Private Chicago Scenic Driving Tour: Explore Windy City

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
Highlights
  • Wrigley Field - Cubs fan? Tour Wrigley Field, the historic home of the Chicago Cubs and one of Major League Baseball’s oldest ballparks. The iconic red marquee at Wrigley Field is a perfect spot for capturing a memorable photo up close.
  • Lincoln Park Zoo - Drive by Lincoln Park Zoo, a beloved zoo in the heart of Chicago. Explore diverse animal exhibits, from majestic big cats to playful primates, and learn about wildlife conservation. Stroll through beautifully landscaped grounds, enjoy interactive experiences, and capture memorable photos at this historic, family-friendly attraction.
  • Chicago History Museum - Drive by the Chicago History Museum to uncover fascinating exhibits that bring the past to life. Discover artifacts, stories, and displays showcasing significant events and figures in history. This stop can be skipped or customized to your needs.
  • The Magnificent Mile - Feeling magnificent? Drive by Chicago’s Magnificent Mile, a vibrant stretch of Michigan Avenue known for upscale shopping, dining, and iconic landmarks. Explore historic architecture, luxury boutiques, and cultural attractions in the heart of the city. Capture memorable photos and immerse yourself in the energy of one of Chicago’s most famous districts.
  • Michigan Avenue Bridge - Drive by the Michigan Avenue Bridge. Admire stunning views of the Chicago River and capture memorable photos of this iconic landmark.
  • Millennium Park - Tour Millennium Park, Chicago’s urban oasis. Discover iconic landmarks like Cloud Gate, Crown Fountain, and the Jay Pritzker Pavilion. Enjoy beautiful gardens, art installations, and stunning cityscape views.
  • The Art Institute of Chicago - Drive by The Art Institute of Chicago to discover world-famous art collections and iconic masterpieces. Enjoy an enriching cultural experience at this premier art museum.
  • Chicago Cultural Center - Tour the Chicago Cultural Center, renowned for its stunning architecture, including the world’s largest Tiffany stained-glass dome. It hosts a variety of cultural events, exhibits, and performances, promoting arts and culture in the heart of Chicago.
  • Route 66 - Historic Route 66 Begin Sign. Embark on America’s Mother Road, Route 66, spanning from Chicago to Santa Monica, California, exploring iconic landmarks and the rich history of this legendary highway.
  • Grant Park - Drive by Grant Park to discover intriguing headless statues amidst beautiful green spaces and iconic Chicago landmarks.
  • Lake Michigan - While driving on Lake Shore Drive, enjoy the beautiful views of Lake Michigan and the Ferris Wheel at Navy Pier.
  • Museum Campus - Explore Museum Campus, featuring the Field Museum, Shedd Aquarium, and Adler Planetarium, with stunning views of the city skyline perfect for memorable photos.
  • Buckingham Fountain - Tour Buckingham Fountain, a historic landmark known for its impressive water displays and stunning views in Grant Park, Chicago.
What's Included
  • Private transportation
  • Bottled Water
  • Free Hotel/Other Location Pickup & Return within 5 Miles of Downtown Chicago Center
  • Driving Tour-Guide
What's Not Included
  • Gratuities not included, but appreciated
  • Additional charges apply for Airport/Other Location Pick-up and Drop-Off
  • Call or Text Tour-Guide to make Airport/Other Location Pickup or Drop-off arrangement if needed
  • 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.
Location
Wrigley Field
1060 W. Addison St.,
Cancellation Policy

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

Customer Ratings
5.0
(10 Ratings)
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Jim_b
Aug 20, 2024
Highly recommend! - Seen was the absolute best - kept things fun, lots of local knowledge and willing to craft the tour so you have the best time.
Review provided by Viator
Jcb32301
Aug 20, 2024
Best tour of Chicago! - Deen was a fantastic guide - took us to all the best places. Saw Lake Michigan, Wrigley Field, Millennium park, Museum Campus, Buckingham Fountain and the Lincoln Park Zoo area. Learned a lot and had a great time!
Review provided by Tripadvisor
Nickwg9636bq
Aug 11, 2024
Amazing in depth vip look at Chicago. - Truly amazing experience. We went like 1.5 hours over and never asked for more. My wife and I were taken to all the great spots. Was a real vip experience. You want to see the city in a up close and personal manner with a knowledgeable driver and tour guide. We even got to see them filming Chicago fire and visited Chicago pd site and mollys fictional bar from the Chicago tv shows. This is the man for the job. Thank you brother for the great time.
Review provided by Tripadvisor
M680wlvictorn
Aug 9, 2024
Good Tour-Deen - Deen did a very nice job providing a comprehensive tour for the limited time we had. He was very polite and respectful and punctual. It was exactly what we were hoping to accomplish.
Review provided by Tripadvisor
Passport786650
Jul 24, 2024
Chicago Fire Tv show set tour - Got exactly what we wanted! A tour of the tv show Chicago fire sets…the fire house, mollys & white palace grill. Fireman gave us tour of the house for free & it was amazing! Deen really came through with the perfect time.
Review provided by Tripadvisor
Passenger55723978381
Jul 6, 2024
Great tour of Chicago with Deen - Deen is a great tour guide! He picked us up at our hotel right on time and began the tour with an overview of the tour agenda. Deen is very knowledgeable about the city he loves, Chicago! He took us to several area sites, such as the museum campus, the architectural bean, Wrigley field, the zoo, and many other stops along the way. At each point, he narrated on the historical value or an interesting aspect about each site. We would highly recommend this tour and if you are able to have Deen as your tour guide, you will be in good hands. This is a great way to get a two hour introduction to Chicago. In addition, Deen pointed out different neighborhoods and recommendations on places to eat in each area.
Review provided by Tripadvisor
Kylee_r
Jun 26, 2024
Worth it! - Highly recommend! I was in town for work and wanted to squeeze in sight seeing for work. This tour was perfect for that! Incredibly relaxed, flexible and fun! Arrived on time, excellent communication and options to hop out at different spots to explore/snap pics and then jump right back in and move on to the next spot.
Review provided by Viator
Immnuel_f
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
Ssherman02
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
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