Luxury rentals in Chicago

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Top-rated luxury holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

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Luxe

The spacious living area features a dining table with black chairs and a wooden tabletop, complemented by an inviting lounge area with a large sofa and accent chairs. Large windows allow natural light to illuminate the room, enhancing its modern design.

Apartment in Gold Coast

4.88 out of 5 average rating, 33 reviews

Luxury Designer Penthouse|Private Deck|Gold Coast

BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. In a completely redeveloped luxury brownstone, your 3 bedroom/3 bathroom penthouse offers ultra high-end appliances, design, and finishes, with two private patios/decks (truly unique amenity in Chicago) and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between!

Luxe

A spacious living area is featured, showcasing a modern sectional sofa adorned with cushions. A wooden coffee table sits centrally, accompanied by decorative items. The open layout includes a dining area with circular chairs and a large window allowing natural light to fill the room.

Condo in Uptown

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 Loop

4.73 out of 5 average rating, 11 reviews

PH w/ Bean & Lake Views, An Elite Stay

For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The Bean & Millennium Park views and access to a private amenity floor. It's a proven elite experience, with a remarkable 9 out of 10 recent guests leaving a 5-star review.

Luxe

A spacious living area is showcased, featuring a modern sectional sofa with neutral tones. A sleek kitchen island, equipped with high-end appliances, complements a dining table surrounded by colorful chairs. Large windows allow ample natural light and provide views of the city beyond.

Apartment in Chicago Loop

4.79 out of 5 average rating, 24 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.