Vacation Rentals in Chicago

Home USA Illinois Chicago

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 €1,297 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 €758 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 €2,206 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 €2,608 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 €659 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 €658 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 €623 Nightly View Rental

The Heart of the Loop

Illinois, Chicago 16 guests 8 bedrooms 8 bathrooms Welcome to a holiday getaway nestled right in the heart of Chicago’s vibrant Financial District. Just steps from iconic attractions, revel in the rich history of the city through its grand architectur... From €6,156 Nightly View Rental

The Urban Villa

Illinois, Chicago 6 guests 2 bedrooms 2 bathrooms A striking interplay between tradition and trend elevates this property nestled within the vibrant Streeterville neighbourhood. Combining nostalgic tales of Chicago's history with an undercurrent of w... From €330 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 €580 Nightly View Rental

Self-Catering Chicago

«
1
2
3
4
Next »

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