Private Chicago Scenic Driving Tour: Explore Windy City
2 Ratings
Experience the best of Chicago on a private scenic driving tour. Explore the city's iconic landmarks and hidden gems with a knowledgeable local guide. Book now!
Duration: 2 hours
Cancellation: 1 day learn more
  • Wrigley Field - Tour of Chicago Cubs Stadium surrounding and taking of pictures.
  • Lincoln Park Zoo - Drive by Lincoln Park Zoo. This can be skipped or customized to your need.
  • Chicago History Museum - Drive by Chicago History Museum. This can be skipped or customized to your need.
  • The Magnificent Mile - Detailed information about magnificent mile will be provided by the guide while driving by.
  • Michigan Avenue Bridge - Drive by Michigan Avenue Bridge. This can be skipped or customized to your need.
  • Chicago River - Drive by Chicago River. This can be skipped or customized to your need.
  • Millennium Park - Tour of Millennium Park and taking of pictures at the Cloud Gate “The Bean” for memories.
  • The Art Institute of Chicago - Drive by The Art Institute of Chicago. This can be skipped or customized to your need.
  • Chicago Cultural Center - Tour of Chicago Cultural Center and taking of pictures for memories.
  • Route 66 - Historic Route 66 Begin Sign. This can be skipped or customized to your need.
  • Grant Park - Drive by Grant Park. This can be skipped or customized to your need.
  • Lake Michigan - While driving on Lake Shore Drive, you will have the opportunity to see the beautiful Lake Michigan and a view of Ferry Wheel, Navy Pier.
What's Included
  • Private transportation
  • Hotel/Other Location Pickup & Return (No Airports)
  • Bottled water
  • Private Chicago Scenic Driving Tour
  • Driving Tour-Guide
What's Not Included
  • Gratuities
  • No Airport Pickup/Drop-Off
  • Food is not included but tourist can be taken to any of the Chicago style Popcorn, Hotdog or Donuts.
Additional Information

Chicago, being a large city, boasts numerous activities and attractions. To explore the city efficiently, one needs the support of an informed local tour guide - and that’s where our services come into play. Your personal Scenic Driving Tour of Chicago will commence when our enlightened Guide/Driver collects you from your hotel or any given location, paving the way for the adventurous journey through the magnificent windy city.

  • A minimum of of one person, and a maximum of 3 people, is required for every booking.
Wrigley Field
1060 W. Addison St.,
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(2 Ratings)
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1 star
Nov 12, 2023
A must for every first-time Chicago visit - An unforgettable experience, I highly recommend Deen's private driving tour! Visited Chicago for the first time on a business trip, and booked the tour for the last day to look around in the city. I also had a Ventra card but this is a lot more flexible than walking and taking the public transport, you can also fit in a lot more into 3 hours than going on your own. Deen arrived at the hotel at the negotiated time exactly to the minute, and showed the most interesting parts of the city. We chatted for the whole trip, and regularly stopped here and there to let me take photos, and finished the tour at the Willis Tower skydeck (also highly recommended). His grey Mercedes is comfortable and clean, and he has a road plan ahead but you can also alter it to your liking. He is also available on WhatsApp with his phone number. This drive is something I'll never forget, and I'll recommend him to my friends, too, do not hesitate to book him for your next trip! (All the attached photos were taken during the tour, the sky view after.)
Review provided by Viator
Aug 22, 2021
Great tour - very flexible - My daughter and I had a very good time with Deen. Deen was very flexible and creative on the fly as we wanted to see different things a little off the beaten path. Deen was very flexible and adapted on the fly including the Blue Angels air show!
Review provided by Tripadvisor
Select Date and Tickets
up to 3 guests
April 2024