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Self-Catering Chicago, Illinois

Top 10 Holiday Homes in Chicago

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... View Rental

Chicago Charisma

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of... From €525 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 €1,887 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

The Lion

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms This home is the perfect place to relax and enjoy your stay in Chicago. The home is located in the Gold Coast neighborhood, which is known for its luxury shops, fine dining, and lake Michigan charm. T... From €833 Nightly View Rental

Chicago Morning

Illinois, Chicago 8 guests 4 bedrooms 3 bathrooms Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is centra... From €1,425 Nightly View Rental

All Things Glow

Illinois, Chicago 3 guests 2 bedrooms 1 bathroom This apartment in Chicago's Hyde Park is positively flush with luxury touches. We love the trendy, timeless design, which merges mid-century pieces with a modern flair. Take, for instance, the custom-... View Rental

Self-Catering Chicago

Listing 1-7 of 7 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.