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Dive into the fun with water activities! From boat rentals to paddle boarding, these experiences are sure to make a splash. Time to get wet and wild.

experience

Sleek luxury white motor yacht docked at a tropical waterfront home with palm trees and a colorful sunset reflected in calm canal water.

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Wet Again Charters - Private Boat Rentals & Lake Adventures

4hr

From $1,600/party

experience

Party on the Lake! Playpen, fireworks, concerts & more for up to 13 guests image 1

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Group of friends relaxing on a sailboat deck docked at a sunny waterfront promenade in summer

Party on the Lake! Playpen, fireworks, concerts & more for up to 13 guests

5 (15)
2hr

From $900/party

experience

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Spacious white motor yacht cockpit with curved cushioned seating and fold-down helm seat under a canvas bimini, overlooking a busy dock with multiple boats at a tree-lined marina.

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Cozy luxury yacht cabin interior with polished teak flooring, warm wood paneling, beige leather lounge, and a forward V-berth bed dressed with navy cushions and an anchor throw pillow.

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Sunlit luxury blue-and-white motor yacht on turquoise water beneath a partly cloudy sky

Sleek white-and-blue motor yacht docked at a marina on a sunny day, calm green water and tree-lined shoreline in the background.

Sleek navy-and-white motorboat docked at an urban marina among other boats, with high-rise city skyline reflected in calm water on a sunny day.

Bow of a boat on the Chicago River pointing toward downtown skyline with glass skyscrapers, a historic riverside building with flags, and bright blue sky reflected in the water.

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White cabin cruiser with navy bimini top docked at a busy urban marina pier, blue fenders along the hull and a city skyline visible under a sunny blue sky

Eight women in swimsuits and sunglasses smiling and holding drinks aboard a sunlit motorboat under a navy bimini, turquoise water and other boats visible on a clear summer day.

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Silhouetted group on a boat watching bright orange fireworks burst over a glittering city skyline reflected on the water at night

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Sunset view of the Chicago River with boats cruising past illuminated downtown skyscrapers and reflective glass towers under a glowing sky

Four friends in black bikinis relaxing on a motorboat deck on a sunny summer day, wind‑tousled hair, holding canned drinks and phones and smiling with blue sky and water in the background.

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Smiling couple in swimwear relaxing on a boat with the Chicago skyline and skyscrapers over Lake Michigan on a sunny summer day

Group of friends laughing and posing on a boat in swimwear, with the Chicago skyline and lake in the background on a sunny summer outing.

Group of people swimming and lounging on blue noodles and a bright yellow float near anchored boats on Lake Michigan with the Chicago skyline in the background, summer boating scene

Nine friends smiling on the bow of a boat on Lake Michigan with the Chicago skyline under a partly cloudy summer sky

Bow of a white boat on the Chicago River with downtown glass skyscrapers and a historic riverside building under a bright blue sky.

Private Charters for Day Parties & Fireworks Cruises

5 (10)
3hr

From $90/person, $900/party

Explore your destination through the lens of someone who’s already been there done that!

experience

Chicago Party on Boats , FunTime! Up to 20 Passengers, BYOB, Unforgettable Fun! image 1

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Pontoon party boat with passengers enjoying a sunny summer day on clear blue water, sailboats and motorboats visible on the horizon

Chicago Party on Boats , FunTime! Up to 20 Passengers, BYOB, Unforgettable Fun!

3hr

From $1,630/party

experience

Group of women in colorful bikinis and sunglasses posing on the bow of a yacht during a sunny summer boat party in a crowded coastal bay

Three women in colorful bikinis celebrating on a boat with drinks and a smartphone, Chicago skyline and Lake Michigan turquoise water in the background on a sunny summer day

Three friends in bikinis laughing and holding canned drinks while lounging on a boat with blue water and an urban skyline under a sunny summer sky.

Three women relaxing barefoot on a yacht at sunset, smiling and posing with a city skyline and marina waterfront glowing in the background.

Two women in colorful bikinis lounging on the bow of a white yacht against a turquoise lake and modern city skyline under a bright blue sky

Two friends in swimsuits toasting drinks on a sunny boat ride on Lake Michigan with the Chicago skyline and skyscrapers in the background

Friends lounging on a boat bow at night watching vibrant pink, red and blue fireworks burst over a glowing city skyline with shimmering reflections on the water, one person wearing a yellow hat.

