Vacation Rentals in Chicago

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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 €484 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 €938 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 €287 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 €359 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 €900 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 €369 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 €326 Nightly View Rental

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 €1,760 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 €306 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 €269 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