Chicago Travel Guides (Updated September 2026)

Guide was great and the views amazing.

This is great tour to do with family, friends, or your partner. It was nice to get the history behind the different buildings and learn about the architectural styles. Our guide’s sense of humor reminded me of The Office; I loved it. It was chiller closer to Lake Michigan so bring a light jacket.

Easy booking excellent tour guide! Take the sunset cruise!! It was so beautiful to watch the natural light go down, and the the beautiful sky line light up!

As a 30+ year Chicagoan, this is fantastic for visitors and residents.

It was a really good tour. Anna did a great job. It lasts about 90 minutes and went out to make Michigan and then down the river.

Friendly,funny,fantastic views. Professional tour guide. Captain and deckhands are attentive no need to worry about safety. They give you freedom to get your 360 view above deck and below deck.

The tour was awesome. Easy to find starting point. Our guide, Winnie Westside was awesome. She kept us entertained throughout the presentation and made learning the history of the gangsters very enjoyable. We took our 11 and 13 year-olds and they enjoyed it although likely missed some of the jokes. It's also a great way to see some of the city you may otherwise miss. Highly recommend.

It was a lot of fun and informative . I really enjoyed myself learned so much history of Chicago....

Fantastic. The boat is so cool, loaded with historical pictures & neat firefighter memorabilia. Great info shared by narrator, Cliff! The whole team is great! Going through the Chicago River locks is cool, architecture awesome! Would do it again for sure!

I didn't know what to expect but I was surprised with the technology and excitement of the Flyover Chicago excursion. It's worth every penny.

Loved the architectural river tour. Gives you a little history of the buildings and the city. Also took the tour that included the skyline on Lake Michigan another time, which was great too!

The tour guide, Hillary, was marvelous in her knowledge and entertaining manner. Also impressed by her command presence keeping everyone safety conscience. Boarding location was off the beaten path. Better signage would have been helpful.

I thought the docent did a really great job talking about the buildings, I honestly thought I was just going to enjoy the view and looking at the buildings, but she had some great information in history about the buildings which typically I’m not interested. She did a great job making it very interesting.

We lucked out on the weather rain was forecast but it didn’t come until late afternoon and we were the first tour at 10 am. If it’s a cool morning bring a jacket. The best views are from the top open air deck. The lower deck has windows but fewer chairs so if it’s bad weather get there early. The tour guide we had did a wonderful job.

Very informational. Guide was entertaining, yet professional.

I have done other architectural tours. This one on the fire boat was great. It is a smaller boat so it’s less crowded. Easy access for a cocktail. Informed tour guide with a sense of humor. The boat is run by veterans which is pretty neat.