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experience

Two joyful women at a bachelorette celebration on a sunny spring downtown sidewalk — bride-to-be wearing a "Bride" sash and friend flashing a peace sign while holding a blue Chewbies pouch.

Vibrant close-up of sugar-coated strawberry gummy cubes spilling from a bright pink strawberry gummy pouch onto a yellow tabletop — colorful candy product shot.

Two laughing friends pose in front of a glowing vintage fortune-telling arcade machine with a turbaned automaton inside; one shows an engagement ring and wears denim shorts with a red packet in her back pocket.

Flatlay of bright yellow packets of citrus THC gummies with scattered orange sugar-coated gummy squares on a black-and-white checkerboard case over an orange background

Bachelorette gift box flatlay with teal and white Bride sashes, bridal veil, spa face masks, lavender sachet, colorful stickers and a pink bachelorette dare card for wedding prep

Smiling bride-to-be in veil and gold-lettered "Bride" sash playfully holding a raspberry near her mouth against a green backdrop

Peach-flavored sativa Delta-9 THC gummy pouches with sugar-coated orange rectangular gummies arranged on a red-and-yellow grid background

Pink stand-up pouch of strawberry-flavored indica Delta-9 THC gummies with sugar-coated red gummy strips on a pink-and-red checkerboard backdrop

Studio product shot: bright green-and-pink resealable pouch of Watermelon Gelato THC gummies with a bowl icon, flanked by two blurred matching bags on a pastel background

Bachelorette flat lay: pink tulle bridal veil with gold “The Bride” script and diamond icon, colorful sugar-coated gummy candies, a ring and a green candy pouch

Laughing friends at a bachelorette celebration against a pink stucco wall — a veiled woman tilts back as her friend playfully feeds her a red gummy from a teal snack pouch.

Chewbies FREE Bachelorette Gummies Party Box: Keep the Hangovers Away

4hr

From $0/person, $0/party

experience

Ink & Drinks: A Colorful Cocktail Art Night image 1

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Group art workshop in a bright industrial loft studio — long plastic-covered tables with people painting and working with inks, bottles, paper towels and cups beneath exposed wooden beams and large windows.

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Ink & Drinks: A Colorful Cocktail Art Night

5 (12)
2hr

From $145/person

Rental

The Jackpot - Sleeps 14, Hot Tub, Cinema, Fire Pit, Game Room, Bar image 1

Cozy suburban backyard hot tub at dusk under a pergola with twinkling string lights, steaming water, a fire pit and Adirondack chairs, and a hand holding a glass of red wine.

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Cozy modern bedroom with white linens, velvet green pillows and a patterned throw pillow on a bed against a navy accent wall, framed artwork above, a window with a pink sunset view and a small round bedside lamp.

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The Jackpot - Sleeps 14, Hot Tub, Cinema, Fire Pit, Game Room, Bar

5 (13)
Sleeps 14

From $620/night

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

experience

Pearl Party Boat Event Charter image 1

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Romantic candlelit dinner on a yacht—couple toasting champagne while a violinist plays, with a glowing waterfront city skyline at sunset.

Two-level floating lounge party boat on turquoise Lake Michigan waters with covered upper deck and the Chicago skyline in the background

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Pearl Party Boat Event Charter

3hr

From $2,400/party

experience

Group Kayaking Adventure: Scenic River & Lakefront Paddle Tours image 1

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Group Kayaking Adventure: Scenic River & Lakefront Paddle Tours

1hr

From $35/person

bar

Pete's Dueling Piano Bar - Chicago image 1

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Happy woman at a neon-lit bar holding a glass of ice, smiling across a busy bartop with cups, bottles and cocktail tools — casual nightlife scene.

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Pete's Dueling Piano Bar - Chicago

Club

$$

experience

Girls Night Out: Private Shopping Experience West Loop Chicago image 1

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Friendly sales associate chatting with a customer in a boutique jewelry and clothing shop, accessories on display and clothing racks in the background.

Three women in a boutique hands-on styling a beige trench coat — close-up of hands adjusting sleeve and belt, smiling stylist and jewelry details.

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Customer in a black mini dress and chunky platform boots browsing a brown satin dress and white blouse on a circular rack inside a boutique fitting room.

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Festive birthday snack spread on a wooden board: sprinkled glazed donuts with lit candles, bowl of fresh raspberries, crackers and cheddar slices; plate of croissants and green grapes with a bottle of rosé in a marble cooler in the background.

Smiling guest holding a small cup beside a birthday dessert spread with cupcakes, cookies and wine on a table inside a clothing boutique near fitting-room curtains and clothing racks.

