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Holiday rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

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Guest favourite
An inviting outdoor space features a sleek pool with a gentle water feature, surrounded by neat landscaping. The modern two-story structure rises in the background, complemented by a black umbrella positioned near the water's edge, creating a serene atmosphere for relaxation.
Guest house in Chicago
4.85 out of 5 average rating, 34 reviews

Andersonville Luxury Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

Guest favourite
Flat in Chicago
5 out of 5 average rating, 22 reviews

Upscale High-Rise Apt ยท Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Guest favourite
A modern living area is illuminated by natural light from large floor-to-ceiling windows. A comfortable gray sofa sits against one wall, accompanied by a coffee table. The open kitchen features a sleek marble countertop and stainless steel refrigerator, with minimalistic decor enhancing the ambiance.
Flat in Chicago
4.86 out of 5 average rating, 111 reviews

River North | Private Balcony With In&Out Parking

Enjoy a stylish experience at this centrally-located place โœจ. Stunning 1,000 square foot modern two-bedroom, one-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago ๐ŸŒ†. ๐ŸŒ‡ Rooftop Patio W/ BBQ ๐Ÿ– ๐Ÿš— Free In/Out Parking - 5 Mins Walk To Garage ๐ŸŒ… Private Balcony W/ Breathtaking Views ๐Ÿ›๏ธ 2 Bedroom | 1 Bathroom ๐Ÿ‘‘ 2 Queen Beds ๐Ÿ›๏ธ 1 Inflatable Airbed ๐Ÿ‘ถ Portable Crib ๐Ÿ“บ Netflix, Hulu, Disney Plus, and Prime subscription Included

Superhost
Flat in Chicago
4.82 out of 5 average rating, 1,354 reviews

Kasa | Walk to Lincoln Park Zoo | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favourite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Apartment in Chicago
4.96 out of 5 average rating, 151 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Top guest favourite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Flat in Chicago
4.95 out of 5 average rating, 112 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Superhost
Serviced apartment in Chicago
4.8 out of 5 average rating, 154 reviews

Level โ—† Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 โ€“ 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

Top guest favourite
Flat in Chicago
4.93 out of 5 average rating, 56 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the cityโ€™s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Top guest favourite
A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.
Flat in Chicago
4.99 out of 5 average rating, 140 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

Superhost
A private balcony is shown with a sleek black chair and small table. The view features a skyline of tall buildings under a colorful sunset sky, reflecting shades of pink and blue. A parking area can be seen below, filled with vehicles.
Flat in Chicago
4.82 out of 5 average rating, 51 reviews

Level Junior Two Bedroom Suite | Fulton Market

Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 177 reviews

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Top guest favourite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Apartment in Chicago
4.96 out of 5 average rating, 274 reviews

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

Popular amenities for Downtown Chicago holiday rentals

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