Vacation rentals in Chicago River

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Top-rated vacation rentals in Chicago River

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An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.

Guesthouse in Chicago

4.86 out of 5 average rating, 444 reviews

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

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.

Apartment in Chicago

4.8 out of 5 average rating, 304 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.

Superhost

The bright living area is enhanced by large windows allowing natural light to fill the space. A blue sectional sofa and two armchairs provide comfortable seating. A ceiling fan is visible above, and a TV is mounted on the wall. The dining area is seen in the background.

Apartment in Chicago

4.81 out of 5 average rating, 36 reviews

Spacious & Elegant N Side Apt Near Beach & Transit

This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

Guest favorite

A wall-mounted shelf displays a selection of games and activities. Notable items include a colorful game box labeled 'Charades', along with stacks of miscellaneous game pieces. Above the shelf, the word 'PLAY' is spelled out using wooden blocks, adding a playful touch to the space.

Townhouse in Chicago

4.88 out of 5 average rating, 366 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS/PERMIT VISITORS. Please agree per message to confirm

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 Chicago

4.82 out of 5 average rating, 236 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.

Guest favorite

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

Loft in Chicago

4.99 out of 5 average rating, 116 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Top guest favorite

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.

Guesthouse in Chicago

5 out of 5 average rating, 12 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.

A spacious bedroom is highlighted by a large bed with crisp white linens. Flanking the bed are two wooden nightstands, each topped with unique lamps. A cozy bench is positioned at the foot of the bed, and large windows provide natural light.

Apartment in Chicago

4.71 out of 5 average rating, 316 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Superhost

A bright studio apartment features large windows allowing natural light to fill the space. A cozy bed is positioned beside a small dining table and chairs, while a comfortable sofa is present for relaxing. A television is mounted on the wall for entertainment.

Condo in Chicago

4.77 out of 5 average rating, 195 reviews

Cabin 301 at 747 Lofts

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. One of the best pizza spots in Chicago is only steps away!

Top guest favorite

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

5 out of 5 average rating, 5 reviews

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just two blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! 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!

The spacious living area features high lofted ceilings and exposed brick walls. A large flat-screen TV is mounted on the wall, and two stylish pendant lights hang from the ceiling. The seating area includes a coffee table, with a soft area rug placed centrally.

Loft in Chicago

4.74 out of 5 average rating, 27 reviews

Amazing 2500 sq/ft Loft & Bungalow in Lincoln Park

This is a 2500 sq/ft loft in Lincoln Park, one of the best neighborhoods in Chicago & most centrally located. 1 private room, lofted (open) ceilings, 1 bathroom & a 2nd open layout bungalow room w/ curtains - All spaces are huge from bedroom, kitchen to living room! There's tons of free street parking & 5-10 min Uber to Art Institute, The Bean, etc. --

Guest favorite

A spacious bedroom features a large bed with a dark upholstered headboard, flanked by matching nightstands. A vintage-style lamp sits on a side table, and two leather stools are positioned at the foot of the bed. Richly textured walls and large windows create a cozy ambiance.

Apartment in Chicago

4.84 out of 5 average rating, 79 reviews

MAG MILE Designer Flat - Steps to the Lake!

A design lover's dream. Spend your next trip (or staycation) in a beautifully remodeled luxury studio in Chicago's Gold Coast neighborhood. This listing is for a private studio in a multiple-unit building. ✔ Safe and vibrant neighborhood. ✔ Steps from Michigan Avenue, luxury shops, and the Lake ✔ Convenient parking options nearby. ✔ Easy self-check-in.