Top Chicago City Tours

Bookings are full, so get there at least a half hour before boarding to ensure you get seats together. Absolutely wonderful experience. Guide explains the history of buildings on the Chicago river then Boat goes to Lake Michigan for the sunset. You’re able to see Navy pier Hancock building, Sirrius (Willis) tower and many other Chicago landmarks coming back. The sky is beautifully lit.

Greg was the whole shabang!! He was funny, he was knowledgeable and he thoughtful about including everyone into the experience. We always take a food tour when we travel as we think its the best way to experience the city. This tour did not disappoint!! Thanks for the fun!

Absolutely worth it! The architecture tour was one of the highlights of our Chicago trip. Our guide was knowledgeable, entertaining, and made the city’s history come alive. The views from the river were incredible, and the whole experience was well organized and relaxing. Highly recommend!

This is a must for anyone like me who had never been to Chicago. Chicago is a beautiful city, and this was a great way to take it in. Floating down the Chicago River the guide dished out an insight to all these magnificent buildings that I could have heard nowhere else! If there is any negative side, such only came from a sore neck from looking up at all the majestic skyscrapers!

If you’re visiting Chicago, I cannot recommend the Chicago Walking History & Food Tour with Dash enough! It was hands down one of the highlights of our trip and the perfect way to experience the city beyond the typical tourist attractions. Our guide was incredibly knowledgeable, engaging, and passionate about Chicago’s rich history. Every stop along the way had a story that brought the city to life, making us appreciate not only its beautiful architecture but also the incredible people and events that helped shape it into the city it is today. We explored some of Chicago’s most iconic landmarks, including the city’s first public library, wandered through the beautiful Millennium Park, admired the historic elegance of the Palmer House, visited the massive Macy’s in downtown Chicago (which is unlike any department store I’ve ever seen!), and walked through the impressive Merchandise Mart while learning fascinating facts that I never would have discovered on my own. One of my favorite parts was that this wasn’t just a history tour—it was also a food adventure! We got to experience some of Chicago’s most famous foods exactly the way the locals enjoy them. From an authentic Chicago-style hot dog, to a delicious Italian beef sandwich, and of course ending with the legendary Chicago deep-dish pizza, every stop was absolutely delicious. It was the perfect way to sample the city’s iconic flavors without having to figure it all out on our own. What made this tour so special was how effortlessly it blended history, architecture, culture, and food into one unforgettable experience. The pace was comfortable, there was plenty of time to ask questions, take photos, and truly soak in everything around us. Whether it’s your first time in Chicago or you’ve visited before, I genuinely believe you’ll leave this tour with a much deeper appreciation for the city. We learned so much, laughed a lot, ate amazing food, and created memories we’ll always cherish. Thank you, Dash for giving us such an authentic, educational, and delicious experience. We would absolutely do this tour again and will be recommending it to anyone planning a trip to the Windy City! ⭐⭐⭐⭐⭐

This is a super informative tour made highly entertaining by John! He was hilarious and at the same time very knowledgeable. This tour included a time on Lake Michigan which included some spectacular views of the city skyline. Then on the river with all the architecture - overall great tour!

The Chicago Nighttime gangster brought Capone & Dillinger to life. Interesting well prepared tour. Rich history and fascinating stops at unique locations that tie to the history. Tour guide was skillful upbeat and carried the tour with energy and engagement

Hillary was our tour guide on the Chicago architecture boat tour, and she was absolutely wonderful! It was her first tour back for the 2026 season, and she was excellent. She was full of knowledge about Chicago architecture and history! The tour was so informative and fun!