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Guided Tours in Chicago

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    • Top experiences in Chicago

    8 experiences

    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline in the background.
    Cruises
    30-Min Lake Michigan Tour by Shoreline
    from
    $32.50
    30-Min Lake Michigan Tour by Shoreline. Rated 4.2 out of 5 from 11 ratings.From $32.50
    Free cancellation
    Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
    Cruises
    90-min Chicago River Architecture Cruise by Wendella
    $45
    90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 409 ratings.From $45
    Free cancellation
    Chicago River cruise boat passing under a bridge with city skyline.
    Cruises
    45-min Chicago River Architecture Cruise by Wendella
    from
    $28
    45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 648 ratings.From $28
    Free cancellation
    Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
    Cruises
    Odyssey Lake Michigan Dinner Cruise
    from
    $132.58
    Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 28 ratings.From $132.58
    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 by Wendella
    $45
    90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 63 ratings.From $45
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline at sunset.
    Cruises
    90-min Scenic Sunset Lake Michigan Cruise by Wendella
    $45
    90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 20 ratings.From $45
    Free cancellation
    Moored tour boats on the Chicago River at sunrise with city skyline.
    Cruises
    Chicago Architecture Evening Cruise by Shoreline
    from
    $46
    Chicago Architecture Evening Cruise by Shoreline. Rated 5 out of 5 from 26 ratings.From $46
    Free cancellation
    Tour boat near Chicago's Navy Pier on a sunny day during the Chicago Skyline Lake Tour.
    Cruises
    Chicago Skyline Lake Tour
    from
    $32.50
    Chicago Skyline Lake Tour. Rated 4.5 out of 5 from 35 ratings.From $32.50

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    We curate the best ways to experience
    We partner with the best
    All the best options, in one place
    Book with complete peace of mind
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    What our guests say

    Ariana V

    United States
    Solo
    Last week
    Funny and engaging tour guide. Lovely views, especially on the cruise at sunset. I learned so many cool facts and have shared them with my friends and family. Money well spent!

    45-min Chicago River Architecture Cruise by Wendella

    Martha P

    United States
    Couple
    Mar 2026
    The service, the tour guide, the route. Everything was wonderful. The food and beverage selection was really good. Even the restrooms were on point.

    45-min Chicago River Architecture Cruise by Wendella

    Irma M

    Group
    3 weeks ago

    +4 more

    I had the best experience ever ! Loved the courtesy of the personal, food was excellent! Drinks amazing, loved the view of the city of Chicago from the Oddyssey !!

    Odyssey Lake Michigan Dinner Cruise

    Chetna D

    United States
    Couple
    Dec 2025

    +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 by Wendella

    Suryanarayana M

    Group
    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 by Wendella

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