you found something special
THE COURTYARDat dusk
One of the most loved homes on Airbnb, according to guests.
Reserved for homes with 9+/10 ratings and verified-guest satisfaction.
Perfect rating across 20 verified stays
— before we go further
The house is the same. The weekend isn’t. Tell us what you’re here for and we’ll point you at what matters.
The Jackpot sits in North Park, a tree-lined neighborhood ten minutes from everything and a world away from downtown noise. Three breweries within walking distance. Some of the best Mexican and Filipino food in the city around the corner. And a backyard that makes most groups cancel their dinner reservations.
Half Acre Beer Garden · Lula Cafe · Old Irving Brewing · Gene’s Rooftop Wine Garden — all within 10 minutes.
“If you are reading this review while searching for a rental property in Chicago, just stop immediately. THIS IS THE PLACE. Guaranteed.”
“Tucked in the middle of a friendly Chicago neighborhood, it truly felt like we were in an urban oasis. The kids loved the bunk beds, ping pong table and of course the hot tub. Abe was super responsive and went well above and beyond.”
“We had a bachelorette party for 13 guests. Everyone had a bed, a place to eat, and a place to sit around and relax. It was really well done.”
“The house was very clean and comfortable. The kids loved the hot tub and the movie room. The host was very attentive and available for any questions we had.”
“The kitchen was the perfect space for entertaining for a girl’s night! The outdoor hot tub and fire pit were a great bonus. Go ahead and save for your next girls trip to Chicago!”
“Clean, well-stocked, great amenities, inviting decor, accessible location. The host is organized, flexible, thoughtful and supportive.”
“Phenomenal space! It was perfect for my large group of 14!”
“This exceeded our expectations. The home was even nicer in person and the host was attentive every step of the way. It felt like we were staying at a 5-star hotel. We will definitely book again next time we are in Chicago.”
— the person behind the keys
I bought this house, designed it, and host it personally. Three years deep in the wedding and event venue world taught me what makes a weekend actually work — and I built The Jackpot to be that. No management company. No outsourced hospitality.
When you book directly, a few things happen that don’t happen on Airbnb:
Submit your dates above and I’ll be in touch personally.