Aerial drone view of a white yacht with people sunbathing on the deck and a bright yellow-green inflatable mat trailing in clear turquoise water.

Group of people sunbathing and hanging out on a white yacht on turquoise lake water with a high-rise urban waterfront skyline and clear blue summer sky

Aerial view of a white motor yacht cruising turquoise water near an urban tree-lined waterfront and city skyline on a sunny day.

Sleek white motor yacht on turquoise water near a tree-lined urban waterfront and downtown high-rise skyline

White cabin motorboat on turquoise water near an urban waterfront with tree-lined promenade and high-rise buildings on a sunny day

Sleek white motor yacht floating on bright turquoise water beside an urban waterfront promenade with trees and parked cars

Sleek white motor yacht anchored in clear turquoise water near a sunlit coastal promenade with parked cars and pedestrians

Chicago’s Premier Boat Rentals - Private Lake Michigan Yacht Charters for Groups Up to 12

5 (16)
4hr

From $1,005/party

experience

Group of young adults in swimsuits popping champagne on a boat party with the Chicago skyline and Lake Michigan under a sunny blue sky

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Aerial view of a white-and-burgundy luxury motor yacht on clear turquoise water, sunlit teak deck with cushioned lounge area and swim platform.

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Sleek white luxury motor yacht docked at a sunny marina, blue water reflecting the hull with sailboat masts and docks in the background.

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Aerial view of a luxury yacht anchored in turquoise water with people lounging on a floating platform and nearby paddleboards

Six friends in swimsuits lounging on paddleboards and a large floating mat on bright blue water with a downtown skyline and beach in the background on a sunny day.

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Five friends laughing and clinking bottles on a yacht in bright summer sun, turquoise water with boats and the Chicago skyline of skyscrapers in the background.

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Private Skyline Cruise: Chicago’s Most Luxurious Yacht Experience

6 Reviews
4hr

From $130/person, $1,700/party

experience

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Group of women in colorful swimsuits posing on the stern of a white yacht with a bright green foam roll, docked at a busy marina with a city skyline and clear blue summer sky.

Group of friends lounging and waving on the bow of a white yacht with the Chicago skyline and Navy Pier Ferris wheel across Lake Michigan under a cloudy sky

Woman in a green dress posing on a boat bow at sunset with the Chicago skyline, glowing city lights, other boats on the water, and fireworks over Lake Michigan

Group of friends in white and neutral summer outfits posing on a wooden marina dock in front of a docked boat, waterfront skyline and wispy blue sky at golden hour.

Woman in a bright blue bikini posing on the bow of a white yacht, smiling with sunglasses on her head on a sunny day over turquoise sea with boats in the background.

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Chicago Yacht Party Charter, Birthdays & Bach Parties

5 (15)
3hr

From $127/person, $1,650/party

experience

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Ten friends smiling and posing on a yacht at a busy Chicago marina, with sailboats and the city skyline in the background under a partly cloudy sky.

Four friends in colorful bikinis cheering on a boat in Lake Michigan with the Chicago skyline and John Hancock Center in the background on a sunny summer day

Six friends relaxing on a yacht on Lake Michigan with the Chicago skyline and high-rise buildings in the background, sunny blue sky and dozens of pleasure boats nearby

Group of friends in swimsuits on an inflatable raft in Lake Michigan, raising drinks with downtown Chicago skyline and boats along the shoreline on a sunny day

Three women relaxing on the bow of a white yacht cruising the Chicago River, with the Chicago skyline and Willis Tower rising against a clear blue sky.

Group of five people lounging on a yacht bow with the Chicago skyline and sunburst over a downtown skyscraper, cruising Lake Michigan on a summer day

Chicago Bachelorette Yacht Party: Private Luxury Charter on Lake Michigan

6 Reviews
4hr

From $130/person, $1,700/party

experience

Three white motor yachts with people sunbathing on the bows, floating on turquoise lake water in front of a downtown skyscraper skyline under a clear summer sky.

Person lounging on a circular inflatable pool float in turquoise lake water with the Chicago skyline and waterfront Ferris wheel visible across the bay.

