Chicago Private Custom City Tour With Hotel Pick Up

Matthew and Ben were the best tour guides my group and I could ask for during our stay in Chicago. We were picked up promptly at our hotel, which was extremely important. The private experience in a very spacious vehicle ensured we were comfortable. Both shared extensive knowledge of the city and points of interest. We also enjoyed great authentic Chicago hot dogs. Thank you for an incredible experience!!!

This is a nice tour for a small group to get an overview of Chicago. The hotel pickup makes it an easy trip. The combination of driver and tour guide made navigating simple.

This was a great way to see the city the way you want. Our tour guide, Sofia, and our driver, J T were great and gave us lots of information. If you are in Chicago for the first time, I highly recommend this tour.

Matthew is a knowledgeable tour guide. I will definitely recommend this tour.

We were with Matt as our guide and Vic as our driver. Matt’s love for Chicago is apparent in how he goes about his work…more than willing to answer any and all questions, consistently checking in to see if we were ok, and even giving my fiance a hard time for being a Packers fan. Despite heavy traffic from Lalapalooza, we were able to see the Bean, Navy Pier, stopped for some drinks and had an overall wonderful time. Would suggest for anyone who wants to have a personalized experience in Chicago and who wants a guide that really cares that you have a wonderful time.

Love, Love, Love this private tour. Matthew and TJ were great. VIP experience from beginning to end.

Seeing the city through the eyes of a local! Very informative and many small sound bites of local history. Not to be missed!

Matthew was exceptionally talented guide and good driver TJ made a great team. Highly recommend this tour!

Guide was very knowledgeable and made it fun. Saw a lot of great things and heard the backstories that were interesting.

Matt & Vic were sensational! Knowledgeable, humorous, down-to-earth and truly loved their city. They were on time, picked us up at our hotel and showed us all the site we wanted to see and so much more. Kind and compassionate assisting me with my walker. They told us some fascinating stories and interesting facts about Chicago . We learned so much and truly enjoyed every minute! I Highly recommend Viator and our hosts Matt and Vic. Book them now if you’re planning trip to Chicago. You won’t regret it😊

An excellent experience from start to finish. We were collected from our downtown hotel and driven around the city with Todd as our guide. Todd was extremely knowledgeable and told us all about the history and architecture of the city as we travelled around in comfort. We stopped at a few different places where we got out and walked around and took photos. Highly recommend this tour.

Great experience. Ontime and vey punctual. No complaints about this Tour. My clients enjoy it to the max.

Our family had a wonderful experience on our private tour of Chicago. From the moment we were picked up, everything was well-coordinated! Our guide was exceptionally knowledgeable, courteous, and attentive to every detail, and so was the driver! The vehicle was clean and comfortable, and the route offered a great balance of iconic landmarks, scenic views, and lesser-known local gems. An awesome way to experience Chicago as a family — highly recommended!

Todd Beckman was very informative, courteous and flexible for our private tour. The driver was also very safe and knowledgeable.

The guide was super knowledgable and the driver was so smart about which route would get us safely to our destination. We did this tour as soon as arriving to Chicago and we are so glad we did! Thanks for helping to make our Chicago trip memorable!!!

Scott is very knowledgeable, eloquent, and keep you interested throughout the driving in the streets of Chicago. He will tell you stories that will blow up your mind.

I recently took the private tour through the Magnificent Mile starting from Wrigley Stadium, and I have to say—it was absolutely phenomenal. From the Chicago Art Institute to Millennium Park, Wrigley Stadium, and even a stop by the House of Blues, this tour truly captured the essence of Chicago. The guides were incredible—true artisans of their craft. They didn’t just rattle off facts; they brought the city’s rich history to life in a way that was both digestible and deeply engaging. Their energy, humor, and passion for Chicago made the entire experience enjoyable and memorable. The pictures came out amazing, and my two fellow tour-goers and I had an all-around great time. If you’re looking to jumpstart your Chicago experience—especially in the downtown area—this is the tour to book. It was a blessing to explore the city this way. Can’t recommend it enough!

Our tour was enjoyable & entertaining. Excellent knowledge of the city & made it so much better by stopping by the site to chat about it before moving on to the next landmark.

