Apartment holiday rentals in Chicago River

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Top-rated apartment rentals in Chicago River

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Flat in Chicago
5 out of 5 average rating, 315 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Superhost
A modern living space features a combination of comfortable seating arrangements, including a sleek sofa and various chairs. Bright natural light floods the area, highlighting a stylish dining table and a mounted television. Contemporary art and decorative elements add to the inviting ambiance.
Flat in Chicago
4.8 out of 5 average rating, 370 reviews

Modern River West 2 Bed 2 Bath-Steps to Blue Line

Enjoy Urban Living in my 2 bed 2 bath River West apartment. Located in a beautiful and secure new building, relax in a tranquil modern space with all of the conveniences of home. You'll be steps from the Grand blue line station and a quick walk to award-winning restaurants in trendy Fulton Market and Randolph Street. Downtown Chicago is just a short drive or train ride away. You won't run out of accessible Chicago charm here - and the proximity to the Loop really can't be beat. Book today!

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, 341 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 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.
Flat in Chicago
4.81 out of 5 average rating, 294 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 favourite
A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.
Flat in Chicago
4.89 out of 5 average rating, 289 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Top guest favourite
The living and dining area is designed with high ceilings and an open layout. A sofa is paired with a modern armchair, while a wooden dining table is surrounded by stylish chairs. Large windows bring in natural light, highlighting warm wood floors and minimal decor.
Flat in Chicago
4.94 out of 5 average rating, 287 reviews

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely in the bedrooms.

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, 115 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.

Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 204 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***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
Flat in Chicago
4.87 out of 5 average rating, 100 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.

Guest favourite
A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.
Flat in Chicago
4.94 out of 5 average rating, 105 reviews

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

Guest favourite
A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.
Flat in Chicago
4.92 out of 5 average rating, 181 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.

Superhost
A multi-story building is prominently displayed at the corner of an urban intersection. Architectural features include a distinct facade with vertical elements and large windows. Surrounding high-rise buildings and city infrastructure create a lively backdrop, reflecting the vibrant atmosphere of downtown Chicago.
Flat in Chicago
4.82 out of 5 average rating, 103 reviews

South Loop Studio Hotel (309)

Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!

Popular amenities for Chicago River apartment rentals

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