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Chicago Tours

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    • Top experiences in Chicago

    Free cancellation
    Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
    90-min Chicago River Architecture Cruise by Wendella
    Sightseeing Cruises
    $45
    90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 605 ratings.From $45
    Free cancellation
    Chicago River cruise boat passing under a bridge with city skyline.
    45-min Chicago River Architecture Cruise by Wendella
    Sightseeing Cruises
    from
    $28
    45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 953 ratings.From $28
    Free cancellation
    Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
    Odyssey Lake Michigan Dinner Cruise
    Dinner Cruises
    from
    $132.58
    Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 93 ratings.From $132.58
    Tour boat on Chicago River with city skyline and bridge in background.
    75-Minute Chicago River Architecture Cruise by Shoreline
    Sightseeing 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
    Sightseeing 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
    Cruise boat on Lake Michigan with Chicago skyline at sunset.
    90-min Scenic Sunset Lake Michigan Cruise by Wendella
    Sightseeing 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
    Sightseeing Cruises
    from
    $46
    Chicago Architecture Evening Cruise by Shoreline. Rated 4.9 out of 5 from 38 ratings.From $46
    Free cancellation
    big bus: chicago hop-on hop-off bus tour-1
    Big Bus: Chicago Hop-on Hop-off Bus Tour
    Hop-on Hop-off Tours Chicago
    from
    $49
    Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.7 out of 5 from 299 ratings.From $49
    Free cancellation
    Cruise boat on Lake Michigan with Chicago skyline in the background.
    45-Min Lake Michigan Tour by Shoreline
    Sightseeing 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
    Big Bus Chicago tour and Chicago 360 observation deck view.
    Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
    Combo
    from $76
    $68.40
    10% off
    Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.6 out of 5 from 461 ratings.From $68.40
    Free cancellation
    Family enjoying Chicago skyline view from observation deck.
    Go City Chicago Explorer Pass: Choose from 39 Attractions
    City Cards
    from
    $84
    Go City Chicago Explorer Pass: Choose from 39 Attractions. Rated 4.5 out of 5 from 2113 ratings.From $84
    Free cancellation
    Tour boat near Chicago's Navy Pier on a sunny day during the Chicago Skyline Lake Tour.
    Chicago Skyline Lake Tour
    Sightseeing 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

    We curate the best ways to experience

    We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

    We partner with the best

    Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

    All the best options, in one place

    Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

    Book with complete peace of mind

    Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

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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

    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

    Floretta P

    United States
    Couple
    2 weeks ago

    +1 more

    The staff is friendly and very nice. Wedding Anniversary and Husband birthday. As for me 14 yrs if chemotherapy enjoying life.

    Odyssey Lake Michigan Dinner Cruise

    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

    Wei J

    United States
    Couple
    3 weeks ago
    The observation deck is high enough to view the whole city, also close enough to the water/beach to enjoy the beautiful blues.

    Combo: Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets

    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