City Highlights Driving Tour with a car & driver - ADVENTURES OF CITY GIRL

City Highlights Driving Tour with a car & driver


Tours by City Girl logo

Join me as we discover the city’s highlights on this Chicago tour with private transportation!

This is a great year-round tour.

From the Planetarium to Lincoln Park and everything in between. Being a local & tour guide for the last 10+ years, I know of all the best, must-see spots in the city! And I will show them to you with a car & driver.

You’ll discover where to get the BEST views of the city, one of the largest fountains in the USA, one of the surviving buildings from the Great Chicago Fire, a secret garden, a baseball park right in the middle of a neighborhood & more!

We will get out for short excursions at certain sights to stretch our legs and get a closer look. We can stop for a quick authentic Chicago lunch if you’d like.

I can’t wait to show you my beautiful city!

By choosing this tour, you will be supporting 2 small businesses! Thank you! A portion of each tour cost will be donated to My Block My Hood My City


We will explore downtown highlights and more with a car & driver:

– the site where the Great Chicago Fire started

– Museum of Science & Industry

– Garden of the Phoenix/Japanese Garden* (if weather, time & construction allows)

– admire the view from the Museum Campus

– Buckingham Fountain* (we’ll get a closer look from May-October)

– the Cultural Center*

– Millennium Park*

– drive by world-class public art on Dearborn St

– drive down the Magnificent Mile/pass the Chicago River

– Historic Water Tower District

– the Drake Hotel

– Lily Pool/Lincoln Park*

– Wrigley Field (on non-game days)

– the 96th Signature Lounge (875 N Michigan) The tour can end here if you like.

We will get out for short excursions at certain sights* to stretch our legs and get a closer look.

This is just an overall guide, and we will adjust it as needed depending on different factors (weather, time & construction). This price is based on my driver’s availability. If not, then the cost would increase and depend on finding an available car/driver. 

Pick up & drop off from your downtown Chicago hotel

Duration: 4 hours for 2 people

We will tour the city with a professional, insured car & driver. We’ll occasionally get out to stretch our legs and see things up close.

Extras include personal expenses, souvenirs & food, drinks, snacks



There are no reviews yet.

Only logged in customers who have purchased this product may leave a review.