Chicago Travel Guides (Updated September 2026)

This is a great way to see Chicago and learn about the architecture from the building of the city to its current and future state. What made the trip was our guide who had us laughing and learning while seeing the amazing sites of downtown Chicago from the water. I highly recommend this tour.

We had a great experience. Our guide Kay was very knowledgeable with good sense of humor. Every detail was smooth and simple.

Fantastic sights, very knowledgeable guide. She also helped us take a photo with the skyline in the background. We went in Sept during the evening. Can get a bit chilly on the outside deck, bring a light jacket.

The guide was great but the 75 minute trip was pricey. It was worth it, though.

I think the architecture tour with Scotty D. was terrific. He knows his stuff very well and has an interesting way of presenting it. He adds humor and tongue in cheek sarcasm along the way. If I am correct, he is from Chicago, so he knows the city well and adds that information in his presentation. I went on this tour about 10 years ago. It was a shorter amount of time and not half as interesting. Scotty D. is definitely the guy you want to take.

Monica was the volunteer tour guide. She was awesome, knowledgeable, interesting and great sense of humor and storyteller. Wish we could give her a tip for her hard work!! 10 of us loved her, a group of family and friends.

Our tour guide, Grand, was fantastic. We learned so many fun facts and architectural history about Chicago's famous buildings, along with the spooky stories behind them. I highly recommend this tour—100% worth it, even for locals. I have lived here for a long time and still learned so many new things!

Excellent bus tour with MJ as our guide. He was funny, had lots of specific details, made it easy to understand, and added lots of fun facts about Chicago, we made two stops, one at theater where Dillinger was killed and one at Harry Carays where lots of mob artifacts were in the basement. Lots of fun, even on a Saturday night. Highly recommend.

Guide was fantastic. Sound quality was meh and the city is so loud so I missed things here and there but it still was great and I learned a lot and loved the ride.

Awesome boat Awesome tour narration Enjoyable tour Recommending it highly to everybody A must in beautiful Chicago city

Wow...the whole experience was without doubt one of the best things we've done to see and learn about a city's history! From the welcome crew, Cliff the guide (whose detailed lively narrative was just awesome), to the cruise itself. Honestly best value for money and will be booking again on any return trips to Chicago. Happy to recommend 👌

Great tour guide! Super well read

BOOK IT!! It was so fun! My husband and I enjoyed it. The most realistic experience ever. I would definitely book again.

Really enjoyed seeing Chicago from a new perspective! Our guide was shipper friendly and knowledgeable. Would definitely book another tour!

Our guide Richard was amazing - he was funny, informative, & engaging! Would definitely recommend to anyone visiting Chicago!

We had our tour with Scott and he did a wonderful job explaining everything and he was very engaging and made it very enjoyable!