Vacation Rentals in Chicago

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Easel And Brush

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest conce... From €574 Nightly View Rental

Panorama Place

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the m... From €963 Nightly View Rental

Running Loops

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re wit... From €824 Nightly View Rental

I’m With The Band

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms This bright apartment located in the music hub of South Loop is perfect for a family holiday in Chicago. You’ll have options for outings galore, with jazz bars and restaurants at your doorstep, as wel... From €961 Nightly View Rental

Designed For Life

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms It doesn’t matter if you’re in Chicago for work, rest or play at this two-bed in the hip River North district. The apartment has all that a family or small group of friends would need for a stay in t... From €609 Nightly View Rental

Skyscraper

Illinois, Chicago 3 guests 1 bedroom 1 bathroom Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district... From €382 Nightly View Rental

Solo Bird

Illinois, Chicago 2 guests 1 bedroom 1 bathroom This stylish River North studio is the perfect find for a quick business trip or city break in Chicago. Perfectly set up to work from home – you can sip a coffee at the chic breakfast bar while readin... From €289 Nightly View Rental

On Cloud Nine

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the mo... From €346 Nightly View Rental

Swing Swing

Illinois, Chicago 6 guests 3 bedrooms 2 bathrooms Jazz about town from this charming apartment in Chicago’s South Loop – a music hub filled with live venues, restaurants and bars. Grab a morning pick-me-up at the in-building gourmet coffee shop befor... From €980 Nightly View Rental

Local Colour

Illinois, Chicago 4 guests 2 bedrooms 2 bathrooms Fancy trying out the lifestyle of a Chicagoan for a bit? Look no further than this cool River North apartment, which will make you feel right at home in one of the city’s most desirable districts. Sta... From €386 Nightly View Rental

Self-Catering Chicago

Listing 1-10 of 23 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