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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

The Lucky Penny: Lincoln Park 3-Story Townhome & Rooftop Oasis image 1

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

5 (10)
Sleeps 10

From $590/night

Hotel

Staypineapple: Iconic Boutique Hotel in The Loop image 1

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Staypineapple: Iconic Boutique Hotel in The Loop

4.9 (13)

From $139/night

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