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experience

Chicago Fulton Market Donut & Pastry Party: West Loop Donuts & Cookies on Restaurant Row image 1

Smiling woman in a black beanie holding a plate of matcha waffles topped with sliced strawberries inside a trendy pastel pink and green cafe with neon sign, floral ceiling decor and potted plants.

Assorted colorful gourmet donuts—pink sprinkled ring, green iced novelty, maple bar topped with crispy bacon, chocolate swirl bar, and sugar-coated cream-filled stick—arranged on newspaper-lined parchment.

Person at a café table enjoying a green matcha bubble waffle topped with sliced strawberries, chocolate bubble waffle in foreground, pink rose in a vase and layered matcha drink with ribbon on a marble table.

Colorful gourmet donuts with chocolate, icing, sprinkles and novelty toppings displayed on a pink rotating glass case in a bakery.

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Close-up of a strawberry-topped bubble waffle on a pink scalloped plate with a green matcha drink, small vase with a pink rose, and a cozy cafe background

Colorful assorted gourmet donuts on a pink rotating glass display case at a trendy indoor donut shop counter

Bright pink donut shop interior with a glass display of colorful donuts, a sparkling crystal chandelier, and a playful skull-shaped donut mural by large front windows

Smiling person in a beanie inside a wood-paneled cafe holding a plate of strawberry-topped waffles and speaking into a retro phone beneath a pink neon "Spill the Tea" sign.

Chocolate bubble waffle topped with sliced strawberries and blueberries on a scalloped pink plate, paired with a green matcha-style drink garnished with dried rose petals and a pastel ribbon, with a green bubble waffle on a pink plate in the background.

Pretty cafe brunch scene: pink plates with bubble waffles topped with sliced strawberries and berries on a marble table, paired with a layered matcha drink in a ribbon-tied jar and a pink rose

Chicago Fulton Market Donut & Pastry Party: West Loop Donuts & Cookies on Restaurant Row

Instant Book

4.9 (15)
2hr

From $65/person

Hotel

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Sleek city apartment open-plan kitchen with glossy deep-blue cabinets, marble waterfall island and wood breakfast bar, two black stools, pendant lights, potted plants, and floor-to-ceiling windows opening to an outdoor patio.

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Bright modern yoga studio with floor-to-ceiling windows, blue accent wall and woven wall art; three blue mats with rolled towels on light wood floor, mirrored wall and TV showing a yoga pose.

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Modern sunlit atrium lounge in an urban high-rise with floor-to-ceiling glass, hanging filament pendant lights, white wicker chairs and tables, and abundant potted tropical plants with a vertical green wall.

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Bright spa-like modern bathroom with a frameless glass walk-in shower, wood vanity with white countertop and sink under a large mirror, towel rack and toilet.

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Luxury High-Rise Apartments at Sentral Michigan Avenue

From $129/night

experience

Bachelorette party on a sunny patio: bride in a white bikini and "BRIDE" cap flexes between two muscular shirtless men wearing red firefighter hats, red suspenders and black aprons, colorful balloon arch and party banner in background.

Valentine's Day studio portrait of a shirtless tattooed male model flanked by red heart-shaped balloons (one covering his waist) and a red 'Be my Valentine' teddy bear on a gray backdrop.

Backyard pool party scene: shirtless man lifts a woman in a bikini while pouring a drink from a can into her open mouth under a sunshade, colorful inflatables floating in the pool.

Group of adults in colorful swimsuits posing playfully and kissing at a nighttime waterfront backyard pool party under string lights

Three people pose in a sunny tropical backyard: two muscular men in orange safety vests and red bow ties lift a smiling woman in a white bikini, bucket hat and heart-shaped sunglasses, framed by palm leaves and a pink mosaic border.

Playful scene: woman in satin pajamas leaning over a shirtless, bearded man laughing as he reclines on a green sofa in an apartment living room, paper plate and cup nearby.

Poolside scene in a tropical backyard: two shirtless men in swim briefs pour a drink into a laughing woman wearing a white bikini and sunglasses beside a blue swimming pool.

