Villa holiday rentals in Chicago

Find and book unique villas on Airbnb

Top-rated villa rentals in Chicago

Guests agree: These villas are highly rated for location, cleanliness and more.

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Villa in Wilmette

Luxury Chicago-Wilmette High End Private Residence

Our Property Is Best Described by Our Guests : 5/5 Amazing location and space to breathe We needed a long term place to stay, and wanted a place to LIVE. We needed a home and this was the perfect answer. Located in a beautiful safe neighborhood, literally minutes from the lake, from Old Orchard mall, grocery stores, and everything else we needed. Only a 5 minute drive to a park and ride for the train. Very quiet despite proximity to everything Perfect 10+ We will be back just ! Thank you!

Superhost

Villa in South Shore

4.65 out of 5 average rating, 55 reviews

Rooftop | Villa | Events

Gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Party Backyard/Rooftop Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: Three levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record.

Superhost

Private room in South Shore

Queen Suite/Terrace in Lakefront Rooftop home

Enjoy a Private terrace view of Chicago life. A minute walk from Tennis court, Golf Course, Beach, Play ground and Cultural Center. A short drive from museums, lake shore, downtown, UofC, restaurants & night life. Enjoy upper home, from your own private patio, to a breathtaking rooftop and relaxing garden. This is 5 ⭐️ w/ Private Bath, Personal fridge/microwave. Massage table, Jacuzzi/spa bath, foot baths, amazing views indoors and outdoors. Enjoy a rooftop party.

Superhost

Villa in West Town

4.81 out of 5 average rating, 16 reviews

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp

🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 ✅DM for YOUR SPECIAL RATE! 🎯 Free Private Garage 🎯 Hot Tub 🎯 360° Roof Deck with Skyline + Willis Tower Views Perfect for family trips, romantic escapes, or friend getaways! ✨ Private keyless entry 🛏 Luxury KING, 2 QUEEN beds + cozy fireplace 🍽 Full kitchen + balcony 📺 3 Smart TVs (Netflix, Disney+, Prime) 🚀 Super-fast WiFi Book now for your unforgettable Chicago stay!