Luxury rentals in Cook County

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Top-rated luxury vacation rentals in Cook County

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Luxe

Condo in Chicago

5 out of 5 average rating, 9 reviews

Ultra Modern Luxury - New Construction 4 Bedrooms

🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, and vibrant dining, shopping, & nightlife. Featuring 4 bedrooms and 2.5 baths, the condo boasts a private rooftop deck with a fire pit 🔥, loungers, and patio seating. Just ½ block to the Red Line 🚇. Garage parking included. Concierge services available. Ideal for short-term stays, executives, or insurance clients. Enjoy comfort & convenience! ✨

Luxe

Apartment in Chicago

New place to stay

4BR Penthouse for 9 | Skyline & Sunsets

Temporary housing doesn't have to feel temporary. The Sol, a 4-bedroom penthouse on the 23rd floor in the Chicago Loop, 2,643 sqft of warm, bold, timeless interiors with west-facing views over the city skyline and sunsets. Sleeps 9 across 2 King suites and 2 Queen rooms, with three full bathrooms and a half bath. A real home in a real building, with the same doorman and neighbors as the residents who live here year-round.

Luxe

Apartment in Chicago

4.67 out of 5 average rating, 3 reviews

Spacious 3BR 2BA Haven City Views Steps to MagMile

Welcome to The Haven — a sunlit 3BR retreat in the heart of The Loop with skyline views and steps-from-the-park convenience. You're in expert hands: our Cloud9 team is a 7-year Superhost with 4,300+ five-star reviews across our Chicago portfolio.

Luxe

Apartment in Chicago

4.97 out of 5 average rating, 36 reviews

Luxury Downtown 4BR | Exclusive Design PH

Discover a premier Chicago experience in this luxury penthouse, ideal for travelers who value amazing views and a stylish stay. Our guest reviews prove it, with a 94% 5-star rating since 2023 for our stunning views and spotless cleanliness.