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Birthday party table with a charcuterie board of cheese wedges, crackers, grapes and olives, stacked plates with gold forks, a pink instant camera, and a framed 'June' birthday sign.

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Two smiling women in a boutique fitting room trying on outfits — one in a beige faux-fur coat and white boots, the other in a black top and leggings.

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Shiny pink balloons floating over a party-ready spread of donuts, pastries, charcuterie, orange juice and wine set inside a boutique fitting room with curtained stalls and a hanging dress.

Girls Night Out: Private Shopping Experience West Loop Chicago

3 Reviews
2hr

From $250/party

restaurant

Cheering football fans at a lively pub watch party, many wearing England shirts and raising arms over a bar with pints, bottles and glasses

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Pub crowd of football fans cheering and clapping with raised arms, wearing England shirts, bottles and glasses on the table, watching a match on TV screens in a cozy bar

Lively sports bar crowd cheering with fists raised as fans in England shirts watch a soccer match on wall TVs, pints and glasses on the bar in a packed pub.

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The Albion Manor: Your Patio and Soccer Destination

American

$$$

bar

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AJ Hudson's Public House: Soccer Bar with Covered Patio

Sports

$

experience

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Private Party Experience at CuddlePups

1hr

From $34/person, $500/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

Four smiling women in sparkly cocktail dresses wearing bridal sashes and holding cocktails on a rooftop at night, city skyline and string lights in the background — bachelorette party celebration.

Custom Party Sashes - Bachelorette, Birthday & Girls Night

10min

From $5/person

experience

Private Charters for Day Parties & Fireworks Cruises image 1

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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

experience

Luxury party van interior with red LED ambient lighting, diamond-quilted leather seats, illuminated side table and cup holders, and a starry fiber-optic ceiling.

Sleek black Mercedes Sprinter high‑roof van parked on a downtown street, glossy side reflecting red brick buildings and bare trees on an overcast day.

Luxurious party van interior at night with red quilted leather seats, vibrant blue LED accent lighting, built-in screen showing an aerial performer, cupholders and city buildings visible outside.

Vibrant luxury shuttle van interior at night with red quilted leather seats, blue and red LED neon accents, illuminated side table and cup holders, and an open sliding door.

Luxury shuttle interior with red quilted leather seats, glossy black fold-down table with four cup holders and red LED accent lighting, window revealing parked cars on a city street outside

Red-lit luxury passenger van interior with quilted red-and-black leather bench seats, starry ceiling lights and a glowing neon sign reading "You Deserve Luxury".

Luxury black shuttle van parked on a downtown city street with sliding door open, revealing red-and-black quilted leather seats, cup holders, a small table, and brick buildings in the background

Two hands clinking champagne flutes beneath a red neon sign reading "You Deserve Luxury" in a dim, neon-lit lounge

Luxury Sprinter Van Rental - Seats 8-10: Perfect for Events & Trips

3hr

From $450/party

restaurant

The Dandy Crown's Secret Garden Pop-Up image 1

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The Dandy Crown's Secret Garden Pop-Up

American

$$$

experience

Vibrant spread of premixed craft cocktail bottles and mixed drinks on a tabletop, garnished with lime, cherries and pineapple, surrounded by barware, jigger, olives and nuts against a wood backdrop.

Sunlit stone tabletop with two bottles of amber craft cocktails, a tall tiki-style drink garnished with pineapple and cherry, and a jalapeño-rimmed margarita, surrounded by limes and sliced jalapeños.

Copper tabletop home bar scene with two bottles of craft cocktails, an espresso martini coupe, a crystal old-fashioned with cherry and orange peel, gold shaker and bar tools, and a handful of pistachios.

Sunny poolside scene with two bottled cocktails and matching margarita glasses — pineapple-chili rim and salted lime wedge on a stone deck.

Four colorful cocktails being poured on an outdoor patio bar—pink martini with a lime twist, salted-rim margarita garnished with a lime wheel, amber old-fashioned with an orange peel, and a pineapple-cherry tropical glass.

Bottle of espresso martini cocktail with a crema‑topped martini glass, gold cocktail shaker, jigger and spring strainer arranged on a shimmering gold tabletop with a golden curtain backdrop.

Bar Strength bottled cocktails, real juices, real ingredients

1hr

From $22/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

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!

