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 €786 Nightly View Rental

Solo Breeze

Illinois, Chicago 2 guests 1 bedroom 1 bathroom This studio apartment in stylish River North is perfectly equipped for both work and play. Spend a day at your home office with plenty of seating options – from the desk in the bedroom by a window wit... From €229 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 €700 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 €412 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 €412 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 €246 Nightly View Rental

Savings Account

Illinois, Chicago 3 guests 1 bedroom 1 bathroom Are you a solo traveller or couple looking to stay in Chicago? Bookmark this page right now: you’ve found the right home-from-home with this one-bed in the arty River North district. It's close to Oak... From €353 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 €354 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 €840 Nightly View Rental

Monday Night

Illinois, Chicago 3 guests 1 bedroom 1 bathroom Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-... From €554 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