Headout logo. Link to home.
Help
4.8(556)

Cruises in Chicago

  • All
  • Sightseeing Cruises
  • Dinner Cruises

    • Top experiences in Chicago

    Selling out fast
    View from Willis Tower Skydeck in Chicago at sunset.
    Willis Tower Skydeck Tickets
    Chicago Night Tour with Skydeck & Architecture Cruise
    NEW
    $169
    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
    NEW
    $129
    Free cancellation
    Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
    Dinner Cruises
    Lake Michigan Dinner Cruise
    NEW
    from
    $121.65
    Free cancellation
    Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
    Dinner Cruises
    Odyssey Lake Michigan Dinner Cruise
    NEW
    from
    $135.31
    Free cancellation
    Odyssey Chicago River boat cruising on the Chicago River with city skyline.
    Sightseeing Cruises
    Odyssey Chicago River Architecture Dinner Cruise
    NEW
    from
    $176.32
    Free cancellation
    Tourists on Sea Dog Cruise on Lake Michigan with Chicago skyline in background.
    Dinner Cruises
    Sea Dog Cruise on Lake Michigan
    NEW
    from
    $42.79
    Tour boat on Chicago River with city skyline and bridge in background.
    Sightseeing Cruises
    75-min Chicago River Architecture Cruise
    4.4(96)
    Rated 4.4 out of 5.0 from 96 ratings.
    from
    $44.43
    Cruise boat on Chicago River passing under Clark Street Bridge.
    Sightseeing Cruises
    First Lady's Chicago Architecture Boat Tour
    4.9(40)
    Rated 4.9 out of 5.0 from 40 ratings.
    $56
    Free cancellation
    Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
    Sightseeing Cruises
    90-min Chicago River and Lake Michigan Architecture Cruise
    4.7(56)
    Rated 4.7 out of 5.0 from 56 ratings.
    $45
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline at sunset.
    Sightseeing Cruises
    90-min Scenic Sunset Lake Michigan Cruise
    4.9(17)
    Rated 4.9 out of 5.0 from 17 ratings.
    $45
    Free cancellation
    Chicago River cruise boat passing under a bridge with city skyline.
    Sightseeing Cruises
    45-min Chicago River Architecture Cruise
    4.9(346)
    Rated 4.9 out of 5.0 from 346 ratings.
    from
    $28
    Free cancellation
    Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
    Sightseeing Cruises
    90-min Chicago River Architecture Cruise
    4.9(239)
    Rated 4.9 out of 5.0 from 239 ratings.
    $45
    Download app section background

    Millions love heading out with us

    David Naibei
    US

    David

    United States
    Oct 2025
    5/5
    ‌
    review-image
    This was just a lifetime experience. It was like rediscovering the whole history of Chicago in less than a hour. Perfect date with my girlfriend. We learned a lot while having hun.

    45-min Chicago River Architecture Cruise

    Megan Mitchell
    US

    Megan

    United States
    Oct 2025
    5/5
    ‌
    review-image
    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

    Lou Ann Miller
    US

    Lou

    United States
    Oct 2025
    5/5
    ‌
    review-image
    ‌
    review-image
    Wendella Crusie was the best! Dave the tour guide was so entertaining, very knowledgeable and passionate about Chicago, his city. He made the tour more personable and made you feel involved. I highly recommend this tour company!!

    90-min Chicago River Architecture Cruise

    Bebs Catherine Mediana
    US

    Bebs

    United States
    Sep 2025
    5/5
    ‌
    review-image
    ‌
    review-image
    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! 😊

    75-min Chicago River Architecture Cruise

    Barbara Stender

    Barbara

    Aug 2025
    5/5
    ‌
    review-image
    ‌
    review-image
    ‌
    review-image

    +1 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.

    75-min Chicago River Architecture Cruise

    Janet Stache

    Janet

    Aug 2025
    5/5
    ‌
    review-image
    ‌
    review-image
    ‌
    review-image
    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

    Terry moore

    Terry

    Oct 2025
    4/5
    The view was exceptional! Wish the boat had priority boarding as an option. The boat was crowded. Overall the trip was memorable!

    90-min Scenic Sunset Lake Michigan Cruise

    Suryanarayana Murthy Majji

    Suryanarayana

    Oct 2025
    5/5
    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

    We've served 44 million+ guests and we are here for you

    44 million+

    Happy customers across 10,000+ experiences

    In the media

    Featured and recommended by the best brands

    24 x 7 help center

    Have a question? Live chat with local experts anywhere, anytime