Chicago Sightseeing Tours

Experience the best of the city on your own terms with a private, custom city tour. We guarantee a 10-minute early arrival for every initial pickup to ensure a stress-free start.
Call +1 (708) 968-4226 to secure your professional city chauffeur.

Request a Custom Quote
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10-Minute Early Guarantee

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Custom Itineraries

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Expert Local Navigation

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No Parking Hassles

Custom Itineraries and Local Landmarks

When you book a sightseeing tour with us, you are completely in control of the schedule. You choose the local landmarks you want to see, from the heights of the Willis Tower to the beautiful grounds of Millennium Park. Your private chauffeur handles all the navigation and heavy city traffic while you relax and take in the views. We also offer expertly guided Spanish-language tours of Chicago to ensure all of our clients can explore the city comfortably.

Stress-Free City Exploration

  • Skip the uncertainty of public transit or the wait times of rideshare apps. We provide a seamless experience where your chauffeur stays on standby, allowing you to spend as much time as you like at Navy Pier or the Museum Campus. We deliver a standard of excellence that ensures your tour is smooth, private, and perfectly timed.
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A man and woman sit in the back of a luxury car, smiling as they look out the window at the iconic Chicago Theatre sign.

Our Touring Fleet

 We maintain a meticulously detailed fleet to accommodate any traveler's needs

Passengers: Up to 6

Luggage: 5-6 Bags


Ideal For: Families, Golf Trips, and Executives.

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  • Interior of a luxury van with blue LED lighting, starry ceiling, seats, and a cityscape view.

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  • Inside of a black luxury van with leather seating, a large screen, and city views.

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Passengers: 14

Luggage: 15 Bags


Ideal For: Business Groups, Airport Runs, Shuttles and Wedding Parties.

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  • Interior of a trolley car with wooden panels and long benches. Sunlight streams through large windows.

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  • Inside of a wooden trolley with city views at dusk. Interior has long benches, purple lights, and circular windows.

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  • Interior of a trolley car with wooden panels, purple lighting, and city skyline views through the windows.

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Passengers: 24

Luggage: N/A


Ideal For: Shuttles, Brew Tours, Wine Tours, Wedding Parties, and Holiday Tours.

Straightforward Billing

We believe in straightforward billing with no hidden surprises. Please note our operational pricing guidelines:

  • Taxes: A flat $4.50 tax is applied to all trips.
  • Gratuity: A customary 20% gratuity is automatically applied to all orders to compensate your professional chauffeur.
  • Family Travel: Car seats (rear-facing, forward-facing, and boosters) are provided for an additional fee to ensure your family travels safely.

Ready to Reserve Your Ride?

Enter your passenger count, destination, and itinerary below for a quote.

Request a Custom Quote