Indoor living-room party scene: shirtless man with a lion back tattoo pours a drink into a woman’s mouth as she leans back in a chair, surrounded by gold star garlands, a mantel with books and a TV, and a gold balloon.

Tropical-themed bachelorette party indoor photo: group of women in matching tees pose playfully with a muscular shirtless man in blue swim trunks in front of a colorful balloon arch and a “Bachelorette weekend” backdrop.

Sunlit shirtless man lounging poolside on stone steps, arms behind head showing toned abs and muscular torso with turquoise pool tiles in the background.

Three people at a waterfront pool: two muscular men in black swim briefs lift a woman in a white swimsuit and sunhat who holds a large pink heart float, with canal-front homes and blue sky behind.

Sunny pool party by palm trees: woman in white bikini perched on shoulders of two shirtless men flexing, another shirtless man kneeling wearing a Hot Mess sash holding two face cutouts beside a modern resort pool.

Smiling group of friends in swimsuits at a summer poolside patio party — two shirtless men with red bow ties flexing in front, women in bikinis and sunglasses.

Lively group photo of a dozen friends at an indoor living-room party — mostly women gathered around a shirtless man, hands joined in a cheer, pink heart sunglasses and cash on the floor.

Smiling group of friends in swimsuits taking a selfie in a bright beach-house kitchen, gathered around a countertop with drinks, sunglasses and a champagne bottle — sunny vacation vibe.

Playful couple on a white outdoor sofa in a tropical backyard lounge — shirtless tattooed man in swim brief leaning toward a smiling woman with a messy bun.

Sunny backyard poolside party with a smiling woman in a pink smiley-face bucket hat and two men wearing red toy firefighter helmets and red suspenders leaning at a decorated outdoor bar with drinks, towels, and palm trees in the background.

Lively tropical pool party with a group in swimsuits posing by a backyard pool surrounded by palm trees, an inflatable champagne bottle, fun face props and sunny blue sky.

Playful bachelorette party group photo in front of a pink rose wall — bride in a veil and heart-shaped sunglasses posing with smiling friends, two shirtless men and guests in colorful swimwear.

Tattooed man in minimal swimwear standing on a wooden pool edge above a woman in a white bikini sitting at a backyard pool, man holding a drink and pointing skyward, green shrubs and apartment building in the background

Chicago Male Strippers & Exotic Dancers for Bachelorette Parties, Girls’ Weekends & Birthdays

5 (10)
45min

From $225/party

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

experience

Person cooking at an outdoor hibachi-style grill with dramatic orange flames, squeeze bottles of sauces and a propane tank on a wooden backyard patio surrounded by trees.

Smiling selfie at a sunny backyard deck party with a group of friends seated at a long decorated table, raising pink cocktails above plates of food on an outdoor patio.

Group of friends posing at an indoor 30th birthday party with green balloon garland, gold "Happy Birthday" letter balloons and large gold "30" foil balloons, green fringe backdrop and festive beads.

Mouthwatering surf-and-turf plate with grilled shrimp, cubed steak and chicken, a scoop of fried rice, and stir-fried broccoli, carrots and onions on a white plate.

Colorful restaurant-style beef stir-fry: savory bite-sized beef in brown sauce, a mound of brown rice, and steamed mixed vegetables (broccoli, carrots, bell pepper, onion) on a white plate

Close-up of shrimp stir-fry with glazed shrimp, broccoli, zucchini, mushrooms and carrot slices served with brown rice on a white plate

Glazed grilled chicken with fried rice and vibrant stir-fried broccoli, carrots, and onions served on a white plate.

Pan-seared sea scallops in a glossy savory sauce with broccoli, carrots and onions, served with fried rice on a white plate — Asian-inspired seafood entree.

Eight women wearing celebratory sashes seated at backyard patio tables for a bachelorette-style brunch, smiling with drinks and salads in front of a striped ‘Saddlin’ Up’ banner and wooden fence in late-afternoon sun.

Group of people in colorful costumes — including a referee, a wizard with a long grey beard, cowboy hats and an American-flag suit — posing inside a wood‑paneled mountain cabin with large windows looking out to pine trees.

Group of friends laughing and waving around a long outdoor dinner table on a wooden cabin deck in a pine forest, with a flaming griddle in the foreground and bowls, bottles and condiments on the table.

