Vacation Rentals in Chicago

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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 €1,000 Nightly View Rental

River Style

Illinois, Chicago 5 guests 2 bedrooms 2 bathrooms Your trip to Chicago just got a whole lot sleeker with this bright apartment in River North. Perfectly set up for as a base for exploring the city, or as a home office, you’ll have plenty of places to... From €866 Nightly View Rental

Bluegill

Illinois, Chicago 3 guests 1 bedroom 1 bathroom This home in Chicago's chic River North neighbourhood is set just three blocks from the Magnificent Mile and six from the Museum of Contemporary Art. Design lovers and art aficionados will appreciate... From €395 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 €432 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 €984 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 €353 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 €926 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 €703 Nightly View Rental

Slice Of Sky

Illinois, Chicago 3 guests 1 bedroom 1 bathroom Surrounded by skyline and soaring scrapers, this city apartment boasts a central Chicago location that sets you up for an instant retreat. With artwork and windows out onto River North for decoration,... From €409 Nightly View Rental

Work & Play

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Work from home with ease at this stylish apartment in Chicago’s trendy River North neighbourhood. You’ll have plenty of options from where to set up shop – from the breakfast bar in the kitchen, to th... From €390 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