5 Reviews
3hr

From $1,630/party

experience

Chicago Yacht Party Charter, Birthdays & Bach Parties image 1

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

Customized Yoga at the Beach or brought to YOU! BYOB and Add Ons Available. image 1

Dog-friendly yoga class inside an urban brick-walled studio, participants on mats stretching and raising arms while small dogs lounge nearby under track lighting and tall windows.

Customized Yoga at the Beach or brought to YOU! BYOB and Add Ons Available. image 4

Group yoga class on mats in a school gymnasium, participants raising arms toward a large wolf mascot mural above basketball hoops on the hardwood court.

Group yoga/stretch class in a cozy loft-style studio with exposed brick walls, herringbone wood floor, twinkling string lights, large windows overlooking a downtown street, chalkboard wall and participants on mats doing side stretches.

Group yoga class in an indoor studio: students on mats in child's pose with blocks, water bottles, and a mirrored wall

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Customized Yoga at the Beach or brought to YOU! BYOB and Add Ons Available. image 10

Rooftop yoga class with seven people in colorful activewear holding tree pose on mats on a sunny urban rooftop, modern glass office buildings forming a downtown skyline behind them.

Customized Yoga at the Beach or brought to YOU! BYOB and Add Ons Available.

3 Reviews
1hr

From $20/person, $180/party

bar

Smiling friends enjoying outdoor patio dining and happy hour—sharing cocktails and small plates like bruschetta, fries and salads on a wooden table under string lights.

Green ceramic tiki mug with red leaf garland, pink cocktail umbrella and straw on an outdoor patio railing, fern leaves nearby and warm bokeh string lights in the evening background

Group of friends toasting colorful cocktails over a wooden table of shareable summer dishes on a lit outdoor patio — al fresco dining with string lights.

Close-up of two hard seltzer cans—black cherry and orange vodka seltzer—clinked together and held by hands with long manicured nails at a lively social gathering.

Overhead view of a bustling indoor sports bar at night — long central bar with bartenders, crowded tables and booths, patrons watching multiple large TV screens showing games.

Overhead of a bright, party-ready vegetable crudité platter — cherry tomatoes on the vine, purple cauliflower, radishes, multicolor carrots, cucumbers, mini bell peppers, asparagus and romaine, served with three dips and seeded crackers on a dark wood table.

Three hands toasting: a pint of beer, a lime-rimmed cocktail with chili salt, and a pink grapefruit spritz in a wine glass beneath warm string lights on a rooftop patio.

Hand holding a vibrant orange cocktail in a textured glass with ice and a green leaf garnish at a dim, stylish bar with a blurred background.

Golden battered fish and chips on parchment with thick-cut fries, five dipping sauces, and a hazy craft beer garnished with an orange wedge on a wooden patio table

Overhead view of square-cut pepperoni, cheese, and sausage pizzas on wooden paddles on a dark table; a hand reaches for a slice beside a glass of beer and a small plate of colorful veggies and dipping sauce.

Top-down view of a Caesar-style romaine salad in a bowl, topped with shredded Parmesan and crunchy golden breadcrumbs on a dark wooden table.

Pink grapefruit cocktail in a tall glass with ice and a grapefruit wedge, set on an outdoor patio railing with fern leaves and warm bokeh string lights in the background.

Three colorful iced cocktails on an outdoor patio table at dusk — grapefruit-topped pink wine cocktail, tall purple-pink highball with lemon and blueberries, and an orange rocks glass garnished with basil, string lights bokeh in background.

Modern urban restaurant interior with tan leather banquettes, high-top tables and stools, mirrored wall, hanging ferns, warm pendant lights and hardwood floors.

Cozy downtown urban rooftop patio at dusk, warm bistro string lights draped across a metal pergola over a multi-level outdoor dining area with blurred city skyline in the background.

Hand holding a clear purse-shaped glass pitcher of iced orange cocktail garnished with three orange slices on a sunlit outdoor patio — refreshing summer drink close-up.

Lively downtown bar interior at night — overhead view of a crowded space with groups at a long counter and booth tables, bartenders pouring drinks, TVs showing sports, hanging industrial lights, and blue beer buckets on tables.

Two smiling young men posing together in a lively bar, one flashing a peace sign while holding a phone and the other holding a drink; casual clothes with visible 'Ann Arbor' and 'M' logos, bar stools, TVs and warm ambient lighting in the background.

Benchmark: Fun Vibes, Delicious Bites & Rooftop Views

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bar

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Overhead view of a vibrant southwestern salad on a white plate with sliced avocado, cherry tomatoes, shredded tortilla strips, cilantro, grilled chicken and creamy dressing.

Kirkwood: Sports Bar with a Massive Beer Garden

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