Vacation Rentals in Chicago

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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 €606 Nightly View Rental

The West Wind Charm

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Welcome to a dazzling retreat in the heart of West Loop. A vibrant ambience invites you to immerse yourself, enveloped by the rhythm of the city's live music and savory aromas from nearby culinary gem... From €630 Nightly 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 €615 Nightly View Rental

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 €510 Nightly View Rental

Charming River Retreat

Illinois, Chicago 14 guests 6 bedrooms 6 bathrooms Welcome to a true haven in the heart of Chicago's vibrant River West neighborhood. Surrounded by trendy restaurants, bars, and shops, this elegant and modern retreat offers a tranquil escape from the... From €2,982 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 €726 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 €2,074 Nightly View Rental

WindyCity Wonders

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Immerse in the life of West Loop Gate, Chicago at this lovely rental! As a former industrial area turned dining and nightlife hub, the scene offers a unique juxtaposition. The streets dance with an ar... From €1,324 Nightly View Rental

Urban Vistas

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there. Part of a high-end serviced apartment... From €623 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 €5,765 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