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  • 6 Best Places to Stargaze in the US for Dark Sky Views in 2026
  • Best 289

    things to do in Chicago, IL

    Showing 265-288 of 289 results
    Chicago Skyline Tiki Cruise

    Chicago Skyline Tiki Cruise

    Take in Chicago’s skyline from a floating tiki bar with a full bar on board

    4.2 • 218 reviews
    $42/ person
    Chicago Sunday Mimosa & Bloody Mary Cruise

    Chicago Sunday Mimosa & Bloody Mary Cruise

    See Chicago by water from a floating tiki bar with Sunday drink specials

    4.2 • 218 reviews
    $45/ person
    Chicago Sunday Mimosa & Bloody Mary Cruise

    Chicago Sunday Mimosa & Bloody Mary Cruise

    Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials

    4.2 • 218 reviews
    $45/ person
    Chicago River Fireworks Tiki Cruise

    Chicago River Fireworks Tiki Cruise

    Watch fireworks and Chicago sights from a floating tiki bar

    4.2 • 218 reviews
    $45/ person
    Chicago Skyline 2-Hour Fireworks Cruise

    Chicago Skyline 2-Hour Fireworks Cruise

    Watch Chicago fireworks from a floating tiki bar with a full onboard bar

    4.2 • 218 reviews
    $56/ person
    Chicago Tiki-Themed Private Yacht Charter

    Chicago Tiki-Themed Private Yacht Charter

    Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

    4.2 • 218 reviews
    $89/ person
    Chicago Luau Party Boat Charter

    Chicago Luau Party Boat Charter

    Private 50-foot charter with two decks, a waterslide, and an open bar

    4.2 • 218 reviews
    $131/ person
    Chicago River Private Boat Charter

    Chicago River Private Boat Charter

    Private river cruising with Bluetooth sound and beverage credits on longer charters

    4.2 • 218 reviews
    $30& up
    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

    4.2 • 218 reviews
    $89/ person
    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Celebrate on an 80-foot yacht with an included open bar

    4.2 • 218 reviews
    $89/ person
    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Tiki-Chic Yacht Charter From Chicago Riverwalk

    Private yacht charter with an included open bar and skyline charter option

    4.2 • 218 reviews
    $89/ person
    Chicago River Tiki Bar Charter

    Chicago River Tiki Bar Charter

    Cruise the Chicago River aboard a private floating tiki bar

    4.2 • 218 reviews
    $105/ person
    Chicago 50' Party Boat Charter

    Chicago 50' Party Boat Charter

    Private Chicago river and lake charter with an included open bar

    4.2 • 218 reviews
    $131
    Tiki Party Boat Charter in Chicago

    Tiki Party Boat Charter in Chicago

    Cruise Chicago’s river and lake skyline aboard a private two-deck party boat

    4.2 • 218 reviews
    $131/ boat
    Fall Hayride Cruise on the Chicago River

    Fall Hayride Cruise on the Chicago River

    Float through Chicago’s skyline on a festive fall hayride

    4.2 • 218 reviews
    $21/ person
    Chicago 30-Minute Jet Ski Rental

    Chicago 30-Minute Jet Ski Rental

    Ride Lake Michigan with downtown Chicago views

    4.1 • 188 reviews
    $104/ jet ski
    Ride a Jet Ski Near Navy Pier

    Ride a Jet Ski Near Navy Pier

    Jet ski on Lake Michigan with skyline and Navy Pier views

    4.1 • 188 reviews
    $104/ jet ski
    Northbrook Holiday Drive-Through Light Show

    Northbrook Holiday Drive-Through Light Show

    Drive through 2.5 miles of holiday lights, themed displays, and a laser show

    4.0 • 322 reviews
    $45/ vehicle
    Explore Logan Square Street Art & Murals Tour

    Explore Logan Square Street Art & Murals Tour

    Walk Logan Square murals and learn the artists behind them

    $37/ person
    Private Lincoln Park Zoo, Conservatory & Museum Tour

    Private Lincoln Park Zoo, Conservatory & Museum Tour

    Discover Lincoln Park’s nature and history with a local guide

    $292
    Private Navy Pier Fireworks Sailing Charter in Chicago

    Private Navy Pier Fireworks Sailing Charter in Chicago

    Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

    $1,007& up
    Parasailing Flight Over Lake Michigan in Chicago

    Parasailing Flight Over Lake Michigan in Chicago

    Parasail up to 500 feet above Lake Michigan for skyline views

    $147/ person
    4-Hour Chicago Sailing Charter

    4-Hour Chicago Sailing Charter

    Sail Chicago’s lakefront on a private charter with time to swim and relax

    $1,007& up
    Chicago Sunset Sailing Charter

    Chicago Sunset Sailing Charter

    Sail Lake Michigan at sunset for Chicago skyline views from the water

    $1,007& up
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