Holiday rentals in Chicago River

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

The Picasso: #1 Chicago Location

Welcome to The Picasso on Lincoln Park… Chicago’s BEST location! Steps away from the beach, zoo, cafes, nightlife, and easy Uber access for short 5-min rides to Michigan Ave & Wrigley Field! Recent rehab with charming art house decor. Professionally managed and sanitized. Historic landmark building, with a junior-suite feel (500 sqft), lofted open-air bedroom with queen bed, 3rd floor. WiFi, shared coin operated laundry, excellent heat/AC, free street parking or paid parking lot 2 blocks away.

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. The pool and spa are heated heated through 12/31.

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

Kasa | Walk to Lincoln Park Zoo | 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.

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!

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, if ever, in the bedrooms.

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.

Level Two Bedroom Suite | Fulton Market

Our Two Bedroom Suites are spacious and sophisticated boasting up to approximately 1,150 sqft of modern living space. Make a home-cooked meal in your fully equipped kitchen, host friends in your open concept living and dining area, and take in the city views on your open-air balcony. All suites also feature in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, and complimentary Wi-Fi.

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. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

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.

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.