Three sleek yachts cruising on bright blue Lake Michigan with the Chicago skyline of skyscrapers towering behind on a sunny day.

Three luxury yachts cruising on golden Lake Michigan at sunset with the Chicago skyline and a dramatic pink-orange sky.

Three luxury yachts moored at a downtown marina at night, glowing skyscrapers and colorful city lights reflecting on calm water.

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Comparison chart for downtown Chicago boat charters showing a checklist-style graphic: left column with green checkmarks for included amenities (prime downtown pickup, no-haul ice, floating islands/water toys, wireless charging, complimentary items, real restroom focus, premium Bluetooth audio, hosted crew, towels, padded sun lounges); right column uses warning triangles and red Xs to show these features are limited or rare on typical Chicago charters.

Chicago’s Most Complete Yacht Charter & Party Boat Experience

5 (11)
4hr

From $100/person, $1,200/party

experience

Group of seven adults posing on a boat cruise in bikinis and sunglasses, smiling on a sunny summer day over turquoise tropical ocean water.

Two friends in bikinis and sunglasses striking a playful pose on a motorboat deck with the Chicago skyline and blue sky in the background.

Friends lounging on a white motorboat in turquoise water under a bright blue sky with puffy clouds, summer boating scene

Group of friends in bikinis enjoying a boat party on Lake Michigan with the Chicago skyline and yachts in the background.

Group of friends in swimsuits enjoying a summer boat party on a white motor yacht in a busy Chicago, IL marina under a bright blue sky

Friends partying on a yacht near a city skyline, lounging with drinks while others float on blue foam mats in choppy lake water.

Group of friends in swimsuits enjoying a boat party on the bow of a motorboat in turquoise coastal waters, taking photos and sipping drinks under a dramatic cloudy sky with other boats nearby.

Group of friends smiling on the swim platform of a white motor yacht docked at a Chicago marina, transom reading 'No Bad Days, Chicago, IL' under a partly cloudy summer sky.

Group of women in bikinis enjoying a sunny boat party on Lake Michigan with the Chicago skyline and blue sky in the background

Group of friends on a white motor yacht anchored off Chicago, IL, lounging, sunbathing and swimming on a sunny summer day

Party on Lake Michigan: Downtown Chicago Yacht Charter

5 (10)
3hr

From $1,100/party

experience

Thatched-roof party boat cruising coastal waters with people on the sunlit upper deck, sailboats dotting the horizon for a lively summer boat tour vibe.

Collage of a lively Chicago River boat party: tiki-style double-decker riverboat with blue slide by the downtown Chicago skyline, a group of friends in Hawaiian shirts posing inside, a woman in white cheering on the bow, and the boat passing under a bridge on the Chicago River.

Chicago River skyline with glass skyscrapers, a low bridge and a tour boat on rippling water under a bright blue sky

Tiki-themed party boat docked at an urban lakefront with a rooftop crowd, bright blue water slide, American flag, and downtown skyline in the background on a sunny day.

Tropical-themed party boat with a thatched roof and blue waterslide on Lake Michigan with the Chicago skyline in the background

Chicago’s Premier Tiki Party Boat: Bar Package Included + Slide

Instant Book

5 (10)
3hr

From $110/person

experience

View from a sailboat bow over teak deck into turquoise harbor, three yachts tied side-by-side, sun glinting on water, people relaxing on neighboring boats and a distant city skyline under a bright blue sky with fluffy clouds.

Sunlit person in a blazer and sunglasses steering a sailboat helm under an American flag, cruising on calm blue open sea from the yacht's cockpit.

Sailboat interior salon with teal curved seating and wooden table decorated for a bachelorette: gold "bride" balloons, inflatable ring balloons, gift bags, scattered confetti, backpacks and sneakers.

Chilled champagne bottle with an orange label standing on a teak yacht deck, sunlit blue sky and blurred nautical flags in the background

Sailboat with American flag anchored on Lake Michigan near the Chicago skyscraper skyline, paddleboards in the foreground and dramatic cloudy sky overhead.

Bright cruising sailboat interior with warm wood paneling and teak floors, compact galley with double sink and stove, cozy turquoise U-shaped settee around a foldaway dinette, porthole windows and built-in storage.

Playful person in a blazer stretching legs across a sailboat cockpit while clutching the helm, calm ocean and an American flag at sunset.

