Holiday rentals in Chicago River

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Winter/Spring 2027. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, tall ceilings, and oversized windows, this spacious unit is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two

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.***

LIVN Millennium Park Downtown Chicago Prem Studio

Experience the best of Chicago from this stylish, newly renovated studio apartment 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 apartment 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

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.

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.

Little Italy Historic Restoration Row House

Location, location... fully rehabbed, historic 1884 row house w/2 Queen bedrooms and 2 bathrooms across from Arrigo Park in safe, quaint Little Italy. UIC campus, Rush University Medical Center and Illinois Medical District are blocks away. United Center is 17 minute walk and downtown sightseeing easily accessible by nearby public transportation. Fujitsu heating/AC units for individual comfort. Beautiful professionally maintained gardens outside your door.

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.

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.

Sentral Premium 2BR Apt South Loop Chicago

Feel at home amid the Chicago skyline. Designer details and mid-century style elevate everything you touch. An all-in-one living area gives you plenty of room to live and work. The fully equipped kitchen features marbled quartz countertops and a gas range. Please note that layout, furnishings, and views may vary by unit. A $500 credit card authorization applies at check-in and is released at checkout.

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.

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.