chicago River is the prestige street circuit — more about being seen than driving.
Practical Tips
Chicago potholes are a genuine concern, particularly after winter. Inspect tyre sidewalls on collection. Valet at the Four Seasons, Waldorf Astoria, and Langham are all experienced with Bentley-class vehicles. Winter rentals (November–March) are not advisable in a rear-wheel-drive Continental GT — the Bentayga's AWD handles Chicago winters better. 91-octane premium available throughout the metro.
FAQ
Can I rent a Bentley for a Chicago gala or event? Yes — most specialty companies accommodate event rentals with flexible hours. Book 2–3 weeks ahead for summer weekend events.
Is Lake Shore Drive good for a Bentley drive? On a Sunday morning at 7am it's genuinely enjoyable. On a weekday afternoon it's stop-and-go — the experience is purely visual at that point.