What To Expect

What‘s Included

Reviews

• Learned a lot about Chicago, super fun!

  905meganp,Mar 20, 2026

  - Review from Tripadvisor

  5.00

  David is awesome! Super knowledgeable and tailored it to our questions and interests. I learned so much and would totally recommend it!

• The best historical tour guide in all of Chicago!!

  P7366QKsydneyr,Mar 5, 2026

  - Review from Tripadvisor

  5.00

  I absolutely LOVE Dash’s tours! To date, I’ve been on three tours with him, and truly - each one is better than the last! Originally I brought my friend Celeste on the Downtown Chicago tour and it was her favorite part of her trip. I also went on this same tour last week with friends and had a total blast!! As a non-native Chicagoan, it’s really cool to learn more about the city I work in each day and Dash’s knowledge is pretty spectacular! I also attended another one of Dash’s tours in Hyde Park all about the World’s Fair. It was almost like stepping back in time. He painted a picture of what we would have experienced there in 1893, showed us old photos of the sites, and took us to some really beautiful locations. I would highly recommend his tours, especially if you love history. Dash’s charm and knowledge is unmatched!!

  

• If A Walking Tour Was An Album With All Hits

  jakeaQ3636NR,Mar 5, 2026

  - Review from Tripadvisor

  5.00

  This is the best, most engaging tour Ive ever been on, actually! Tour guides beats and enthusiasm dazzled me on almost every corner.

• If you're in Chicago you MUST take this tour

  294milesk,Mar 4, 2026

  - Review from Tripadvisor

  5.00

  Forget all the big-name tour companies, this is the walking tour you absolutely have to take if you want a better understanding of what makes Chicago such a unique and magical city, from its past as a site of indigenous trails and fur trading to its present as a mecca or art, commerce, architecture, music and culture. With wit and bottomless knowledge, David weaves together stories from across Chicago's 189-year history, chronicling how the Windy City was built and rebuilt through events like the Great Chicago Fire, 1893 World's Fair, prohibition, Great Depression, and postwar boom up through today when the city stands as a global tourist destination. Over what feels like a quick 2 hours David shows you iconic landmarks like The Bean and Millennium Park as well as public art displays while exploring the inside of buildings like the Chicago Cultural Center and former Marshall Fields buildings (wait until you see the historic Walnut Room), both of which feature incredible—and otherwise hidden in plain sight—stained glass Tiffany domes. Whether you're just in town for a short visit or a lifelong Chicagoan, you'll discover a new understanding for what makes the city special, and the tour provides amble opportunities to take photos, warm up inside and use the bathroom. I was floored by how enjoyable this tour was, can't recommend it highly enough!

  

• Totally worth it!

  monicamR8777TV,Mar 1, 2026

  - Review from Tripadvisor

  5.00

  Dave's tour was excellent. His knowledge of local architecture and Chicago history is outstanding. I learned more about this city on his tour than I did in my 12 years as a Chicago Public School student. Definitely do it.

• Loved the tour!

  kristybM1081VN,Mar 1, 2026

  - Review from Tripadvisor

  5.00

  I had such a wonderful experience on David’s downtown tour yesterday! I really loved that you truly get a sense of the historical forces at work that shaped Chicago into the city it is today. David obviously really loves Chicago and that infectious spirit really comes across in his tour, which makes it a step up from other tours I’ve been on. He’s really kind and conversational, which puts you at ease asking questions. He also has a lot of consideration for peoples’ needs, asking if anyone needs a bathroom or place to stop. This is the second walking tour I’ve done with David and as a repeat customer I will seek out other tours with him in the future. Thanks David!!

• Incredible tour, incredible tour guide! Recommend for tourists and Chicagoans alike!!

  U2937WIjeffg,Mar 1, 2026

  - Review from Tripadvisor

  5.00

  LOOK NO FURTHER FOR THE BEST CHICAGO WALKING TOUR! David’s downtown tour is a celebration of Chicago that weaves together history, design, and the people who call it home. In a breezy 2 hours, David expertly guided us through the Loop with wit, charm, and a seriously impressive knowledge base for all things Chicago. While this tour is perfect for tourists, even the most weathered Chicagoan would enjoy David’s mastery and perspective as he peels back layers of history hiding in plain sight. There are multiple opportunities for bathroom breaks and warm ups from the weather, all while marveling at the gilded age ornamentation of historic buildings and priceless Tiffany domes. I now have a new favorite ‘must-do’ recommendation for friends and family who visit Chicago: GO ON DAVID’S TOUR!

• A fresh take on old Chicago

  charlyh937,Mar 1, 2026

  - Review from Tripadvisor

  5.00

  A friend got tickets for us to go on the tour, and it was so much fun! I'm from Chicago, but I still learned a lot. Dave is such a sweet funny person and he knows so much about the city. The tour was exactly two hours and ended right on the riverfront. Whether you're from out of town or a local this during this tour you'll experience downtown with a whole new sense of wonder.

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

• A beautiful tour with an exceptional guide

  meatballb2026,Feb 28, 2026

  - Review from Tripadvisor

  5.00

  A beautiful tour with an exceptional guide who curates everything perfectly!!!! From someone who has a hard time paying attention Dave kept me interested the whole time and I was surprised how fast it went by(time flies when you’re having fun)! It was honestly a perfect tour! I learned cool facts and saw details of the city I wouldn’t have noticed otherwise. I highly recommend this tour for anyone wanting to learn more about the city!

  

  

  

  

  

  

  

  

• A top-tier tour for locals and visitors alike!

  julesibaby,Feb 28, 2026

  - Review from Tripadvisor

  5.00

  Even as a lifelong Chicagoan, I can honestly say that 100% of David's tour held new, exciting facts and surprises! His route was unique and engaging, and he is so knowledgeable about the city's history. He encouraged questions from the group and had bonus answers on top of those. While many tour guides can be rigid and stuffy, David was bright and playful and is clearly so passionate about what he does. He mentioned he can also do custom private tours and I look forward to exploring that as well. 11/10 would recommend!!!

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