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Sightseeing Cruises in Chicago

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  • Dinner Cruises

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    1

    Tour boat on the Chicago River with downtown Chicago skyscrapers in the background.

    Wendella Cruises Chicago

    Since 1935, family‑owned Wendella Cruises Chicago has been sharing the city’s story from the water. Depart downtown for an architecture tour along the Chicago River, a scenic Lake Michigan cruise, golden‑hour sunset sail, fireworks voyage or private charter; each boat features climate‑controlled salons, open‑air decks and expert local narration.
    from $ 28

    2

    Chicago Riverwalk with 'Chicago's First Lady' tour boat passing by Marina City.

    First Lady Cruises Chicago

    First Lady Cruises Chicago operates a fleet of elegant boats; each with open‑air upper decks, climate‑controlled lower salons, upscale marble restrooms and a full bar. As the only official cruise partner of the Chicago Architecture Center, they deliver expert‑led river and lake sightseeing, enchanting sunset and fireworks voyages, plus fully customizable private charters for groups large or small.
    from $ 28

    3

    Boats and kayaks on the Chicago River with city skyscrapers in the background.

    Chicago River Architecture Cruises

    from $ 45

    4

    People on a boat deck viewing Chicago skyline at dusk with water and cloudy sky.

    Shoreline Cruises Chicago

    Shoreline Cruises Chicago operates the city’s largest fleet; 11 tour vessels and 7 water taxis-delivering architecture river cruises, skyline lake excursions, festive fireworks sails and custom private charters. Guests enjoy open‑air observation decks, fully climate‑controlled cabins and entertaining expert commentary on Chicago’s architectural heritage.
    from $ 44.43

    Top experiences in Chicago

    7 experiences

    Cruise boat on Chicago River passing under Clark Street Bridge.
    Cruises
    First Lady's Chicago Architecture Boat Tour
    $57
    First Lady's Chicago Architecture Boat Tour. Rated 4.9 out of 5 from 46 ratings.From $57
    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 4.9 out of 5 from 503 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 319 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
    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
    Tour boat on Chicago River with city skyline and bridge in background.
    Cruises
    60-min Chicago River Architecture Cruise
    from
    $44.43
    60-min Chicago River Architecture Cruise. Rated 4.4 out of 5 from 98 ratings.From $44.43
    Selling out fast
    Odyssey Chicago River boat cruising on the Chicago River with city skyline.
    Cruises
    Odyssey Chicago River Architecture Dinner Cruise
    from
    $147.62
    Odyssey Chicago River Architecture Dinner Cruise. Rated 4.9 out of 5 from 10 ratings.From $147.62

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    What our guests say

    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
    ‌
    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

    Charlotte Madueno
    US

    Charlotte

    United States
    Mar 2026
    The atmosphere was amazing. My husband and I were on vacation for my birthday and this cruise was the highlight of my trip. The staff and captain were amazing and the food was delicious. There was nothing better than the views, they were breathtaking!

    Odyssey Chicago River Architecture Dinner Cruise

    Fely Combs
    US

    Fely

    United States
    Feb 2026
    Very romantic, a lot of good options for appetizers, entrees and desserts. Not to mention their drink menus were excellent! Loved this experience with my husband.

    Odyssey Chicago River Architecture Dinner Cruise

    Wiss Jérôme

    Wiss

    Dec 2025
    It was an other aspect to see Chicago by the river and i really enjoy the speaker who well explain all the architectures of chicag during the 20th century. Even with this cold weather, the 60 minutes past quite fast. Hope that other visitors will enjoy like i do.

    60-min Chicago River Architecture Cruise

    Rodolfo Icaza
    PA

    Rodolfo

    Panama
    Nov 2025
    The Chicago architecture cruise is absolutely worth it. The views from the river are incredible, and the guides explain the history and design of the buildings in a fun, clear way. It’s relaxing, scenic, and one of the best ways to experience the city. Highly recommended.

    60-min Chicago River Architecture Cruise

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