Holiday houses in Chicago River

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Top-rated holiday rentals in Chicago River

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Top Guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park
4.99 out of 5 average rating, 109 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Superhost
A modern living area features a dark gray sofa, complemented by decorative pillows and a coffee table. Large windows provide ample natural light and city views, while plants add a touch of greenery. The space is designed with clean lines and a neutral palette.
Apartment in Chicago Loop
4.77 out of 5 average rating, 230 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, tall ceilings, and oversized windows, this spacious unit is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two

Guest favourite
Apartment in Lincoln Park
4.78 out of 5 average rating, 287 reviews

Rare 1BR Lincoln Park Apt, close to everything!

Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

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.
Apartment in Downtown Chicago
4.98 out of 5 average rating, 161 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. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Guest favourite
Apartment in Chicago Loop
4.79 out of 5 average rating, 33 reviews

LIVN Millennium Park Downtown Chicago Prem Studio

Experience the best of Chicago from this stylish, newly renovated studio apartment at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This apartment offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended

Apartment in Downtown Chicago
4.89 out of 5 average rating, 9 reviews

Kasa Lake Shore Chicago | Studio King

Kasa Lake Shore Chicago offers spacious, furnished apartments for short and extended stays, steps from Lake Michigan, Navy Pier, and the Magnificent Mile. Each tech-enabled unit has a full kitchen, in-unit laundry, and access to co-working areas, offering more space than a hotel for business and leisure travelers. Check-in starts at 4pm and can be done contactless from your phone, or in person at our front desk, open daily from 11am to 730pm. Text us anytime for Virtual Front Desk support.

Superhost
A bright bedroom features a spacious bed with crisp white linens, complemented by an abstract wall art piece. A wooden nightstand with a lamp is positioned beside the bed. Large windows provide natural light, showcasing views of the city beyond.
Apartment in Downtown Chicago
4.81 out of 5 average rating, 304 reviews

Kasa | Explore the Neighborhood-Mag Mile | 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.

Top Guest favourite
Apartment in South Side
5.0 out of 5 average rating, 5 reviews

European Coziness in Bronzeville

Brand-new luxury 3BR, 2BA top-floor apartment in the heart of historic Bronzeville. Designed for families, groups, and business travelers, it features stylish interiors, a fully equipped kitchen, spacious living area, and premium finishes throughout. Minutes from McCormick Place (3.4 mi), Downtown, Hyde Park, museum of Science and Industry, University of Chicago, and the lakefront. Experience comfort, space, and one of Chicago's most vibrant neighborhoods.

Hotel room in Chicago Loop
4.82 out of 5 average rating, 144 reviews

City king

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

Superhost
Apartment in Downtown Chicago
4.79 out of 5 average rating, 163 reviews

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 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.

Guest favourite
Apartment in Chicago Loop
5.0 out of 5 average rating, 12 reviews

Riverfront Views - Smart Home - Simple Check In

Luxury smart home in a high-rise designed for corporate stays and business travelers. This fully furnished unit features seamless smart home controls, high-speed WiFi, and designed for comfort. Located in the heart of downtown, steps from the river, dining, and nightlife. Ideal for professionals in town for training, projects, or short-term assignments.

Top Guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in West Town
4.97 out of 5 average rating, 920 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Popular amenities for Chicago River holiday rentals

Frequently Asked Questions

  • Where is Chicago River located?

    The Chicago River flows through the heart of Chicago, connecting Lake Michigan to historic neighborhoods, business districts, and cultural spaces. Its route is visible near downtown and several waterfront areas.

  • When is the best time to visit Chicago River?

    Late spring through early fall is often recommended for walks or river activities along the Chicago River, as temperatures tend to be comfortable and greenery abundant. Winter visits can bring scenic views, though waterfront winds may make it feel colder.

  • What are some things to do near Chicago River?

    You can explore architectural boat tours, stroll the scenic Riverwalk, or visit nearby art installations and public parks along the Chicago River. Neighborhood dining, shopping, and cultural destinations around the riverfront are frequently suggested for diverse experiences.

  • How is the weather near Chicago River?

    Weather near the Chicago River varies from chilly winters around 19–38°F (−7–3°C), often with snow, to warm summers reaching 85°F (29°C) with moderate humidity. Spring and fall typically bring milder temperatures and changing foliage along the waterfront.

Destinations to explore