Holiday houses 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

Location · Value · Walkability

Warwick Allerton Hotel Chicago, Selected by hotel

The beautifully rejuvenated Warwick Allerton - Chicago offers charming accommodations at a storied Michigan Avenue address. Experience boutique ambience in one of The Windy City’s grandest hotels. From its inception in the early 1920’s, this timeless classic has been the standard bearer of Jazz Age style and sophistication and remains a noteworthy landmark in the Chicago skyline. Our stylishly designed rooms, renowned Warwick hospitality, and convenient location make it perfect for your stay.

Value · Location · River

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.

Location · Family · Checkout

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.

Family · Location · River

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!

Family · Location · TV

The Swissôtel Chicago, Selected by hotel

$35.22 Resort Fee to be collected on property Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park and has a state-of-the-art penthouse fitness center. The room may not look the same as the room in the photo as this room is run of house and selected by the hotel at check in.

Location · Value · Sleep quality

Private Room in Theatre District

Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Value · Location · Amenities

Level Studio | Fulton Market

Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.

Value · Location · Nearby

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.

Value · Location · Bathroom

Charming Historic Row Home | Lincoln Park

Experience historic charm and modern luxury in the heart of Lincoln Park. This updated 1870s row home features a private gated brick courtyard, chef’s kitchen with Wolf & Sub-Zero appliances, and full home automation. Unwind by the cozy wood-burning fireplace or retreat to 3 quiet bedrooms with newly renovated baths. Steps from Chicago’s best dining, boutique shopping, and transit—your perfect city getaway!

Location · Nearby · Sleep quality

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.

Value · Family · TV

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.

Location · Walkability · Accuracy