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Sightseeing Cruises in Chicago

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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 Cruise Tickets

    The Chicago Architecture Foundation Center River Cruise follows the Chicago River through the Loop and along the lake, with licensed architect guides pointing out the city's landmark skyscrapers and design history. Find 90-minute standard cruise tickets, sunset session options, and evening cruise formats here.
    from $ 32.50

    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 $ 32.50

    Top experiences in Chicago

    20 experiences

    Free cancellation
    Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
    90-min Chicago River Architecture Cruise by Wendella
    Cruises
    $45
    90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 605 ratings.From $45
    Cruise boat on Chicago River passing under Clark Street Bridge.
    Official Chicago Architecture Cruise by First Lady
    Cruises
    $57
    Official Chicago Architecture Cruise by First Lady. Rated 4.8 out of 5 from 217 ratings.From $57
    Free cancellation
    Chicago River cruise boat passing under a bridge with city skyline.
    45-min Chicago River Architecture Cruise by Wendella
    Cruises
    from
    $28
    45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 953 ratings.From $28
    Tour boat on Chicago River with city skyline and bridge in background.
    75-Minute Chicago River Architecture Cruise by Shoreline
    Cruises
    from
    $39
    75-Minute Chicago River Architecture Cruise by Shoreline. Rated 4.5 out of 5 from 130 ratings.From $39
    Free cancellation
    Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
    90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
    Cruises
    $45
    90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.8 out of 5 from 119 ratings.From $45
    Free cancellation
    Fireworks over Chicago River with boats during dinner cruise.
    Chicago Fireworks Dinner Cruises
    Cruises
    from
    $112.10
    Chicago Fireworks Dinner Cruises. Rated 4 out of 5 from 4 ratings.From $112.10
    Free cancellation
    Fireworks over Chicago River with boats during dinner cruise.
    Chicago Fireworks Cruise
    Cruises
    from
    $54.76
    Chicago Fireworks Cruise. Rated 4.5 out of 5 from 8 ratings.From $54.76
    Free cancellation
    Odyssey Chicago River boat cruising on the Chicago River with city skyline.
    Odyssey Chicago River Architecture Dinner Cruise
    Cruises
    from
    $139.42
    Odyssey Chicago River Architecture Dinner Cruise. Rated 4.6 out of 5 from 47 ratings.From $139.42
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline at sunset.
    90-min Scenic Sunset Lake Michigan Cruise by Wendella
    Cruises
    $45
    90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 40 ratings.From $45
    Free cancellation
    Moored tour boats on the Chicago River at sunrise with city skyline.
    Chicago Architecture Evening Cruise by Shoreline
    Cruises
    from
    $46
    Chicago Architecture Evening Cruise by Shoreline. Rated 4.9 out of 5 from 38 ratings.From $46
    Free cancellation
    Tour boat on Chicago River with city skyline in background.
    Chicago River Architecture Cruise
    Cruises
    from
    $28
    Chicago River Architecture Cruise. Rated 4.8 out of 5 from 352 ratings.From $28
    Chicago River cruise boat with city skyline in the background.
    Chicago River & Lake Sightseeing Cruise by First Lady
    Cruises
    from
    $46
    Chicago River & Lake Sightseeing Cruise by First Lady. Rated 4.7 out of 5 from 3 ratings.From $46
    Chicago River cruise boat at night with city skyline in the background.
    Chicago at Night: River & Lake Sightseeing Cruise by First Lady
    Cruises
    from
    $50
    Chicago at Night: River & Lake Sightseeing Cruise by First Lady. Rated 0 out of 5 from 0 ratings.From $50
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline in the background.
    45-Min Lake Michigan Tour by Shoreline
    Cruises
    from
    $32.50
    45-Min Lake Michigan Tour by Shoreline. Rated 4.8 out of 5 from 12 ratings.From $32.50
    Free cancellation
    Sea Dog Cruise boat on Lake Michigan with Chicago skyline in the background.
    Chicago Sea Dog Architecture Cruise
    Cruises
    from
    $47.60
    Chicago Sea Dog Architecture Cruise. Rated 5 out of 5 from 1 ratings.From $47.60
    Free cancellation
    Tour boat on Chicago River with city skyscrapers in the background.
    Lake Michigan Cruise
    Cruises
    from
    $32.50
    Lake Michigan Cruise. Rated 4.8 out of 5 from 171 ratings.From $32.50
    Free cancellation
    Sea Dog boat cruising on Lake Michigan with Chicago skyline and Ferris wheel at dusk.
    Chicago Sea Dog Fireworks Cruise on Lake Michigan
    Cruises
    from
    $54.76
    Chicago Sea Dog Fireworks Cruise on Lake Michigan. Rated 5 out of 5 from 1 ratings.From $54.76
    Crowd on Chicago Haunted River "Creepy Cruise" by First Lady under moonlit skyline.
    Chicago Haunted River "Creepy Cruise" by First Lady
    Cruises
    from
    $46
    Chicago Haunted River "Creepy Cruise" by First Lady. Rated 0 out of 5 from 0 ratings.From $46
    Chicago River cruise with tourists viewing downtown skyscrapers.
    Chicago River Architecture Cruise
    Cruises
    $37
    Chicago River Architecture Cruise. Rated 0 out of 5 from 0 ratings.From $37
    Free cancellation
    Tour boat near Chicago's Navy Pier on a sunny day during the Chicago Skyline Lake Tour.
    Chicago Skyline Lake Tour
    Cruises
    from
    $32.50
    Chicago Skyline Lake Tour. Rated 4.5 out of 5 from 35 ratings.From $32.50

