Vacation rentals in Chicago River

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Top-rated vacation rentals in Chicago River

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Guest favorite
Apartment in Chicago Loop
4.88 out of 5 average rating, 145 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

Superhost
Home in South Side
4.91 out of 5 average rating, 32 reviews

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

Top guest favorite
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, 163 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 favorite
Apartment in Downtown Chicago
4.79 out of 5 average rating, 24 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.

Top guest favorite
Home in Humboldt Park
5.0 out of 5 average rating, 32 reviews

Beautifully Renovated Loft-Style Coach House

Stay at this beautifully renovated all-brick coach house in lovely Humboldt Park/West Town! Once a cigar factory in 1908, this unique space has been fully rehabbed & restored for a charming and industrial stay. Its an open-concept loft-style house, and is entirely private - no neighbors above or below you. It boasts a balcony and a large rooftop deck with gorgeous city skyline views. We are proud to be a family-owned rental and take care and pride in this special space! Welcome to Chicago!

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, 1039 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 Chicago Loop
4.81 out of 5 average rating, 354 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!

Top guest favorite
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.
Apartment in Downtown Chicago
4.95 out of 5 average rating, 298 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.

Guest favorite
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.
Apartment in West Side
4.95 out of 5 average rating, 130 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 favorite
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.
Apartment in Downtown Chicago
4.92 out of 5 average rating, 186 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 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, 627 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.

Top guest favorite
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 vacation 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