Wonderful, friendly, knowledgeable Tour guide, Mike & driver, TJ. Picked us up at our hotel and dropped us off for our deep dish pizza lunch. Showed and told us so much about Chicago. Lovely tour bus, had water bottles, made bathroom stops, offered coffee stops and got us off the bus to see and tour special sights and for photos. Very enjoyable morning and our highlight of iur family trip to Chicago. Would highly recommend.

Matt (tour guide) and E (driver) were both great!!! I would highly recommend them! Thank you for a great tour and recommendations!

We had a great experience with Todd, not only is he a great tour guide but he is also a great photographer! He is so knowledgeable about the city and its history we recommend the this tour !

Really cool tour. Todd knew about pretty much everything we drove by (which TJ was making sure was as smooth and comfortable as possible). Options were given and our interests were considered. We'd been to Chicago several times, but all we saw and heard about was new to us. Can't wait to come back and revisit some of those sights. Thanks.

Awesome tour and the guide was very knowledgeable and entertaining. If this is your first time in Chicago, this is the tour you want to take.

Worth every penny!!! Such a fantastic experience discovering Chicago. Our guide, Todd, was excellent! We got the best pictures ever because he tells you where to stand.

The knowledge of Mike was simply outstanding !! TJ and Mike are a great team , my wife and I had plenty of laughs but also we learnt so much about the history of the city.

We liked our tour. We are a family of 4 with an 11 year old and a 10 year old. They did personalize the tour as we skipped out on the Wrigley field and opted to end the tour at the Sears tower. The host/speaker was very informative and kind. The driver was great as well. They gave us bottled water when needed and we walked around the bean area with our kids. The small van was very comfortable and spacious. Most of the tour is spent inside of the van. The tour was expensive, however, I would definitely recommend it and my family would use this company again, hands down! This was a very great day for us and beat walking! We learned a lot about Chicago!

Hotel pick up and drop off was very convenient! Our tour guide was extremely knowledgeable and informative. We learned so much about the city in such a short amount of time!

Our tour with Todd and our driver TJ was great! We got to see so many areas of the city and checked off many of the things we wanted to see in Chicago. Would definitely recommend to anyone visiting Chicago.

Our tour of Chicago was a ‘master class’ on the origins, history and development of an iconic American city thanks to Todd’s narration and T.J.’s adroit negotiation of the bustling traffic. A Chicagoan for 35 years, I learned things I never knew and saw parts of the city that I’d only heard about. Everything was so enjoyable and went so smoothly that I would consider an encore the next time our family and friends are in Chicago.

Mike and his team were absolutely wonderful to work with. They created a custom tour for all our east coast family and friends that were in Chicago for our son’s wedding. Todd our tour guide was funny, entertaining and extremely knowledgeable of all things Chicago. HIGHLY RECOMMEND

A very thorough, informative and enjoyable tour. Todd was an amazing guide- so very knowledgeable with an abundance of really interesting historical facts and stories. TJ was great too and very welcoming. I would recommend this tour to everyone. After 4 hours, I feel I know the city much better. Thanks guys!

We had a family event in town and wanted to see the city since it was our first visit to Chicago. We were anxious about the tour being cancelled since we had a blizzard warning the day before but there were no issues at all. Our guide Todd and driver TJ were on time and the van was perfect. We covered an incredible amount of the city and learned more about Chicago than we could have imagined. Todd shared his knowledge of the city and kept it very fun and interesting. We had a fantastic day! So glad we took the tour - it was definitely worth the time and money and I highly recommend Chicago Private Tours.

This truly was a one of a kind experience through Chicago. Both the driver and tour guide went up and above regarding customer service and the tour guide knew so much about the history of Chicago. He was impressive. We definitely recommend this tour for anyone who really wants to immerse themselves not only in the history, culture, and food but also stories we would not have the pleasure of hearing regarding Chicago. Thank you so much for making our Chicago trip one we will always remember.

Very knowledgeable tour guide, luxurious warm van and a friendly driver. What more do you want? It was perfect. 🤩

Relaxed and enjoyable tour around Chicago. Learned a lot about the history from our friendly and humourous guide Todd. Tour lasted about 4 hours and was flexible to include things of particular interest to us. A great way for us to get our bearings on our first day in Chicago.

