Vacation Rentals in Chicago

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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 €326 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 €746 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 €746 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 €410 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 €698 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 €981 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 €366 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 €280 Nightly View Rental

Checking Account

Illinois, Chicago 2 guests 1 bedroom 1 bathroom Get out your Chicago apartment checklist and be prepared to get ticking as this apartment has all you need for your time in the Windy City. You'll find fantastic views through the floor-to-ceiling win... From €272 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 €543 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