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Guided Tours in Chicago

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    • Top experiences in Chicago

    7 experiences

    Free cancellation
    Chicago River cruise boat passing under a bridge with city skyline.
    Cruises
    45-min Chicago River Architecture Cruise
    from
    $28
    45-min Chicago River Architecture Cruise. Rated 4.8 out of 5 from 461 ratings.From $28
    Free cancellation
    Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
    Cruises
    90-min Chicago River Architecture Cruise
    $45
    90-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 293 ratings.From $45
    Free cancellation
    Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
    Cruises
    Odyssey Lake Michigan Dinner Cruise
    from
    $139.41
    Odyssey Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $139.41
    Free cancellation
    Tour boat on Chicago River with city skyline and bridge in background.
    Cruises
    60-Minute Chicago River Architecture Cruise
    from
    $44.43
    60-Minute Chicago River Architecture Cruise. Rated 4.4 out of 5 from 98 ratings.From $44.43
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline at sunset.
    Cruises
    90-min Scenic Sunset Lake Michigan Cruise
    $45
    90-min Scenic Sunset Lake Michigan Cruise. Rated 4.9 out of 5 from 17 ratings.From $45
    Free cancellation
    Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
    Cruises
    90-min Chicago River and Lake Michigan Architecture Cruise
    $45
    90-min Chicago River and Lake Michigan Architecture Cruise. Rated 4.7 out of 5 from 56 ratings.From $45
    Selling out fast
    Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.
    Willis Tower Skydeck Tickets
    Chicago Skydeck & Architecture Cruise with Small Group Guided Tour
    $129
    Chicago Skydeck & Architecture Cruise with Small Group Guided Tour. Rated 5 out of 5 from 1 ratings.From $129
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    Millions love heading out with us

    Sweta Joshi
    US

    Sweta

    United States
    Jan 2026
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    My mom is visiting Chicago for first time and taking her to the cruise and showing her the city was one of thing on my bucket list.

    45-min Chicago River Architecture Cruise

    Yera Suleiman
    US

    Yera

    United States
    Dec 2025
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    I enjoyed this so much that I did it twice during my trip, once at night and one during the day! The architecture around is so beautiful and the tour guides did an amazing job sharing its history.

    45-min Chicago River Architecture Cruise

    Chetna Dhembla
    US

    Chetna

    United States
    Dec 2025
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    +1 more

    I absolutely loved this tour! The JBL speakers were fantastic and made it so easy to hear the guide clearly, even in a busy and noisy environment. The tour guide was incredibly knowledgeable and shared information in such a fun, engaging, and effortless way that it really stayed with me. I still remember interesting facts like the Chicago River being 22 feet wide and how it turns green on St. Patrick’s Day. The clear sound from the JBL speakers and the amazing guide together made this tour truly memorable and enjoyable.

    90-min Chicago River Architecture Cruise

    Megan Mitchell
    US

    Megan

    United States
    Oct 2025
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    I had the best time with my grandfather on the cruise. He is older and struggles with mobility. This was the best way for him to see the city. Very relaxing. Our tour guide was extremely informative. #1 tourist attraction in Chicago

    90-min Chicago River Architecture Cruise

    Bebs Catherine Mediana
    US

    Bebs

    United States
    Sep 2025
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    The tour gave us an amazing experience and a picturesque view of the Chicago architecture which is really awesome. Natalie the tour guide was the best! 😊

    60-Minute Chicago River Architecture Cruise

    Barbara Stender

    Barbara

    Aug 2025
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    +2 more

    I thought the tour was perfectly guided, educational and beautiful! The seats were nice, the tour guide was very witty and hilarious! I learned so much on our guide today.

    60-Minute Chicago River Architecture Cruise

    Janet Stache

    Janet

    Aug 2025
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    We are very happy that we did this cruise! I would say the best cruise I've ever made. Our guide Charlie was a major part in this though. Without him that would only have been half as good.

    Chicago Architecture Evening Cruise

    Suryanarayana Murthy Majji

    Suryanarayana

    Oct 2025
    I absolutely loved my experience on the Wendella Chicago River Architecture Cruise! The tour was both relaxing and educational, offering an incredible perspective of Chicago’s iconic skyline and its rich architectural history. Cruising through the river gave me a completely different appreciation of the city’s design — from the classic art deco buildings to the stunning modern skyscrapers. What I enjoyed the most was seeing the downtown view open up as we entered Lake Michigan — the panoramic view from the water was breathtaking. The guide was knowledgeable and engaging, making the entire journey both fun and insightful. A truly memorable Chicago experience!

    90-min Chicago River and Lake Michigan Architecture Cruise

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