Contacted them with exactly what I wanted. Single mom traveling with her daughter. I was VERY skeptical about everything we did while traveling alone. I portrayed this in the emails and phone calls. But I knew exactly what I wanted and needed. Mike took over and really went above and beyond to make this the best day trip ever! We had 1 full day in Chicago and we got to see and do so much! I gave him a list of everything I wanted to see and do and he added suggestions as well. We had a packed agenda but NEVER felt rushed. Riding around with our driver and Mike was like traveling with a best friend. My 9 year old daughter loved him and he answered all her questions and even played on the playground with her (oops he probably doesn’t want that getting out that he’s a softy). I felt safe and confident throughout the entire day. I would 100% recommend using this company ! Was worth every penny and more!

Great tour! Thank you we recommend it. Professionals. Picked us on time. My family and I loved the experience

Todd was great. We got on well and he was very patient with my son who is on the spectrum. We learned a lot, enjoyed the stops and saw things that even my kids were impressed by. I would recommend this service to anyone wanting a tour of Chicago.

I (39f), my mom (67yo) and my 2 kids (12yo and 13yo) really enjoyed this tour. Our guide was Todd and he put up with a lot of questions and wise cracks from a family of mixed ADHD, Autism, etc. I thought we may cut the tour short for the sake of my kids if they were bored or tired, but we went almost the full 4 hours with lunch in the middle. The driver (Harold) and Todd were very accommodating to our needs and very friendly. Chicago is filled with entertaining history, buildings, sights, etc, and we enjoyed them all!!

We enjoyed learning about the different types of architecture that has been used over the decades. We also enjoyed the blending of historical information and stories from the past with current information about what’s happening in Chicago now.

I had an amazing experience on this tour! Todd and his crew were super nice, polite, and very well prepared. They were also flexible in accommodating our particular sites of interest, which made the tour all the more enjoyable. I highly recommend this tour to anyone looking for a great time. Thank you Todd and crew for your wonderful hospitality!

We had the best time! Special thanks to TJ and Todd for showing us around. The tour was so complete and full of information about the history, architecture…amazing! I highly recommend it for any group that wants to enjoy the city. The minibus was spotless clean and water was provided! 5 stars isn’t enough to express how happy we were with this tour 😀

I highly, highly, recommend Chicago Private Tours if you want a relaxing touring experience of Chicago, I recommend asking for Todd and TJ.

Todd was the best guide ever and I manage a travel company Our contact Mike from Chicago Tours is incredible. I will recommend both to everyone

Came to Chicago with two other couples for a fun weekend with friends and decided to take advantage of an unseasonably warm weekend with some local sightseeing. I came across their website and Mike was great with working us into the schedule for a private two hour tour of the city. Our driver and guide were knowledgeable about EVERYTHING Chicago and the luxury sprinter van was comfortable for our entire party! Highly recommend this tour!

Well, this is the way to see Chicago. This tour provides all of the highlights of Chicago will plenty of time to top and soak it in. It is fast paced yet not hurried. I am a fan of private tours. For me, this is the best way to see a city. This was the best of many great private tours that i have experienced. I felt like a VIP. At the conclusion of the tour, I felt well acquainted with the City.

My husband and I did the classic city tour. Our guide Matt and driver Andrea were very nice and knowledgeable. It was very informative and entertaining. We were able to see the city in a short period of time. Would def recommend if short on time.

Everything went perfect. We were picked up on time, the guide (Todd) was very good and he took us around chicago explaining everyting very well. He was very ammusing and knowledgeble. the tour lasted more than what it was advertized and we all agreed it had been a success to have chosen this tour

Our guide, Todd, was super nice and knowledgeable. We loved being able to pick and choose where we go, for example we drove by the biggest Starbucks in the world (5 stories) and wanted to go in. So we stopped there and Todd went in with us for about 20 minutes. So fun! We asked to get dropped off at the Willis Tower after the tour (2pm) to go see the Sky Deck, but sadly they didn’t have tickets until 4:45pm which was too late for us. My only suggestion for improvement would be to let people know, if they want to go up, to buy tickets online at the start of the tour and then when they get dropped off there they can do it right at 2pm.