Travel in a Rolls-Royce with private chauffeur service
1–8 hrs
Private chauffeur, luxury vehicle
Travel through Chicago in a Rolls-Royce Cullinan or Black Badge Edition with a private chauffeur. This service is offered in partnership with Trump International Hotel Chicago.
You may be eligible for a refund if you cancel within 24 hours of booking your reservation. No refunds are provided after 24 hours of reservation confirmation.
Product ID: 2PJS7W
Rescheduling is available up to 24 hours before your reservation. Changes after that point incur a rescheduling fee.
DS Luxury, 1339 S Wood St, Chicago, IL 60608
10/10 experience as someone who honestly does not know much about cars. There were 3 of us who got to experience being chauffeured in an absolutely stunning Maybach. Not only were we comfortable, got to ride in style, we also had Jose to show us around to give us an amazing experience!! He allowed us to curate our own playlist, provided us information about places/sites around downtown, and even allowed us to take pictures with other cars once completing our trip.
Jaden Young
August 17, 2026
10/10 experience as someone who honestly does not know much about cars. There were 3 of us who got to experience being chauffeured in an absolutely stunning Maybach. Not only were we comfortable, got to ride in style, we also had Jose to show us around to give us an amazing experience!! He allowed us to curate our own playlist, provided us information about places/sites around downtown, and even allowed us to take pictures with other cars once completing our trip.
Jaden Young
August 17, 2026
Cruise Chicago’s lakefront in an exotic vehicle with skyline and landmark views
Cruise Chicago on a 10-mile Lamborghini Urus ride
See Chicago landmarks from the back seat of a Rolls-Royce with a private driver
Twin-turbo V8 performance with grand-touring comfort
Experience supercar power with SUV versatility in Chicago
Open-air hybrid performance in a McLaren Artura Spider