Sunlit sailboat sporting an American flag, bobbing on shimmering green water with a modern downtown skyline in the background.

Top-down view of a yacht's aft teak swim platform and folding boarding step tied with ropes, set against rippling deep-blue sea — ready for a swim.

Group of friends posing on a sailboat deck, enjoying a sunny day on coastal waters with mast and flag against a blue sky

Golden sunrise glinting over a calm open ocean, sunlight reflected on rippled water with a rocky shoreline in the foreground

Cozy sailboat cabin interior — glossy wooden dining table and teak floor, green cushioned seating, compact galley with sink and portholes, storage and cooler in a warm yacht salon.

Aerial dusk view of the Chicago lakefront and high-rise skyline with a marina of moored sailboats, a distant Ferris wheel on the pier, and a red arrow labeled “Guppy” pointing to a small boat.

Four smiling women in colorful bikinis and sunglasses posing together on a sailboat deck with clear blue sky and ocean in the background — sunny summer boating vibe.

Silhouette of a person standing on a sailboat deck with arms raised, Chicago skyline glowing at dusk across Lake Michigan

Flyboarder propelled above turquoise water beside a sailboat with a rainbow flag, with downtown Chicago skyline and high-rise buildings on a sunny lakefront day.

Smiling man in a wide-brimmed hat and navy blazer standing on a sailboat at a sunny marina, holding the boat's railing with blue sky and calm harbor water in the background.

Sleek black sailboat moored at a busy city marina, turquoise water and skyline under a bright, partly cloudy sky.

Sailboat summer party on Lake Michigan with Chicago skyline in the background, friends in swimsuits, paddleboards and colorful inflatables, American flag flying

Smiling woman in sunglasses leaning on a sailboat rail with a drink, American flag waving and a city skyline over blue water on a sunny day

Person in a white swimsuit on a sailboat holding a pink heart-shaped float and wearing heart sunglasses, with turquoise Lake Michigan, a paddleboarder nearby and the Chicago skyline under a bright summer sky.

Smiling woman on a sailboat deck at a sunny marina, wearing a gray cap and light shorts, giving two thumbs up with other boats and docks in the background.

Sailboat with a large peace-sign sail gliding on teal water at sunset with the Chicago skyline and other sailboats under a dramatic cloudy sky

Night sailboat cockpit with red-lit cabin, deck rigging and seating in the foreground and an illuminated city skyline reflected on the water in the background.

Six friends in swimsuits posing on a sailboat at sunset with the Chicago skyline and Lake Michigan in the background, golden sky glow.

Two friends posing on the bow of a sailboat over turquoise ocean waters and blue sky — one in a yellow swimsuit, the other in a black top, denim skirt and captain’s hat, while a person photographs them from the deck.

Group of friends lounging on a colorful paddleboard and floating board in turquoise water with sailboats nearby, an American flag overhead and Chicago skyscrapers under a sunny blue sky.

Two women in sunglasses smiling on a boat on Lake Michigan, turquoise water, moored yachts and the Chicago skyline of skyscrapers under a blue sky.

Selfie on a sailboat with a smiling group in swimsuits on deck, Chicago flag and skyline visible over turquoise Lake Michigan waters.

Person in brown bikini standing on a sailboat deck holding the rigging, turquoise lake and urban skyline under a bright blue sky with fluffy clouds and a passing plane formation.

Cheerful group of women in swimsuits and captain hats lounging on the bow of a sailboat with sails up, flags flying and blue sea on the horizon.

Sailboat deck at night watching red fireworks burst over a busy harbor, bright bursts reflecting on rippling water and silhouetted passengers

Group of friends partying on a navy-hulled sailboat at an urban lakefront harbor, American flag flying, small inflatable dinghy alongside, people in swimsuits enjoying a sunny summer day

Friends laughing on a sailboat deck on Lake Michigan—one wearing a captain’s hat—while a fourth snaps a photo, with the Chicago skyline and cloudy sky in the background.

Blue-hulled sailboat with tall mast anchored among several yachts in clear turquoise coastal waters, groups of people on deck enjoying a sunny summer boating day

Group of smiling young adults in swimwear and captain hats crowded on a sailboat deck on a sunny day with turquoise coastal waters and other boats in the background

Boat party on a sailboat — friends celebrating a bachelorette, woman in a 'Bride' top dancing and another in a patterned swimsuit with a drink, boats on coastal waters under a partly cloudy sky.

