Luxury rentals in Downtown Chicago

Large Luxury House in River North!

Centrally located River North Penthouse in boutique building has everything you would want in city living. 2-story condo ALL 3 bedrooms featuring en-suites and an additional 1/2 bath. Large living room w/fireplace expands on to the outdoor deck with beautiful built-in grill, 2nd story features 2 bedrooms and a bright sun room with sofa bed. Spacious primary cozy fireplace along with steamed shower and jacuzzi tub. So much more with this luxury style living. Steps to all River North has to offer!

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!

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! ✨

1,622SqFt Penthouse | 69th Flr Views | Sleeps 4

Wake up on the 69th floor to the entire Chicago skyline glowing beneath you — inside the biggest 2-bedroom penthouse in the city. At 1,622 sq ft, 'Skyfall' gives your group room most hotels charge four times more for. Hosted by Cloud9 — 4.9 stars across 5,000+ reviews, specializing in luxe penthouse stays. Floor-to-ceiling windows and 80,000+ sq ft of building amenities included. Book the view — and the space — most people only see from postcards.

Luxury PH: Panoramic Views + Prime Location

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.

Architect-Designed 3BR Oak Park Flat

Experience historic Oak Park in our beautifully renovated 3-bedroom apartment. Blending 1920s charm with modern luxury, this space comfortably fits families or groups. Features a dedicated workspace, new kitchen, and a shared roof deck. Located steps from the Green Line, offering a quick, direct ride to downtown Chicago. Perfect for exploring both Oak Park's cultural gems and the Windy City.

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.

Skyline View Duo for Groups: Unmatched Luxury Stay

Discover 'The Seven,' an exclusive offering of two same-floor penthouses designed to provide your group with a seamless and stylish Chicago stay. Join over 2,000 happy guests and book with confidence, knowing our commitment to excellence is proven by years of 5-star 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.

Luxury Penthouse: Iconic Views + Exclusive Comfort

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.