House in Chicago, IL
14 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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
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
Amenities at The Jackpot - Hot Tub, Cinema, Game Room, Fire Pit, Bar, Garage - Sleeps 14
Non-smoking
No pets allowed
Family friendly
Map of Chicago, IL
Ratings and reviews
10 / 10Outstanding·Feb 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.
10 / 10Outstanding·Dec 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
10 / 10Outstanding·Nov 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.
$$$$
Top rated by guests
10Outstanding
(6 Ratings)
"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. "
Rob M.Don't miss out! Price and availability may change