Two people smiling in a party photo in front of a shiny green sequin backdrop with a gold, white and green balloon arch — woman giving a thumbs up at an indoor celebration.

Smiling group at a backyard poolside gathering holding a black promotional banner on a concrete patio, surrounded by succulents, stairs and hillside landscaping.

Group of friends posing and flashing peace signs at an evening backyard patio dinner party with white-covered chairs, lit house wall and a palm tree silhouette

Two people smiling on a sunny backyard patio birthday celebration — one wearing a pink sash and tall novelty hat — griddle with rice and condiment bottles in the foreground.

Magician entertainer performing a flaming-hat trick at an outdoor kids' party — smiling children gathered close with colorful props and excited faces.

Five people posing playfully at an outdoor Asian-inspired photo booth with red drapery and paper lanterns — two men in blue uniforms, a woman in a black slit dress holding a red fan, and two women in colorful dresses smiling.

Group of adults posing at a backyard party in front of a red-and-black draped backdrop with paper lanterns, wearing bright floral kimonos and patterned dresses, smiling and striking playful poses.

Festive backyard celebration under a white canopy with long black-and-pink tables, floral centerpieces, pink fans, glassware and plated salads on the lawn.

Sunny suburban backyard party with a long table under a black canopy decorated with red paper lanterns and place settings, a flat-top grill in the foreground and a smiling cook in a large straw hat posing beside it.

Group photo at an outdoor Asian lantern–themed backdrop with red drapes: two men in blue shirts and caps giving thumbs-up and two women in black and floral dresses posing playfully.

Festive outdoor patio birthday backdrop with red, black and gold drapes, a 'Happy Birthday' banner featuring red paper lanterns and flame graphics, and hanging decorative lanterns.

Family birthday dinner party in a home dining room — long table with red and black linens, cherry blossom garlands and lantern centerpieces, plates of food and smiling guests posing together.

Playful backyard selfie at dusk — smiling person wearing a tall black hat with Japanese characters and a red circle, friend leaning in and sticking out their tongue.

Smiling hibachi chef and four friends holding flaming torches by an outdoor griddle under warm string lights at night

Private Hibachi Chef at Home: Dinner, Fire Show & Fun in Chicago

5 (30)
2hr

From $60/person, $600/party

experience

Friends clinking glasses—beers, cocktails and pizza—at a colorful, trendy bar with disco balls, neon lights and a lively celebration atmosphere

Vibrant brunch spread on a wooden table: pancakes with bacon and strawberries, glazed donuts, crispy bacon strips, fries, mixed green salad, fried chicken bites, pizza, quesadilla and colorful cocktails.

Five women laughing and cheering around a shuffleboard table in a cozy indoor bar, holding cocktails and wine beneath vintage framed photos.

Vibrant brunch spread on a colorful table: glazed donuts and mini pancakes with berries, pizza, fries, fried chicken bites, salads, deviled eggs, crispy bacon, cocktails and mimosas with hands reaching in.

Four women laughing and reacting around a shuffleboard table at an indoor game bar, drinks on the counter, globe pendant lights and exposed ducts in a lively urban nightlife setting.

Two friends toast espresso martinis under a blue-and-pink neon record sign on a brick wall lined with vintage music posters in a trendy neon-lit bar.

Boozy Weekend Brunch with Shuffleboard Games in Chicago

5 (20)
1hr 30min

From $50/person

experience

Home cook in a modern marble kitchen pouring olive oil from a glass bottle over chopped herbs in a plastic container on a cutting board, with a stove and colorful glass bottles on a shelf in the background.

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Group of friends in a cozy home kitchen gathered around a stove and island with multiple plated pancakes; a chef wearing a glove gives a thumbs-up under hanging pendant lights while others smile, with bottles and a TV showing sports in the background.

Fine-dining plated entrée: seared chicken on pearl couscous and green pea purée, topped with blistered shishito peppers and roasted squash on a white rimmed plate, several identical plates blurred in the background.

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Smiling home cook in a bright modern white kitchen stirring brown sauce from a plastic tub, with a bowl of leafy lettuce, pasta salad, jar of pickles and utensils on the counter during meal prep.

