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    1. Local experiences
    2. /All experiences
    3. /Chicago Illinois

    Best results for Chicago Illinois

    Showing 97-120 of 184 results
    4-Hour Sail & Swim Charter From Navy Pier
    Sailing

    4-Hour Sail & Swim Charter From Navy Pier

    Private Lake Michigan sailing with swimming, snacks, and a certified captain

    Private Lake Michigan sailing with swimming, snacks, and a certified captain
    5.0 • 27 reviews
    $1,417
    Chicago Sunset Sailing Cruise
    Sailing

    Chicago Sunset Sailing Cruise

    Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

    Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
    5.0 • 27 reviews
    $993
    Chicago Engagement Sailing Cruise
    Sailing

    Chicago Engagement Sailing Cruise

    A private sail for proposals, photos, and a champagne toast

    A private sail for proposals, photos, and a champagne toast
    5.0 • 27 reviews
    $887
    Chicago Sunset Skyline Sail
    Sailing

    Chicago Sunset Skyline Sail

    Sail Lake Michigan for views of Chicago’s shoreline and skyline

    Sail Lake Michigan for views of Chicago’s shoreline and skyline
    4.6 • 594 reviews
    $64/ person
    Chicago Blues Concert Sail
    Sailing

    Chicago Blues Concert Sail

    Live blues, Lake Michigan sailing, and Chicago skyline views

    Live blues, Lake Michigan sailing, and Chicago skyline views
    4.6 • 594 reviews
    $76/ person
    Chicago Sunset Skyline Sail
    Sailing

    Chicago Sunset Skyline Sail

    See Chicago’s skyline from Lake Michigan on an evening sail

    See Chicago’s skyline from Lake Michigan on an evening sail
    4.6 • 594 reviews
    $17/ person
    Watch Navy Pier Fireworks On A 90-Minute Cruise
    Boat Tours

    Watch Navy Pier Fireworks On A 90-Minute Cruise

    Cruise out for Navy Pier fireworks with skyline views and bar service

    Cruise out for Navy Pier fireworks with skyline views and bar service
    4.6 • 594 reviews
    $108/ person
    Navy Pier Fireworks Cruise in Chicago
    Boat Tours

    Navy Pier Fireworks Cruise in Chicago

    90-minute group sail for Navy Pier fireworks and Chicago skyline views

    90-minute group sail for Navy Pier fireworks and Chicago skyline views
    4.6 • 594 reviews
    $98/ person
    Charter a Private Yacht Cruise in Chicago
    Yacht Charters

    Charter a Private Yacht Cruise in Chicago

    Cruise Chicago by private 47 ft yacht with space for up to 12 guests

    Cruise Chicago by private 47 ft yacht with space for up to 12 guests
    4.6 • 116 reviews
    $1,696
    Drive an 18' Pontoon on the Chicago River
    Boat RentalsUp to 6

    Drive an 18' Pontoon on the Chicago River

    Cruise the Chicago River for 2 hours on a private, self-drive pontoon

    Cruise the Chicago River for 2 hours on a private, self-drive pontoon
    4.6 • 116 reviews
    $184
    Drive a 22' Pontoon Boat on the Chicago River
    Boat RentalsUp to 10

    Drive a 22' Pontoon Boat on the Chicago River

    Take the wheel on a 22 ft pontoon cruise on the Chicago River

    Take the wheel on a 22 ft pontoon cruise on the Chicago River
    4.6 • 116 reviews
    $544
    Drive a 2-Hour Chicago River Fireworks Pontoon Rental
    Boat RentalsUp to 10

    Drive a 2-Hour Chicago River Fireworks Pontoon Rental

    Self-drive pontoon on the Chicago River with Navy Pier fireworks

    Self-drive pontoon on the Chicago River with Navy Pier fireworks
    4.6 • 116 reviews
    $545& up
    1950s Boat Rental on Chicago River
    Boat RentalsUp to 6

    1950s Boat Rental on Chicago River

    Cruise Chicago’s river in a vintage 1950s Milo Craft

    Cruise Chicago’s river in a vintage 1950s Milo Craft
    4.7 • 475 reviews
    $559/ boat
    Chicago Night Kayak Tour
    Kayaking Tours

    Chicago Night Kayak Tour

    Paddle the Chicago River after dark with city lights and stories from your guide

    Paddle the Chicago River after dark with city lights and stories from your guide
    4.7 • 475 reviews
    $82/ kayak
    Chicago Skyline Kayak Tour
    Kayaking Tours

    Chicago Skyline Kayak Tour

    Paddle Lake Michigan’s shoreline for city views and guided instruction

    Paddle Lake Michigan’s shoreline for city views and guided instruction
    4.7 • 475 reviews
    $100/ kayak
    Explore the Chicago River on a 2-Hour E-Boat Rental
    Boat Rentals2

    Explore the Chicago River on a 2-Hour E-Boat Rental

    Pilot a 2-person Craig Cat and cruise the Chicago River skyline

    Pilot a 2-person Craig Cat and cruise the Chicago River skyline
    4.7 • 475 reviews
    $211/ boat
    3-Hour Chicago River Architectural Kayaking Tour
    Kayaking Tours

    3-Hour Chicago River Architectural Kayaking Tour

    Paddle the Chicago River and learn downtown architecture in 3 hours

    Paddle the Chicago River and learn downtown architecture in 3 hours
    4.7 • 475 reviews
    $82/ kayak
    Paddle a 3-Hour Chicago Fireworks Kayak Tour
    Kayaking Tours

    Paddle a 3-Hour Chicago Fireworks Kayak Tour

    Night kayak tour to watch Navy Pier fireworks

    Night kayak tour to watch Navy Pier fireworks
    4.7 • 475 reviews
    $82/ kayak
    Chicago River 1-Hour Kayak Rental
    Kayaking Tours

    Chicago River 1-Hour Kayak Rental

    Paddle the Chicago River past the Wild Mile and downtown skyline

    Paddle the Chicago River past the Wild Mile and downtown skyline
    4.7 • 475 reviews
    $43/ kayak
    Chicago River 2-Hour Kayak & Paddleboard Rental
    Kayaking Tours

    Chicago River 2-Hour Kayak & Paddleboard Rental

    Choose your paddlecraft for a self-guided outing on the water

    Choose your paddlecraft for a self-guided outing on the water
    4.7 • 475 reviews
    $87/ kayak
    Chicago River 2-Hour Kayak Rental
    Kayaking Tours

    Chicago River 2-Hour Kayak Rental

    Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

    Paddle past the Wild Mile and Chicago's skyline in a single or double kayak
    4.7 • 475 reviews
    $87/ kayak
    Chicago River 1-Hour Kayak & SUP Rental
    Kayaking Tours

    Chicago River 1-Hour Kayak & SUP Rental

    Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

    Explore Chicago River routes by kayak or stand-up paddleboard at your own pace
    4.7 • 475 reviews
    $43& up
    Chicago River 2-Hour Kayak Rental
    Kayaking Tours

    Chicago River 2-Hour Kayak Rental

    Paddle Chicago River routes in a single or double kayak

    Paddle Chicago River routes in a single or double kayak
    4.7 • 475 reviews
    $87/ kayak
    Chicago River 1-Hour Kayak Rental
    Kayaking Tours

    Chicago River 1-Hour Kayak Rental

    Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

    Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown
    4.7 • 475 reviews
    $43/ kayak
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