Holiday rentals in Chicago River

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Top-rated holiday rentals in Chicago River

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Top guest favourite
Private room in Chicago
4.94 out of 5 average rating, 139 reviews

Cozy Room for One In The Company of Cats -Blueline

Great location for solo adventurers and business travelers. Easy access to public transportation, 1-90 expressway, divvy bikes and bike lanes. Charming, private room in a vintage home and neighborhood. My home is also home to four felines, so being a big fan of cats is must! Easy, free street parking in front of the house or short walk from the Addison Blueline stop - just 20 minutes to downtown or O’Hare! Wrigley Field is just 3 miles east! The Addison 152 bus takes you right to Wrigley Field.

Serviced apartment in Chicago
4.5 out of 5 average rating, 10 reviews

Experience Chicago! Full Kitchen, Free Breakfast!

The hotel is excellently situated in downtown Chicago. There are many popular attractions within easy reach of the property doors. Such as the iconic Magnificent Mile, known for its shopping, dining, and entertainment options. Guests may visit the historic Navy Pier, bustling with activities for all ages, or admire the city's skyline from the 360 Chicago Observation Deck. Discover world-class art at the Museum of Contemporary Art or appreciate the beauty of Lake Michigan from Ohio Street Beach.

A modern studio apartment is featured, showcasing an open layout with a comfortable orange sofa centered against wooden cabinetry. The kitchen area includes stainless steel appliances and a sleek countertop, while a spacious bed is positioned adjacent, contributing to the functional living space.
Apartment in Chicago
4.77 out of 5 average rating, 115 reviews

Cabin 102 at 747 Lofts

Unique space set up to be ADA accessible with wide walkways, step-free shower, bathroom grab bars, and open space beneath the sink! This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home.

Guest favourite
The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.
Flat in Chicago
4.8 out of 5 average rating, 368 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Guest favourite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Apartment in Chicago
4.94 out of 5 average rating, 276 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

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.
Flat in Chicago
4.82 out of 5 average rating, 342 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!

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.
Flat in Chicago
4.81 out of 5 average rating, 1,002 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.

Top guest favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Chicago
4.96 out of 5 average rating, 287 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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, 116 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.

Top guest favourite
Two hanging chairs are positioned on a covered patio, surrounded by lush greenery and decorative plants. A small garden structure adds privacy, while the floor features a vibrant red surface. Ambient light filters through the overhead structure, creating a relaxed outdoor space.
Home in Chicago
4.96 out of 5 average rating, 51 reviews

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!

Guest favourite
Flat in Chicago
4.87 out of 5 average rating, 110 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 city’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
Flat in Chicago
5 out of 5 average rating, 15 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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.

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