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 · Family · Amenities

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

Family · Location · Check-in

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.

Family · Location · Laundry

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Family · Location · Outdoor spaces

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.

Location · Value · TV

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!

Value · Family · Comfort

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 · Nearby

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 · Location · Checkout

Standard Room with King Bed

Enjoy a spacious deluxe room with a king bed, premium bedding, and ergonomic workspace for added comfort. The room features air conditioning, free wifi, a flat-screen smart tv, and a nespresso coffeemaker. Thoughtful bathroom amenities and dog-friendly options make your stay convenient and relaxing. This is a non-smoking room designed for a seamless experience.

Value · Location · Comfort

Elegance and comfort in Gold Coast neighborhood

Less than a mile from Oak Street Beach and the lakefront, our hotel offers elegance and comfort in the midst of top city attractions. Shopping and fun at the Magnificent Mile or Navy Pier, or a visit to the Lincoln Park Zoo are all within two miles. Our on-site restaurants, event room with natural light, and fitness center complete your stay.

Value · Location · Amenities

Level One Bedroom Suite | Fulton Market

One Bedroom Suites offer approximately 650 sqft of living space and boast fully equipped kitchens, living room with sofa bed, spa-inspired bathroom, and separate bedroom with king bed and open-air balcony. All suites feature in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, and complimentary Wi-Fi.

Location · Value · Nearby

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Location · Family · Outdoor spaces