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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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The Jackpot - Sleeps 14, Hot Tub, Cinema, Fire Pit, Game Room, Bar image 22

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

Rental

Cozy retro living room with caramel leather sectional, vibrant patterned rug, white coffee table, electric fireplace, mid-century TV console and hanging disco ball beneath a colorful Chicago skyline mural.

Cozy retro lounge with brown leather sectional, colorful throw pillows, low white coffee table, glowing electric fireplace and a large Chicago skyline mural under warm, dotted ambient lighting

Cozy sunlit mid-century modern living room with wood ceiling, patterned area rug, fireplace, and vintage TV console displaying Netflix; bright entryway with wooden front door and retro wallpapered cubby.

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 4

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 5

Vibrant disco-inspired living room with green walls, olive velvet armchair, tufted leather daybed trimmed in blue string lights, colorful shag rug, potted plants, gold oval mirror with small disco balls, and framed 'To The Disco' art.

Cozy mid-century modern urban bungalow interior with a leather sofa and colorful pillows, wooden staircase against an exposed brick wall, green open kitchen cabinets, pendant lights and hanging plants.

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Cheery mid-century modern dining nook with green lower cabinets and marble countertop coffee station, striped wood accent wall with orange cocktail poster, velvet orange curtains, wooden ceiling and table, white chairs, and a vase of citrus branches by a large sunlit window

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Cozy mid-century style dining nook with wood ceiling and floors, green kitchenette and Aperol poster, long wooden table with white chairs, exposed brick wall and orange velvet curtains, and a colorful arcade machine by the window.

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Cozy coffee bar with marble countertop and green cabinets, wood‑slat accent wall and warm LED lighting, glass shelves of mugs and glasses, syrup pumps and drip and single‑serve coffee makers, Aperol Spritz poster.

Contemporary bathroom interior with glossy vertical red tiles, backlit oval mirror above a wood vanity, white toilet, ribbed glass shower door, and a playful tiger-striped bath rug.

Cozy pink boutique guest room with wooden bed, floral arched headboard, textured pillows and folded towels, opening into an en-suite bathroom with illuminated oval mirror, red tile, brass fixtures, two bar stools at a vanity and a tiger-print bath mat, warm ambient lighting.

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 22

Cozy boho guest room with twin beds, retro orange floral arch murals, textured pink and striped pillows, warm pendant light, LED-lit vanity with stools and exposed wooden beam ceiling

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 24

Sunlit boho-chic bedroom with retro orange-and-yellow floral arch headboard, textured pink bedspread and pillows, rolled white towels and a lighted vanity mirror with gold-framed stools.

Cozy modern bedroom with queen bed, teal throw and pillows, vertical wood-slat headboard, orange bedside lamp, open closet and round vanity mirror.

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Cozy mid-century modern bedroom interior with warm wood-plank ceiling, teal bed runner, rust and teal velvet pillows, patterned lumbar cushion, bedside lamp, and built-in vanity with round mirror.

Cozy modern urban bedroom with exposed wood-beamed ceiling, slatted wood accent wall, white quilted bed, teal and rust throw pillows, teal curtains over sliding balcony door, ladder desk and mid-century wooden dresser

Cozy bright bedroom with wooden vaulted ceiling and mid-century furniture — queen bed with white quilt and teal throw, teal curtains opening to a balcony with flower boxes, wall-mounted TV showing Netflix, full-length mirror and small desk.

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Bright modern bathroom with skylight and hanging plants, backlit mirror and globe pendant lights, glass shower with gold hardware, wood floating vanity, white toilet and warm beige tile

Cozy retro-styled living room with olive-green accent wall, velvet green armchair and matching daybed, colorful shag rug, round coffee table, tall oval mirror, tropical potted plant, disco-themed posters and string lights.

Colorful cozy living room with TV showing a streaming screen, green velvet armchair with rainbow cushion, bright floral shag rug, mid-century wood console, tufted daybed with patterned pillows, ceiling fan and potted plant

Cozy boho living room nook with olive-green walls, tufted leather-backed daybed layered with textured throws and rust-green pillows, pink LED strip lights, framed retro art, hanging plants, blue table lamp and colorful shag rug.

Cozy Chicago‑themed lounge nook with green sectional, tan leather back cushions, red and cream throw pillows, hanging plants, framed heart art and blue LED string lights.

Vibrant cozy living room corner with olive-green walls and pink accent, quilted green daybed with leather back cushions, coral and cream throw pillows, folded pink towels, hanging plants, framed art, purple LED strip lighting and disco-ball pendants.

Cozy colorful lounge with hot-pink cabinets and mini fridge, green accent wall, sectional daybed with throw pillows, framed art, hanging plant, LED strip lights and hardwood floor

Sunlit boho-chic living room with green accent wall and pink cabinet, a cozy daybed layered with textured green and red pillows and folded blankets, hanging plants, framed art, disco-ball ornaments and sheer curtains.

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 40

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 41

Overhead open-plan floor plan: cozy living room with leather sectional, patterned rug, fireplace and TV, adjoining kitchen, six-seat dining table, luxury coffee/snack bar, entry nook and staircase.

Top-down 2-bedroom apartment floor plan with hardwood floors: primary bedroom with two beds and glam bar, second bedroom with vanity, central bath, stacked washer/dryer, owner closet and stairway.

Top-down view of a top-floor apartment layout with rooftop patio — string-lit wood deck and grassy area with two pink loungers, cozy outdoor sofa, indoor lounge with colorful rug and TV, double and twin beds, dry bar with mini fridge, and a small bath.

Cozy modern coffee station interior with Aperol Spritz poster, marble countertop, espresso machines, syrup bottles, glass mugs on floating shelves, wood‑slat wall and rust-colored curtains.

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis

5 (10)
Sleeps 10

From $590/night

Hotel

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Staypineapple: Historic Boutique Hotel in Chicago's Loop

4.9 (13)

From $139/night

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