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Private Chef Dinner Experience in Chicago (Home or Rental)

5 (34)
2hr

From $65/person

experience

Five women laughing and cheering around a shuffleboard table in a cozy indoor bar, holding cocktails and wine beneath vintage framed photos.

Four women laughing and reacting around a shuffleboard table at an indoor game bar, drinks on the counter, globe pendant lights and exposed ducts in a lively urban nightlife setting.

Group photo of smiling women posing together inside a dimly lit restaurant or bar, casual summer outfits, denim and a cowboy hat

Six friends in summer outfits smiling and posing inside a cozy café under warm pendant lighting and window blinds.

Six espresso martinis stacked like a cocktail tower on a wooden bar counter, creamy foam and warm golden bokeh lights in a cozy bar interior

Top-down view of a casual pizzeria spread with pepperoni, margherita and arugula pizzas, fries and sweet potato fries, buffalo wings, avocado salad, and orange cocktails on a colorful table.

Bachelorette Party Shuffleboard Night at Electric Shuffle, Chicago

5 (20)
1hr 30min

From $20/person

experience

Chicago Happy Hour: Shuffleboard, Cocktails & Pizza Specials image 1

Colorful drinks lined up on a bar counter: a bright blue plastic cup, two salt-rimmed citrus cocktails, a sparkling water bottle, an orange aperitif in a wine glass with an orange slice, and a pint of beer against warm, backlit liquor shelves.

Retro blue happy hour poster reading "HAPPY HOUR" — Mon-Fri 3-5PM with $5 beers, house wine, seltzers, High Noons & fries and $10 espresso martinis, margaritas, ranch waters & house pizzas; grayscale hand holding a cocktail coupe.

Two friends toast espresso martinis under a blue-and-pink neon record sign on a brick wall lined with vintage music posters in a trendy neon-lit bar.

Group of friends at a lively indoor bar playing shuffleboard, cheering and reacting to a shot beneath hanging globe lights with colorful drinks on the counter — upbeat nightlife scene.

Two espresso martini cocktails clinking in coupe glasses in a cozy home-bar setting with wooden shelves, potted plants and vintage audio gear

Flat-lay of a colorful casual dining spread with pizza, sliders, chicken wings, sweet potato fries, fries, quesadillas, veggie-and-pita dip platter, chips, dipping sauces and frozen cocktails on a wooden table

Friends clinking glasses—beers, cocktails and pizza—at a colorful, trendy bar with disco balls, neon lights and a lively celebration atmosphere

Group of five friends smiling and holding cocktails at a lively bar with globe pendant lights, pink marquee mirror lights and colorful nightlife ambiance

Chicago Happy Hour: Shuffleboard, Cocktails & Pizza Specials

5 (20)
1hr

From $5/person

experience

Lively bar/restaurant birthday party with staff carrying a sprinkle-covered cake topped with lit sparklers while a cheering crowd holds a banner under warm pendant lights

Group of friends at a lively indoor bar playing shuffleboard, cheering and reacting to a shot beneath hanging globe lights with colorful drinks on the counter — upbeat nightlife scene.

Group of five friends smiling and holding cocktails at a lively bar with globe pendant lights, pink marquee mirror lights and colorful nightlife ambiance

Bartender handing a tray of bright red and blue cocktail shots to cheering guests in a lively indoor bar party with people taking photos

Two women leaning over a long shuffleboard table in a neon-lit urban bar with purple hanging lanterns, a wall-mounted TV, round stools, and colorful cocktails on the counter.

Birthday Shuffleboard Party at Electric Shuffle Chicago

5 (20)
1hr 30min

From $20/person

experience

Chicago River Kayak Tour: Guided Architecture Paddle image 1

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Green kayaks lined on a dock along the Chicago River with people boarding, a tree‑shaded riverwalk and downtown high‑rise skyline with sunlight reflecting on the water.

Two paddlers in a bright green kayak on the Chicago River, passing beneath a flag-lined downtown bridge with the sunlit Chicago skyline of glass skyscrapers.

Chicago River Kayak Tour: Guided Architecture Paddle

5 (15)
2hr

From $55/person

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