    How Headout makes choosing experiences effortless

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    We curate the best ways to experience
    We partner with the best
    All the best options, in one place
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    What our guests say

    Naomi W

    United States
    Couple
    2 weeks ago
    Claudia, the docent and guide was FABULOUS! Not only was she knowledgeable, but she shared info and history with lots if enthusiasm. You couldn't help but be excited and impressed by the range and backstreet of the buildings and their designers. A must-see tour!

    Official Chicago Architecture Cruise by First Lady

    Caroline H

    United States
    Couple
    2 weeks ago
    My 1st time to Chicago, everyone I talked to who'd been there mentioned the Architecture Tour was a must. They were not wrong! The guide was a great mix of really intersting information and light humor so the 90 minutes flew by.

    90-min Chicago River Architecture Cruise by Wendella

    Asha M

    United States
    Solo
    3 weeks ago

    +3 more

    Explanation was excellent. I loved the way he interacted with people. Lot of laughing! We waved people besides the river and it was fun. And the view was incredible!! A beautiful city!

    90-min Chicago River Architecture Cruise by Wendella

    Gomes L

    Group
    3 weeks ago
    Only a cruise like this one lets you take such beautiful photos of Chicago at night. Beyond the cruise itself, there was a great atmosphere on board thanks to the wonderful crew. I highly recommend it!

    90-min Scenic Sunset Lake Michigan Cruise by Wendella

    Justin B

    Solo
    May 2026
    Honestly the cruise was great but the guide Scotty D was incredible. He was fun, knowledgeable, and engaging. The cruise was a good mix of architecture and lake views, timely, and comfortable.

    90-min Scenic Sunset Lake Michigan Cruise by Wendella

    Nakisha A

    United States
    Couple
    3 weeks ago
    I absolutely loved the view, the food, and the drinks...everyone was so friendly and welcoming...I've never had dinner on the water so that was definitely a great experience, I took my fiancé for his bday and he never been there so that was great seeing his face and how much he loved it 🥰

    Odyssey Chicago River Architecture Dinner Cruise

    Lisa W

    United States
    Solo
    3 weeks ago

    +1 more

    Very nice overview about the architecture and history of Chicago combined with amazing views from both River and Lake. Tess was an amazing narrator and answered all questions, perfect combination of Information and humor

    90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

    Nephateria L

    United States
    Solo
    May 2026
    The experience was more than amazing. I'm from out of town and learned so much about Chicago and its history. The tour guide was phenomenal. The river, the buildings and architecture was beautiful. I would highly recommend going if you haven't.

    45-min Chicago River Architecture Cruise by Wendella