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Top Chicago Cruises, Sailing & Water Tours

Cruises
  • Private Morning Sail On Lake Michigan New on TripHobo Duration: 2 Hrs

    Enjoy a private two-hour sailing charter for up to six people along Chicagos beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunnin...

    From
    USD384.79
  • Private Day Sailing Excursion On Lake Michigan New on TripHobo Duration: 2 Hrs

    Enjoy a private two-hour sailing experience for up to six people along Chicagos beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stun...

    From
    USD384.79
  • Private Chicago Sunset Sail On Lake Michigan New on TripHobo Duration: 2 Hrs

    Enjoy a private two-hour sailing experience for up to six people along Chicagos beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stun...

    From
    USD384.79
  • Private Navy Pier Fireworks Sail In Chicago New on TripHobo Duration: 2 Hrs

    Enjoy a private two-hour sailing experience for up to six people along Chicagos beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stun...

    From
    USD440.65
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    Spirit Of Chicago Lunch Cruise With Buffet New on TripHobo Duration: 2 Hrs

    With the sunshine reflecting off the lakefront, theres no better place to enjoy an afternoon in Chicago than aboard a Spirit lunch cruise. Departing from Navy Pier, Spirit of Chica...

    From USD74.66
    USD67.21
  • Save 7 %
    Chicago City Minibus Tour With Optional Architecture River Cruise 93 Reviews | Duration: Flexible

    Dont miss Chicagos famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable min...

    From USD35
    USD32.59
  • Save 10 %
    Chicago Odyssey Dinner Cruise 42 Reviews | Duration: 3 Hrs

    Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere a...

    From USD101.86
    USD91.69
  • Save 10 %
    Spirit Of Chicago Sunset Dinner Cruise With Buffet 77 Reviews | Duration: 3 Hrs

    Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Fi...

    From USD108.66
    USD97.81
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    Lake Michigan And Chicago River Architecture Cruise By Speedboat 154 Reviews | Duration: Flexible

    Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all about Chicago's history an...

    From USD42.5
    USD38.25
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    Chicago Odyssey Lunch Cruise 16 Reviews | Duration: 2 Hrs

    Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this 2-hour lunch cruise. While you cruise, a...

    From USD77.38
    USD69.66
  • Save 10 %
    Chicago Architecture River Cruise 2408 Reviews | Duration: 1 Hrs 15 Mins

    Experience one of the worlds most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River,...

    From USD43.68
    USD39.69
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    Lake Michigan Speedboat Ride 28 Reviews | Duration: 30 Mins

    Feel the need for speed? This exhilarating speedboat ride takes you out onto Lake Michigan for the ride of a lifetime. Experience the roar of the 2000-horsepower engines as you rac...

    From USD32.14
    USD28.93

About Chicago Cruises

Who doesn't love cruises? Experience extravagant cruise rides around . Pick the most popular cruise tours in and enjoy a panoramic view of the city.

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