Vacation Rentals in Chicago

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The Windy City Retreat

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining an... From €523 Nightly View Rental

Culture Haven

Illinois, Chicago 12 guests 4 bedrooms 4 bathrooms Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City. Experience traditional Chicago his... From €1,674 Nightly View Rental

Chicago Chill Pad

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Wind... From €802 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 €2,118 Nightly View Rental

Charming Chicago Charm

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The loc... From €546 Nightly View Rental

Elevated Luxe

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Welcome to The Lincoln! To ensure safety, all guests must pass our screening process and provide proper ID. A $1,000 security deposit is required for your booking, accepted on Major Credit Cards only,... From €654 Nightly View Rental

Skyline Reverie

Illinois, Chicago 7 guests 3 bedrooms 3 bathrooms High above River West, this spectacular home with skyline views invites you to experience Chicago at its most inspiring. Floor-to-ceiling windows keep the city close at every moment, while the balcony... From €1,046 Nightly View Rental

Windy City Wonder

Illinois, Chicago 12 guests 6 bedrooms 6 bathrooms Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick. In each home expe... From €1,834 Nightly View Rental

Metropolis Respite

Illinois, Chicago 7 guests 3 bedrooms 3 bathrooms Welcome to The Willis! To ensure safety, all guests must pass our screening process and provide proper ID. A $2,500 security deposit is required for your booking, accepted on Major Credit Cards only,... From €1,225 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 €787 Nightly View Rental

Self-Catering Chicago

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Listing 1-10 of 36 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