Private Chicago Extended Highlights Driving Tour

Our Bestselling Tour

See the Important Sites in Chicago in 4 Hours

Extremely Flexible Itinerary

Take Your Time Wandering Around Chicago

This tour expands upon the Private Chicago Highlights Driving Tour and proceeds at a more leisurely pace, allowing you more time to linger at attractions that interest you most and take as many photographs as your heart desires. Your guide will customize this tour to your liking, so please do not hesitate to speak up about what you want to see or do.


See all major Chicago attractions

Private tour in a sedan, SUV, or minivan depending on group size and availability

Admire Chicago’s skyscrapers and other architectural gems at your own pace

Local guide with a wealth of knowledge about the city

Customize your tour by letting your guide know what you want to see

Perfect option for those that want to take numerous photos

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Trip Details


Languages Available:

English, Spanish, Portuguese
Please indicate your preferred language upon booking.

Departure Time:

9 a.m. & 2 p.m. from April 1st to October 15th
10 a.m. from October 16th to March 31st

Meeting Point:

Hotel pick-up and drop-off available within these areas: Magnificent Mile, River North, River East, the Loop, the Gold Coast, Lincoln Park, Streeterville, South Loop, West Loop.


Year-round, every day (except 15-31/May, 1-3/Jun, 04/Jul, 23-31/Aug, 1-8/Sep, 13-19/Sep, 9-11/Oct, 20-29/Nov, 10-15/Nov, 2-7/Dec and 24-31/Dec)

Tour Duration:

4 hours

Group Size:

Minimum 1 person, maximum 9 people

Participation Requirements:

Children ages 4 and under are required to sit in a car seat. We have suitable car seats available for rent at $20 per tour, though parents are welcome to bring their own. Children ages 4 to 8 are required to sit in a booster seat, which we offer free of charge; please indicate this special request upon booking.


  • Private transportation around Chicago
  • Private driver/tour guide
  • Tips
  • Water

What to Bring:

  • Snacks
  • Camera

Good to Know:

Please note that while the driver is also your tour guide, they will be unable to leave the car at certain attractions. There will be stops on the tour where the guide will give the guests time to walk around and see the attraction themselves. After the allotted time, they should return to the meeting point and continue the tour.

Overview of the Tour

The Private Chicago Extended Highlights Driving Tour is our bestselling tour. As with all of our tours, it is private and includes a private vehicle and driver/guide, making the issue of transportation incredibly easy and comfortable. You’ll see all of the well-known attractions that tourists come to Chicago to see, including the Magnificent Mile, River North, South Loop, Streeterville, Gold Coast, and more! Since this is an expansion on the Private Chicago Highlights Driving Tour, you will appreciate the same sightseeing opportunities, but at a slower pace. You have the chance to really savor your time in Chicago and at the attractions that you enjoy the most.

Terms & Conditions

  • The passenger must be present at the meeting point within 20 minutes of the scheduled time. After this grace period, we will consider it a no-show, unless we are given prior notice.
  • Please note that the tour begins at the scheduled time, not when the client appears; if a client is late, that time will be counted as tour time.
  • This service has a 100% penalty for cancellation after reservation.
  • Date and time changes will not be allowed after confirmation of purchase. In extremely rare cases, we will change the type of vehicle or driver at the last minute, if the company determines some sort of potential risk, internal or external, for our passengers or in the case of an emergency.
  • For hotel pick-up: most hotels in Chicago do not have loading zones at the entrance, and in many cases, the guide will not be able to find the passenger in the hotel lobby. For this reason, the guide will be waiting for passengers inside or in front of the car. The vehicle can be identified by our company’s logo displayed in the window of the car.
  • If you have trouble locating your driver, please call our on-call phone number: +1 (312) 361-1153, extension 7. This is intended for emergency use and can be used at any time, day or night.

There isn’t much walking at all on this tour. There will be a couple of stops for guests to get out of the car to explore the point of interest and take pictures.

Your guide will be waiting outside your hotel either in front of or inside the car with our logo displayed in the window. If you have trouble locating them, please call our on-call phone number: +1 (312) 361-1153, extension 7.

We welcome anyone on this tour — young children, elderly guests, etc.

As this tour is relatively short, there will not be any stops for refreshments.

This tour focuses on the most famous parts of Chicago, yet it is quite customizable. The tour guide will evaluate what the guests wants to see and plan accordingly.

This tour is taken at a slower pace, making it ideal for those that like to take a lot of pictures or want to linger in certain places.


See More of Chicago!