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 Elgin

4 out of 5 average rating, 4 reviews

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

Pets Welcome w/ Fee | 2 Kitchens | Cookout Ready | Quiet 80 Acres This tranquil retreat offers rustic luxury with plenty of space to relax and reconnect. A spacious living and dining area makes it ideal for family gatherings. Set on a peaceful estate, the home features serene views of nature and horses. While it feels secluded, it’s just 36 miles from downtown Chicago, offering easy access to city amenities. You can even watch the Hoffman Estates fireworks from this 6-bedroom, 5-bath home!

Villa in South Shore

4.64 out of 5 average rating, 53 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

Villa in West Town

4.77 out of 5 average rating, 13 reviews

Chic ART-3BRHome360Roof+HotTub+CarGarage+12Guests

🎉 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!