Vacation Rentals in Chicago

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Chicago Chic

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away. When you’... From €590 Nightly View Rental

The Essential Stay

Illinois, Chicago 16 guests 8 bedrooms 8 bathrooms Consisting of four self-contained apartments across the same building, this Chicago setup is purpose-built for large groups who want to be together without living in each other's pockets. You're right... From €2,312 Nightly View Rental

West Wing

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms As serviced apartments in Chicago go, there don’t come much better than this. A great option for a longer stay in the city, there’s a shared gym for keeping on top of fitness and heaps of communal lou... From €477 Nightly View Rental

The West-Loop Wavelength

Illinois, Chicago 17 guests 8 bedrooms 8 bathrooms Welcome to a unique urban retreat, igniting the senses, and beckoning guests to indulge in the transformative charm of West Loop. Once an industrial essence, it has blossomed into a locus of gastronom... From €2,456 Nightly View Rental

The West Place

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms Overlooking the Gold Coast of Chicago, this home is as desirable as its location. You’ll be gifted with stunning skyline views, a private terrace and an array of home comforts. Coffee and tea are prov... From €895 Nightly View Rental

New Pathways

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms You’ll be swept off your feet by this penthouse apartment. From the stunning views to the thoughtful design, every detail has been considered to bring ease to your city stay. There’s a private terrace... From €1,025 Nightly View Rental

Elevated Luxe

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms You’ll want for nothing at this West Loop serviced apartment complex. There’s a shared outdoor pool and terraces, a state-of-the-art health club and a cinema screening room. Here for work? The dedicat... From €637 Nightly View Rental

Italian Villa Immersion

Illinois, Chicago 8 guests 3 bedrooms 2 bathrooms Immerse yourself in the experience that is The Zeus, centrally positioned in the exciting Streeterville neighborhood. Here, a unique blend of classic allure fuses with an internationally inspired desi... From €1,062 Nightly View Rental

Chicago Vista

Illinois, Chicago 6 guests 2 bedrooms 2 bathrooms Step inside The Leto, where classic charm mingles with vibrant culture in the bustling Streeterville neighborhood of Chicago. This locale promises an immersive experience into not only traditional Chi... From €934 Nightly View Rental

Metropolis Retreat

Illinois, Chicago 18 guests 9 bedrooms 6 bathrooms Travelling with a big crew? This trio of downtown Chicago penthouses makes it a breeze. With nine bedrooms spread across three apartments, everyone gets space to themselves without missing out on the... From €3,908 Nightly View Rental

Self-Catering Chicago

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Listing 1-10 of 34 Top Holiday Rentals

Vacation Rentals Chicago Top Destinations

Holiday Homes & Accommodation Chicago

Chicago or popularly known as ‘The Windy City' is located on Lake Michigan in Illinois, and is one of the largest U.S. cities and a popular holiday destination. Stretch your neck towards the sky and take in the impressive skylines filled with skyscrapers and outstanding architecture.

Immerse yourself in the popular Art culture by visiting the Art Institute of Chicago, or walk through Millennium Park or even visit Lincoln Park Zoo. Chicago is famed for some delicious comfort food – sample some Chicago-style hot dogs and a deep-dish Chicago-style pizza.

Self-Catering Chicago, Illinois

Top 10 Holiday Homes in Chicago