Luxury rentals in The Loop

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Top-rated luxury vacation rentals in The Loop

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

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Luxe

Apartment in Downtown Chicago

4.92 out of 5 average rating, 48 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

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 The Loop

4.83 out of 5 average rating, 18 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

Apartment in The Loop

New place to stay

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 The Loop

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.