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, car 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.

In addition to our public tours Walking (History, History & Architecture, River Walk, Pedway) – Bus (Premier Music, Roaring 20’s, Crime & Corruption, World’s Fair, Pullman National Monument & Chicago Essentials) and Car (Chicago Essentials), you may choose from some of the following popular themes or request your own specific theme:

  • Cultural Mile & Historic Hotel Tour 
  • Magnificent Mile & Gold Coast Tour
  • Pedway Pub Crawl
  • Pedway Brunch Tour
  • South Side Tour
  • North Side Tour
  • West Side Tour
  • Jewish History Tour
  • Chicago Tragedies Tour
  • Immigration Tour
  • Irish Heritage Tour
  • Chicago Sports Tour 
  • Springfield, IL Tour 

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

All Private Tour’s 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!

To request a private tour, send an email to Dan O’Connell – [email protected]


What others are saying…

“I ran into great difficulty booking a tour for 108 people due to the fact that almost every company I contacted wanted payment in advance. This was problematic from the perspective of a lack of recourse if the guides failed to show (which I’ve had happen before). Trip Advisor doesn’t make researching for large groups the easiest, but I finally took a chance and called their highest rated tour company for Chicago. I’m glad I did!

Mr. O’Connell was incredibly accommodating, and he and his fellow guides did a fantastic job of helping our bus drivers navigate the city while offering trivia (with gift cards as prizes), Chicago style popcorn, and a wide-array of historical knowledge of the city ranging from the humorous to the macabre. They arrived on time and made sure that we saw the sights from the bus as well as from the ground. If I travel with another group to Chicago in the future, there’s no doubt which company I will use!”


Dan was amazing. I’ve lived in Chicago for almost 40 years and took a custom private tour with Dan when friends came to visit. I saw and learned so many new things about the city I thought I knew. I can’t wait for more visitors to book again. I highly recommend Dan & Co. You won’t be disappointed.


Family Reunion Private Tour Was Great!

How lucky I was to find this Tour Company and Dan O’Connell using an Internet search as I planned family reunion activities for July 2016! On the front side, Dan was so easy to work with as we arranged for the size of the bus and the sites to see, focusing on the history of the city. Like most families we have some elderly family members and some with limited mobility so we needed a non-walking tour. Also, we were staying out in Oak Brook so we needed a tour that could pick us up at our hotel and let us off downtown for an afternoon of sightseeing on our own. Dan was very flexible and arranged for all of those needs and preferences. Over the course of our 3 hour tour we saw many sites and learned lots of fascinating information to go with them. Dan was easy to understand and made the effort to connect by eye contact and showed interest in all of our group – which maxed out the bus’s 38 comfortable seats. And with the bus full, this made the price very reasonable per person. Finally, even at the end of the tour Dan was flexible as to our ending point(s) – which were 2 spots because of course like all families, not everyone wanted to eat in the same place. Thank you Dan – and also Juan our very pleasant and safe driver!


Private Van Tour the Best!

I considered a Hop On-Hop-Off tour for your group of 12 sisters/daughters but wanted something more personable and more suited to a group our size. I called Chicago’s Finest Tours and Dan immediately offered a personalized tour that would meet our timetable and our interests! He and his driver arrived at our hotel early and definitely had their act together! Dan was knowledgeable, personable, and passionate about all things Chicago and mixed together history, culture, a little architecture, sites, life in Chicago and a little trivia game while our driver navigated us through Chicago center and the near North and South communities. I would highly recommend Chicago’s Finest Tours.


Custom Bus Tour

Chicago’s Finest Tours was the perfect way for me to show off my beautiful city to family visiting from France. I was hosting about 15 aunts and uncles who were in town for my sister’s wedding and wanted a way to show them around the city without having them walk around too much. Dan worked hand in hand with me to provide a custom tour of the downtown area as well as the north and south sides of Chicago. We had a four-hour tour which felt like the perfect amount of time to see everything. The bus was large enough to see the buildings and we did not feel like it obstructed the views at all. Dan sat with us at the front of the bus and gave us tremendous information and facts about the sights around us, all with letting me enough time to translate all he was saying to my family in French. Dan’s knowledge of the city is unparalleled, he seemed to have answers for all of our ridiculous questions. My family could not stop talking about how wonderful the tour was for the remainder of the weekend. I would not hesitate to book another large tour with him in the future and will definitely be coming back for some smaller and more intimate tours of the city. Thanks again!



Please contact us to book a private tour.

Please call us to make a reservation if you are using a pre-paid voucher or gift card.