Holiday houses in Chicago River

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Top-rated holiday rentals in Chicago River

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Superhost
Apartment in The Loop
4.86 out of 5 average rating, 148 reviews

LIVN Millennium Park Downtown Chicago 1 BR

Experience the best of Chicago from this stylish, newly renovated 1-bedroom 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 1 bedroom 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 stays. Enjo

Apartment in Downtown Chicago
4.67 out of 5 average rating, 27 reviews

Kasa Lake Shore Chicago | Two Bedroom King & Queen

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 serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago
4.81 out of 5 average rating, 1041 reviews

Kasa | Views from your Private Balcony | 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.

Superhost
A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.
Apartment in The Loop
4.81 out of 5 average rating, 355 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Guest favourite
A contemporary hotel room is presented, featuring a spacious bed with soft linens. A striking blue wall mural adds a modern touch. Natural light enters through a large window, illuminating the wooden floor and sleek furniture, including a bedside table and desk.
Hotel room in The Loop
4.91 out of 5 average rating, 76 reviews

Private Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Superhost
A modern studio apartment is featuring a spacious bed with white linens, positioned next to a cozy gray sofa. A flat-screen television is mounted on the wall, with framed artwork adding subtle décor. Light wood cabinetry complements the neutral color scheme.
Apartment in West Loop
4.76 out of 5 average rating, 67 reviews

Level Studio | Fulton Market

Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.

Hotel room in The Loop
4.83 out of 5 average rating, 152 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.

Home in Lincoln Park
5.0 out of 5 average rating, 3 reviews

Charming Historic Row Home | Lincoln Park

Experience historic charm and modern luxury in the heart of Lincoln Park. This updated 1870s row home features a private gated brick courtyard, chef’s kitchen with Wolf & Sub-Zero appliances, and full home automation. Unwind by the cozy wood-burning fireplace or retreat to 3 quiet bedrooms with newly renovated baths. Steps from Chicago’s best dining, boutique shopping, and transit—your perfect city getaway!

Superhost
A modern café space features a stylish counter with intricate tile work, where a staff member assists a guest. A well-groomed dog on a leash stands attentively beside the guest. Coffee machines and bottled beverages are visible in the background.
Hotel room in Downtown Chicago
4.77 out of 5 average rating, 631 reviews

Close to Navy Pier + Restaurant. Bar. Gym.

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Guest favourite
Apartment in The Loop
5.0 out of 5 average rating, 15 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.

Superhost
Hotel room in The Loop
4.82 out of 5 average rating, 710 reviews

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Hotel room in The Loop
4.74 out of 5 average rating, 77 reviews

Deluxe two queens - city view

Deluxe two queens city view offers a stylish retreat on a high floor with city views, two queen beds, plush bedding, and modern furnishings. Major amenities include a sofa bed, armchair, table, chair, mini fridge, flat screen TV, laptop size safe, coffee maker, and wifi for a comfortable stay.

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