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

Chicago, Illinois
$1517 avg/night Minimum Stay 2 Nights
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 14

Max Sleeps

Night 2 nights

Min Stay

Welcome to The Jackpot — a one-of-a-kind luxury home in Chicago designed for groups who want more than just a place to sleep. This is where your crew gathers, celebrates, and makes the kind of memories you'll be talking about for years.

WHY GROUPS CHOOSE THE JACKPOT

This isn't your typical rental — it's a 3-level luxury home built for togetherness. Whether you're celebrating a milestone, hosting a weekend reunion, or just getting your favorite people under one roof, every corner of this house was designed for your group to connect.

Ask us about special rates for celebrations, retreats, and photo shoots!

THE BACKYARD — Your Private All-Season Oasis

Step outside to your personal resort. The backyard is a showstopper year-round.

✦ Premium 5-person hot tub with fountain jets & LED lights
✦ Louvered pergola — opens for sun, closes for rain/snow, with privacy curtains
✦ Cozy fire pit surrounded by wooden chairs
✦ Propane BBQ grill for group cookouts
✦ Ambient string lights & walkway lights for the perfect evening

ENTERTAINMENT — Two Dedicated Fun Zones

You will not be bored here. The lower level has two spaces built for group fun.

The Game Room & Bar:
✦ Ping pong & foosball tables
✦ Custom bar stocked with essentials
✦ Record player with vinyl collection
✦ Poker set & board games

The 4K Cinema:

✦ 120 projector screen — the biggest screen you've ever watched a movie on
✦ 4K projector with all streaming apps pre-installed
✦ Immersive AI Dolby surround sound
✦ Two ultra-comfy memory foam couches & oversized bean bags
✦ The perfect spot for movie nights, game day watch parties, or winding down after a night out

THE SUN ROOM — Your Morning Oasis

Wake up slow. This light-filled room is where your group gathers for coffee, conversation, and planning the day ahead.

✦ Large wicker sectional with thick cushions
✦ Dining table & bench seating
✦ Privacy curtains for a cozy feel

KITCHEN & COFFEE BAR

A fully stocked kitchen ready for everything from morning lattes to late-night snacks.

✦ Full coffee & tea bar: Nespresso, milk frother, flavor pumps, premium coffee & precise electric kettle
✦ High-end appliances: Large Ninja air fryer & more
✦ Fridge with filtered water & ice dispenser
✦ Fully stocked: All essential cookware, bakeware, dishes & utensils

SLEEPING — 14 Guests Across 5 Bedrooms + Cinema Room

Every bedroom has real beds. The cinema room doubles as a crash-ready lounge with two full-sized memory foam sleeper sofas.

Top Floor (3 private bedrooms):
✦ Bedroom 1: King bed
✦ Bedroom 2: Queen bed
✦ Bedroom 3: Full-sized bunk bed

Main Floor:
✦ Bedroom 4: Queen bed

Lower Level:
✦ Bedroom 5: Two twin-over-twin bunk beds
✦ Cinema Room: Two full-sized memory foam sleeper sofas

3 full bathrooms (one on each level) with fresh towels, hair dryers & starter toiletries.

THE PERFECT CHICAGO HOME BASE

The Jackpot sits in a quiet, tree-lined North Side neighborhood — peaceful enough to enjoy your backyard hot tub at midnight, connected enough to reach everything Chicago has to offer.

Getting Around:
✦ Blue Line (9-min walk) — your direct line to downtown & O'Hare
✦ I-90: 4-min drive
✦ O'Hare Airport: 13-min drive
✦ Downtown / The Loop: 16-min drive

Neighborhood Vibes:
✦ Lincoln Square (8 min): Charming shops, restaurants & European bakeries
✦ Logan Square (10 min): Breweries, brunch spots & craft cocktails
✦ Wicker Park / Bucktown (15 min): Boutiques & vibrant nightlife
✦ Wrigleyville (15 min): Bars, rooftops & game-day energy

Attractions & Venues:
✦ Wrigley Field: 15-min drive
✦ Millennium Park / The Bean: 17-min drive
✦ United Center: 17-min drive
✦ Museum Campus (Shedd / Field): 20-min drive
✦ McCormick Place: 24-min drive

Your Group, Your Way:

✦ Want a quiet night in Hot tub → fire pit → movie night in the theater
✦ Want to go out You're 15 minutes from River North, Wrigleyville, and Logan Square
✦ Need recommendations Message us — we've got the best local picks

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Locally-owned & Organized Tours & Activities
  • KITCHEN

    Coffee/tea Maker Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Barbecue Grill Garden Patio
  • POOL/SPA

    Hot Tub
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Bidet Hair Dryer Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • THINGS TO DO

    Fitness Center
  • ENTERTAINMENT

    Arcade/game Room Books Foosball Table Games Stereo Table Tennis Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Rates & Availability

Review Review

  • Rob M.

    Submitted Feb 6, 2026

    Stayed Feb 3, 2026

    The house was very clean and comfortable. The kids loved the hot tub and the movie room. Also, the host was very attentive and available for any questions we had.

  • Wood F.

    Submitted Dec 24, 2025

    Stayed Dec 20, 2025

    Abe was very communicative and thoughtful on making sure we had everything we needed. Location was great for us with family in being able to visit with family in park ridge and spend time in the city. Great place to stay for multi families with or without kids

  • Margaret P.

    Submitted Nov 24, 2025

    Stayed Nov 21, 2025

    My family absolutely loved our stay at The Retreat! Tucked in the middle of a friendly Chicago neighborhood, it truly felt like we were in an urban oasis. The home is beautifully updated, with tons of space for a crowd. The kids loved the bunk beds, ping pong table and of course the hot tub. The adults spent a lot of time gathering in the spacious, well-appointed kitchen and enjoying the comfortable sitting area around the TV. The host Abe was super responsive to our needs and went well above and beyond, even securing a DVD player after we inquired. This is a unique find in Chicago's Albany Park neighborhood and a spot I'll rave about to anyone who will listen.

Your dates are Available!

Total

Includes taxes and fees
$1,517+
View details