Private Tours

All private tours are fully customized to specific customer needs including; content, route, begin ,end, time, length and refreshment options – cost is variable based upon options chosen. Our tours include a full array of themed walking and bus tours or combination tours with multiple subjects including; history, architecture and popular culture. Our tour hosts are gifted storytellers and interject enthusiasm, energy and humor in their personalized presentations to all guests. We specialize in private tours for all groups including school groups K -12. Our primary learning modality it learning while HAVING FUN!

Chicago's Finest Tours is the perfect alternative for those groups interested in a truly unique and dynamic experience in the "Windy City".

Our tours provide the perfect customization of discovery, learning and entertainment!

All Private tours are customized packages that combine for our guests the perfect "tri-fecta" of tour content: History + Architecture + Pop Culture.

With the perfect "tri-fecta" of destinations all rolled into one! "Loop" + Pedway + River Walk

Our Private tours are perfect for all groups including; corporate outings (collaborative team building), school groups (educational & fun), social clubs, civic organizations, reunions, military, anniversaries and weddings.

All Private Tours content is customized and the tour experience can be further enriched by adding some of the following features; trolleys, dinner, lunch, brunch, cocktails, snacks - just about anything short of a "Blue Angel" fly over!

In addition, we currently offer two unique VIP private tours for all couples - click on VIP navigation tab above for more information:

More About Our Private Tours

All private tours are highly customized to meet the unique needs of each of our groups. All Tours are designed to be unique urban adventures and aimed to entertain all ages. They are designed with families in mind or groups of friends, school groups, co-workers or a little of everything.


“Work event to remember!”

5 of 5 stars - Reviewed 2-20-2016

I planned a private event for 20 people with Dan and it was amazing. We had a group from 23-40+ years old and everyone loved it. We went a week ago and the group is still talking about it and asking trivia to each other. Huge success!

Megan P
Chicago, IL

“Terrific tour, terrific tour guide, terrific event!”

5 of 5 stars - Reviewed October 20, 2015

Contracted with Chicago's Finest Tours for our company outing. Dan worked with us to customize a phenomenal tour. We had a great time and learned a lot in a fun way. Tour guide was very interactive and kept the whole group (18 of us) interested and engaged. The sites were beautiful. This great city of ours is full of architectural wonders and the history facts were interesting and pertinent to the tour. LOVED IT! I will recommend this tour to anyone - Dan will work with you to make it memorable and special.

Visited October 2015

“Such a entertaining & educational Family outing!! Exceeded our expectations!!”

5 of 5 starsReviewed October 19, 2015

About 30 family members were in town for a family wedding looking for something fun to do together during the day. We certainly hit the jackpot!! Dan was our guide, such an amazing person full of entertaining stories, educational facts, animated and made the information fun- all 30 of us payed attention! (ages 6-60+!!) He made it really worth our while. Many of us were from Chicago, yet learned so many new things! So much knowledge and so much passion, it was a blast! He was very flexible to our large group needs, bathroom breaks, snack/drink breaks, and extremely personable.

They exceeded our expectations!!! Would HIGHLY recommend this for large or small group parties looking for a fun & educational group activity in Chicago!!!


5 of 5 stars Reviewed July 2, 2013

Chicago's Finest Tours is awesome! I have been in the event planning industry for over 10 years and have never seen such and an enthusiastic well spoken guide. Dan and his team put together trivia and a walking tour for our group and our attendees could not say enough great things. With a small budget Chicago Finest Tours provided an unforgettable team building experience. We will definitely be hiring them again! Check out the rest of our Chicago history tours.

Carolyn Paradowski
CNA Insurance