Person wearing a white jacket with 'BRIDE' on the back enjoying a sunny boat ride on an urban harbor with sailboats and a city skyline in the distance

Man in blazer and sunglasses holding a champagne bottle on a sailboat, sparkling water and a city skyline in the background.

Group of friends in swimsuits wearing colorful birthday party hats and holding drinks, posing and smiling on a sailboat deck with a busy urban waterfront skyline and marina in the background on a sunny summer day.

Two friends posing on a sailboat deck with the Chicago skyline and multiple boats on Lake Michigan on a hazy summer day.

Three smiling adults in sunglasses sitting on a sailboat deck in calm blue ocean under a clear sky, flashing peace signs beside a wrapped bouquet of yellow roses and a cozy blanket.

Person in a bucket hat lounging on a sailboat deck at sunset, long hair trailing, with an orange-glow urban skyline reflected on calm water

Two smiling people on a sunny Chicago boat selfie — one wearing a captain’s hat and chain, the other in a white sailing shirt, with blue water and sky behind them.

Expansive Luxury BYOB Yacht Cruise with Private Captain

5 (12)
4hr

From $2,999/party

experience

Sailboat party with a group of people in swimwear waving and lounging under a clear blue sky in a busy coastal harbor, surrounded by other yachts and a tree-lined shoreline.

Smiling group of women relaxing on a sailboat with the Chicago skyline over Lake Michigan at sunset, holding drinks.

Eight friends in bikinis posing on a sailboat with the Chicago skyline and Lake Michigan in the background on a sunny summer day

Sailboat cockpit with teak benches and helm overlooking Chicago skyline at sunset; inset wood-paneled cabin and galley interior.

Friends in swimsuits enjoying a white sailboat on blue water with the Chicago skyline behind them on a sunny day.

Five women in sunglasses and summer outfits smiling on a sailboat deck in calm blue coastal waters with other sailboats on the horizon — bride-themed bachelorette outing.

White sailboat gliding on turquoise lakefront waters with the Chicago skyline of modern skyscrapers under an overcast sky

Two smiling women in heart-shaped sunglasses and summer swimwear posing on a boat with a waterfront city skyline in the background.

Group of friends lounging and cheering on a bright pink-and-blue inflatable in turquoise harbor waters, holding drinks with yachts and a distant urban skyline under a clear blue sky

Woman wearing a gold-lettered “Bride to Be” veil on a boat, holding a bottle above turquoise water with a tree-lined beach and city skyline in the background — summer bachelorette on an urban waterfront.

Luxury Sailboat with Private Captain: Navy Pier Marina, downtown Chicago

5 (14)
4hr

From $170/person, $1,299/party

experience

Tour boat cruising the turquoise Chicago River beneath the Columbus Drive bridge with downtown Chicago skyscrapers on a sunny day

Smiling bartender in a sun hat and sunglasses pouring tropical cocktails into plastic cups at a tiki-decor boat bar on turquoise waterfront

Thatched roof leisure boat on the Chicago River with people on deck and downtown skyscrapers under a bright blue sky

Thatched-roof tour boat cruising bright turquoise downtown riverfront under a city bridge, passengers relaxing on the open-air deck by sunlit high-rise buildings

Group of friends in colorful leis, swimsuits and hula skirts enjoying a sunny boat party on the water with an urban skyline and waterfront park in the background.

Tiki-style party boat docked at a downtown riverwalk with passengers on the upper deck, tall office buildings and leafy trees along the waterfront, and a bright yellow life ring station visible.

Tiki-roofed double-decker party boat cruising calm coastal waters with an American flag and sailboats on the horizon under a pale evening sky

Tiki-style yellow party boat cruising a turquoise downtown river, passing under a bridge with people on deck and tall skyscrapers against a sunny blue sky

White two-story river tour boat with a thatched tiki-style roof docked along an urban riverwalk, decorative floral hull artwork and city buildings in the background.

Huge Tiki Party Boat with Bar Package Included (Minimum of 40 Guests)

Instant Book

5 (10)
3hr

From $70/person

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